Winnipeg State of Mind – Top 100 Winnipeg Hip-Hop Songs

by Nigel Webber

“Success is a gift, I hope you enjoy your present” – B-Flat

    Earlier this year a group of writers from Manitoba’s most prominent newspaper compiled a list of the best songs to ever come out of this city and province. Of the 150 songs those writers chose, only five were rap songs. Winnipeg hip-hop deserves more than just 3% of a list. We deserve our own fucking list: The Top 100 Winnipeg Hip-Hop Songs, according to myself alone.

    As I actively dig into the history of Winnipeg hip-hop music for my forthcoming book, “Gritty City: An Oral History of Winnipeg Hip-Hop Music,” I know the hard work and dedication that generations of rappers, producers, DJs have put into this city. Let this list prove that there is an extensive and proud history of hip-hop music from right here in Winnipeg. Let it also serve as a tool for the younger generation: follow the roadmap I have provided here, learn your history, listen to those who have come before you. There’s no longer an excuse for not knowing. 

    The Top 100 is very much informed by the research and interviews I’ve done for “Gritty City,” including with many of the artists featured below. I’ve presented the list in chronological order to illustrate that each song, each album is standing on the shoulders of the music that came before it. No top ten’s here. But there are bangers, bars, singing, boom-bap, trap, love songs, posse cuts, deep digs, classics and story tracks; a flavour for every rap fan. 

    In order to qualify at least one of the major contributors to the song had to have been living in Winnipeg at the time of the recording or release. For example, while I love the album “Nothing Is Cool” by mcenroe and Birdapres, it was not eligible because even though both rappers lived in Winnipeg at different times, they were living in Vancouver at the time of that record. 

While this list attempts to be comprehensive, early Winnipeg rap was often not recorded or released. As influential and important as they are to the evolution of Winnipeg hip-hop, I can’t include early groups like the Vicious Three and Hard Edge Posse on the Top 100 because they never released any music officially. I am also aware of albums that exist, but I have not been able to track them down. So, if you’ve got that Last Crew album or the Black Alien Brother tape, holla at me.

Main Street – J-Style, DJ Bunny, Avon T

Released in 1988 as a video single.

Winnipeg’s hip-hop scene slowly built itself up over the course of the 1980s, with DJ Bunny playing a big part in that development. It took until 1988 to get the first official recording of Winnipeg rap with the video for “Main Street” by J-Style featuring DJ Bunny on back-up vocals and scratches and Avon T on the guitar. While the video was submitted to Much Music, it only ever received airplay on VPW’s “Spotlight” hosted by DJ Bunny, Avon T and Mr. Cee. J-Style, better known as rock ‘n roller Jay Willman, raps about the street-level devastation of Main St circa the late 1980s. The video helps paint a picture of Winnipeg’s Main St. that has largely disappeared under the thumb of gentrification. 

Jus’ Talkin’ – State of Mind

Released in 1992 on the “Jus’ Talkin'” cassingle.

Winnipeg’s first physical release of rap music came in the form of State of Mind’s 1992 cassingle for “Jus’ Talkin'” with the remix “Street Talking” on the B-side. The songs were produced and released by LRN Records, who ended up scamming the young group out of grant money awarded to make the project. The resulting beat sounds somewhat dated to modern ears and was even out of step with contemporaneous sounds. Despite not having a very hip-hop beat, rapper Chris Knight (MC Escalade) really demonstrates why he is still acknowledged as one of the top rappers of that era. The songs subject matter addresses the aftermath of the Rodney King verdict and the ensuing uprising in LA almost in real time, the cassette came out less than six months later.

Space Pt. III – Farm Fresh

Released in 1994 on “The Space EP”

Winnipeg had a strong hip-hop scene already, but it took three dudes from Brandon to come in and blow it all up in the mid-’90s. Farm Fresh’s 1994 “The Space EP” is Winnipeg’s first independent tape release, with everything from production to manufacturing happening within the group of Roddy Rod the Microphone God (mcenroe), Boba Phat tha Bootie Hunta (DJ Hunnicutt) and the Perpetual Rhyme Machine (Pip Skid). “The Space EP” also marks the beginning of a long Winnipeg tradition of rapping about off-the-wall, non-typical topics for rap songs, in this case being abducted by aliens. 

Ruff Draft – Mood Ruff ft. Roddy Rod

Released in 1995 on “Maxim”

With Farm Fresh leading the way, the newly formed label of Peanuts & Corn put out their next group, Mood Ruff. The duo of Dazol the Daydream Fiend (Odario Williams) and Spitz the Microphone Hitta (DJ Dow Jones) released “Maxim” in early ’95, produced entirely by mcenroe. Generally a fairly light and fun record, “Ruff Draft” keeps that theme but centres it around the concept of needing to come up with a song for a show that’s in two days. The song also marks the first instance of mcenroe giving away a hot beat to a group he’s producing, with the one condition that he gets to rap on it. 

Ill Compositions – Different Shades of Black

Released in 1995 on “Next School Pioneers”

Different Shades of Black (Shadez) became another early-era P&C group after being connected through Odario, putting out their first release in 1995. On “Next School Pioneers” Shadez is the original lineup of Scuskotch (Len Bowen), Mista Christy (Bigg Casino), and Marvellous, who is Len Bowen’s cousin. Mista Christy’s voice is immediately reminiscent of Boot Camp Clik style New York rap, something that didn’t really exist in Winnipeg at the time. Len Bowen, who wanted to be a rapper in elementary school, is a natural over mcenroe’s boom-bap beats.

Wet Dreams – Twisted Spirits

Released in 1995 on “Wet Dreams”

Twisted Spirits is for the true heads. Originally, Frek Sho and Twisted Spirits were two separate groups within the same clique, before merging under the name Frek Sho. But the original Twisted lineup of Gruf, The Gallivanting Spoof and Mocean (Ismaila Alfa) were a tremendous trio. Over Frek Sho producer Sunil’s beats, Gruf is rapping in the same flow he still uses (now perfected), and Ismaila shows off why he should always be in the conversation for Winnipeg’s best all-time rapper.

Roll Model – Frek Sho

Released in 1995 on “Uncivilized”

Even in 1995 Frek Sho had the most inventive concepts for their songs. Based around some clever wordplay, “Roll Model” is a very creative back and forth duet between Sun Lo (Sunil) and Shazzam (Micill Shazzam Write). The two rapper’s voices complement each other so well that the call and response style only helps to weave together the stories of robbing people (or rolling them). 

Oh – Farm Fresh

Released in 1995 on “Crazy Friction”

Farm Fresh’s second effort, 1995’s “Crazy Friction,” came only 10 months after “The Space EP” yet there’s a huge leap in all aspects, from the beats and the concepts to the quality of production. The standout track on the album is “Oh” which features some of DJ Hunnicutt’s best early scratching and ended up being something of a live hit over the years. 

Braggin’ & Boastin’ – Mood Ruff ft. Mista Christy

Released in 1996 on “Fluid”

Mood Ruff’s second album “Fluid” marked the end of the group’s time with P&C as they moved on and established their own label, Slo Coach. mcenroe delivers a sick beat and Mista Christy lends his impeccable voice and flow to this solid track. 

Patience – Frek Sho

Released in 1996 on “Sho & Tell”

The song that changed it all. The black and white video for “Patience,” with the group out on Winnipeg’s streets in the dead of winter fighting each other for camera time, was the first video from Winnipeg to be played on Much Music. The ensuing 12″ of the song was also the city’s first rap vinyl and marks the merger of Twisted Spirits and Frek Sho into simply Frek Sho. The song itself has many memorable moments, from Ismaila’s Mood Ruff diss, to Gumball’s memorable lines of “Jesus only knew I wore Adidas as a fetus,” to Sunil and Sheldon rapping simultaneous verses. In terms of historical importance for local rap songs, this song is top two and it’s not two.

Comatose – Frek Sho

Released in 1996 on “Sho & Tell”

Although often forgotten in the conversation of Frek Sho, Gumball is an incredibly important part of Winnipeg rap history. The designer of the famous Frek Sho logo and often an early ghostwriter for other group members, Gumball gets his first solo song with “Comatose.” An eerie track based off of a true story in Gumball’s life, “Comatose” shows his rapping skills can equally match his writing skills. 

NFL – Mocean

Released in 1997 on “Mocean”

Following the Wu-Tang playbook, riding a high after “Patience” Frek Sho put out a solo album for Mocean (Ismaila) rather than another crew album. Winnipeg’s first rap CD, “Mocean” is probably the most complete Winnipeg rap album of the ’90s. “NFL” was recorded right before the album was finished and is included as a bonus track, but it has one of the most clever concepts on the album. “NFL” here stands for “No Fakes Live” but Mocean still transfers the football analogy to rap battling. Coupled with a hot beat and some well-placed Method Man samples, this is a banger. 

No Hooks – Mood Ruff

Released in 1998 on the “No Hooks” 12″

Mood Ruff made their first beat on their own and decided to make a video out of it. Shot largely at the Corefest ’97, “No Hooks” is a bass-heavy head-nodder and a fun video to boot. The track also made it onto Mood Ruff’s first 12″ vinyl. The group would quickly follow-up the “No Hooks” video with visuals for “Maintain,” both released on the 1999 album “”

Focus – mcenroe ft. The Gallivanting Spoof

Released in 1998 on “the ethics ep”

The only track with raps by just mcenroe and The Gallivanting Spoof, the two managers/label heads of Peanuts & Corn and Vagrant Hobby (Frek Sho) respectively. Get two rap business guys on a song and they rap about, well, the business of rap. This cut, off of mcenroe’s debut solo effort “the ethics ep,” buried any notions of a lingering Frek Sho and P&C beef stemming from an incident at the Pyramid in September ’95.

Comprehension – Shadez ov Blac

Released in 1998 on “Comprehension”

Fresh off a name change, Shadez ov Blac (Different Shades of Black) joined the growing movement of Winnipeg rap groups self-releasing music videos with “Comprehension.” Submitted to Much Music, the video got into the regular rotation, elevating the group’s status nationally. As early member Marvellous dropped out of the picture, Eclipse (Bad Mannaz) rejoined the group in time to get on the “Comprehension” song and video, while the duo of Mista Christy and Len Bowen continued to hold it down.

The Law – Fermented Reptile

Released in 1999 on “Let’s Just Call You Quits”

Fermented Reptile (Gruf and Pip Skid) were so far ahead of their time, we’re only just catching up twenty years later. “The Law” is an unbelievably brilliant concept song about the violent power of authority and police. Easily the high bar for political rap to come out of Winnipeg, Fermented Reptile helped Peanuts & Corn reach a lot more ears than it might have otherwise. Shout out to the “Glengarry Glen Ross” sample at the beginning.

Thin Line – Fermented Reptile

Released in 1999 on “Let’s Just Call You Quits”

A solo Pip Skid track off the Fermented album, “Thin Line” is a personal favourite. The smartest concept song on this whole list, “Thin Line” takes on the perspective of a conservative, casually racist, suburban-dwelling capitalist. Once you hear Pip’s character lay bare the brutally honest perspective of suburbia’s mindset, you can’t go back to looking at subdivisions the same. When shitty conservative politicians (aka the Brian’s) make shitty decisions you can’t understand, listen to this song and imagine it’s what they’re thinking. 

Music Appreciation – Park-Like Setting

Released in 2000 on “School Day 2, Garbage Day 4”

Park-Like Setting is a post-Farm Fresh DJ Hunnicutt and mcenroe with a young John Smith (Bazooka Joe), before his solo career. The group, along with Fermented Reptile, made up the Break Bread crew, yet another name for the Peanuts & Corn camp. mcenroe claims that when he raps about rap it doesn’t age well, but “Music Appreciation” gives a glimpse at the politics of rap beef in that era.

Blood, Sweat and Tears – Bonafide

Released in 2000 as a video single

Around since 1995, Bonafide finally put out music for the public with the video for “Blood, Sweat and Tears” in 2000. The group would go through many lineup changes over the years but this song features Lazarus on the opening verse, First Born on the second verse, the hook and the beat, and FINI on the third verse. The emotional video and track talks about the loss of close family members and the associated grief and trauma. Bonafide is often forgotten in the conversation of local rap, but they are vitally important to the development of Winnipeg rap.

Uncivilized – Frek Sho

Released in 2000 on “People in Your Neighbourhood”

Frek Sho were the best rap group to come out of Winnipeg. The long-awaited full crew CD, “People in Your Neighbourhood” is a piece of art, almost every song is worthy of being on this list. The concepts are brilliant and original but none more so than the opening track “Uncivilized.” Taking the concept of a posse cut to unmatched heights, seven rappers exchange lines to tell the story of a colonization mission, truly an unrivaled song in the history of Canadian rap. Almost more of a short play set to a rap beat, Frek Sho set the tone early for their opus record.

Life of the Party – Frek Sho

Released in 2000 on “People in Your Neighbourhood”

A personal favourite, this Sunil solo track is really two short songs in one. The first part is a hilarious parody of “Rapper’s Delight” but instead of chicken tasting like wood, it’s really terrible weed. The second part is a light jab at the crossover of R&B and rap in clubs in the late ’90s. The ability to parody songs in such a creative way shows just how brilliant Sunil is not only at beats but at concepts and rhymes. “People” was Sunil’s last project with Frek Sho, he moved to India shortly after and became a massive success under the name Ishq Bector.

Why – Moonshine Kru

Released in 2000 on “Intastella”

What a hot beat. Moonshine Kru were one of the many groups that started coming up in Winnipeg’s rap scene in the late ’90s and early 2000s. Co-produced by a young K-Rup (Rup Monsta), “Why” delivers a track that could still knock right now. Jah D’s, a Frek Sho affiliate who also appears on the “Mocean” album, brings the patois flavour and drops some knowledge.

Great Seasons Hurt – Yy, The Gumshoe Strut & DJ General Gyst

Released in 2000 on “Milch & Allegra”

The first official release from both the Gumshoe Strut and Yy comes on the “Milch & Allegra” album. Indie rap at its finest, “Great Seasons Hurt” has a devastatingly amazing piano/guitar lick that carries the song. Their voices complementing each other, the duet chorus urges the listener to pay closer attention to the nature around us. This album, originally produced with hand-drawn cassette sleeves, also helped spark the second wave of independent releases in Winnipeg rap brought on by Gumshoe’s Your Brother Records. 

The Plants – Gruf

Released in 2001 on “Druidry”

“Ever tried attaching a lie detector to a philodendron?” Who knew you could write a super-hot rap song about the consciousness of plant life? Gruf is a singular rapper not only in Winnipeg but the world, no one else is choosing to rap about these subjects. Gruf really needs to be taught in the schools. Also, big props to mcenroe for hooking up the wild bassline on top of an even wilder beat.

Copsoup – Your Brother in My BackPack 

Released in 2001 on “Factory Seconds”

Your Brother in My BackPack was a supergroup before any of the members had really made a name for themselves. Made up of rappers Yy, John Smith (Bazooka Joe), Satchel Paige (Nestor Wynrush or Ness), and The Gumshoe Strut, “Copsoup” is one of the few officially released YBIMBP songs, making it that much more intriguing. The whole song touches on experiences with police but Ness has the most interesting verse, including a name drop of Amadou Diallo. Feels like it’s time for a reunion record.

Accept or Sin – The Gallivanting Spoof 

Released in 2001 on “Factory Seconds”

Despite being on a P&C compilation, this is the only available solo song from Frek Sho rapper/manager The Gallivanting Spoof. There were plans for an EP that never materialized but this track makes you wish there was more out there. mcenroe’s eerie production and local legend DJ Grasshopper’s elite scratches provide a vibrant backdrop for Spoof to paint a vivid picture of growing up and living in the world of organized Catholicism. 

20 Minute City – Frek Sho

Released in 2002 on “Papercuts”

No other beat on this list hits as hard as “20 Minute City.” DJ Kutdown’s debut song with Frek Sho, the duet between The Gallivanting Spoof and Shazzam has brilliant references, name dropping Richard Dent, the Golden Boy and Mocean. While many solo albums would come in the following years, “Papercuts” is, to date, the last album of new Frek Sho songs. Maybe not the last ever, though.

Indifference – The Gumshoe Strut

Released in 2002 on “Clock/Works”

The Gumshoe Strut’s first solo album “Clock/Works” showed him as a Winnipeg rap triple threat handling the rapping, producing and running of his label, Your Brother Records. Distributed by Peanuts & Corn, Gumshoe stayed on the fringes of the P&C crew while establishing his own strong brand of Prairie hip-hop throughout the 2000s. 

Take as You Will – Yy ft. The Gumshoe Strut

Released in 2003 on “Hold the Fort Down”

Yy’s first solo album “Hold the Fort Down” shows the Portage-la-Prairie rapper already well developed. “Take as You Will,” which features and is produced by The Gumshoe Strut, is a form of hip-hop journalism. Integrating the racist views of people on the streets of Winnipeg, the song explores prejudicial views against Indigenous people by white settlers. The song samples Shazzam on the Fermented Reptile track “Crimes Against Humanity,” connecting it to another important local rap song that touches on similar issues.

L.A.’s Law – dead can’t bounce

Released in 2003 on “I Ain’t Afraid of No Ghost”

The Prairie rap connection is strong. DCB members Ira Lee, Def3 and DJ Kutdown rep Regina, Saskatoon and Thunder Bay but Winnipeg was briefly home for the short-lived Frek Sho-affiliated group. Saskatoon and Winnipeg rap have always had a strong connection and the dead can’t bounce record is seamless melding of the Prairie rap style into one cohesive project. 

Enida Watts – Satchel Paige

Released in 2003 on “Guy, I’m From Here”

What an amazing ode to youthful summertime lovin’. Satchel Paige (Nestor Wynrush) teamed up with The Gumshoe Strut for the now hard-to-find album “Guy, I’m From Here.” Facing legal consequences from the estate of the great Negro League baseball player, the album is no longer available online and remains a hard to find gem. Hit me up if you still need to hear it because this is one of the best Winnipeg hip-hop albums of the early 2000s.

It’s All About – The Gumshoe Strut ft. Grubbs

Released in 2003 on “Let’s Get Dangerous Double EP”

The Gumshoe Strut provided a lot of opportunities for up and coming rappers in the mid-2000s. An early appearance of Grubbs (Rob Crooks) only helps illustrate the fact that the rappers in this era were all connected to each other, and Gumshoe remained a force. 

On A Trip – Dialog

Released in 2003 on “Clinically Depressed”

Dialog was an important member of the Winnipeg hip-hop scene through the ’90s and 2000s. Mostly a DJ, Dialog was also DJ Stress’ partner on the very early rap radio show “The Stress Files.” A long time UMFM DJ, Dialog also had history as a rapper, being a member of the ’90s group Shady Acres, before he released his solo album “Clinically Depressed” in 2003. Despite such a dark album title, “On A Trip” is a jazzy number about a psychedelic mushroom trip. 

Man (Trusted by Millions) – Micill Shazzam Write ft. Gruf

Released in 2004 on “Micill Shazzam Write”

This personal favourite is on repeat. Micill Shazzam Write from Frek Sho released his only solo album in 2004 shortly before leaving Winnipeg for Toronto. The Kutdown produced beat for “Man” has an ethereal chanting sample and a reverb heavy yet sparse bass line over some slapping drums. The Frek Sho rapper commonly known as Shazzam really has two personas: Shazzam, the wild side; and Micill Write, the conscious side. “Man (Trusted by Millions)” is absolutely the Micill Write persona with the striking opening lyrics of, “my blood runs back / to slave ships and great warriors.” Fellow Frek Sho member Gruf stops by to drop some knowledge of his own.

Kinship of the Down and Out – John Smith

Released in 2004 on “Pinky’s Laundromat”

The Winnipeg Anthem. John Smith captures lightning in a bottle with “Kinship of the Down and Out.” Giving a voice to Winnipeg’s North End, Smitty is a rapper of the people and Jason Lapeyre’s video for the song remains an all-time classic. “Pinky’s” was the first time I heard Winnipeg street names shouted out the way Big L shouted out the names of his Harlem streets. “Y’all can sue me / for telling it truly.”

No Time to Quit – Team RezOfficial ft. Wab

Released in 2004 on the original soundtrack to “Stryker”

Originally in Alberta rap group War Party, Team RezOfficial rappers Hellnback and Tomislav collaborated with local rapper Wab for this banger featured on the soundtrack of “Stryker.” 

Expand Horizon – Gruf

Released in 2005 on “Hopeless”

Recorded as an a cappella with the beat then built around Gruf’s voice, “Expand Horizon” is producer mcenroe’s favourite Gruf song. Hard to argue that one. The beat alone defies simple explanation but coupled with Gruf’s methodically melodic vocal cadence, the song becomes transcendent. “Until our eyes and our minds have enshrined the wisdom encompassed in the vastness of the ever-expanding horizon.” Yeah, teach it in schools. 

B-Boy D-Day – Ismaila ft. Shazzam

Released in 2005 on “Mark of the Zebra”

2005 marks the end of an era in Winnipeg, with numerous classic groups calling it a day. None perhaps more devastating than the long-time-coming dissolution of Frek Sho and their label Vagrant Hobby. Ismaila’s “Mark of the Zebra” closes out that chapter with a taste of what would come later in Magnum KI. “B-Boy D-Day” is an old school banger that gives Ismaila and Shazzam a chance to show what they do best.

Withdrawl – Sound Barriers

Released in 2004 on “Sound Barriers”

Gruf has collaborated with a lot of producers. But none of them were also Canadian DMC Champion turntablist DJ Brace. In his first full album as a producer, Brace’s beats give Gruf the room to weave his brilliant narratives. “Withdrawl” is a painfully honest look at consumer capitalism, with Gruf ironically rapping about how great it would be to be rich. The song ends with the beat dropping and Gruf, dripping with sarcasm, chants the phrase “I want money, so much money!” 

Rocketship – Mood Ruff

Released in 2005 on “I Do My Own Stunts”

Mood Ruff’s swansong is likely the most commercial sounding rap song on this list. But if it slaps, it slaps. Ending the twelve-year Mood Ruff run after “I Do My Own Stunts,” Odario went on to form Grand Analog while Spitz reinvented himself as DJ Dow Jones.  

My Ex-Girl – Farm Fresh

Released in 2005 on “Time is Running Out”

Known as a great scratcher and an elite party-rocker, DJ Hunnicutt jumps out from behind the decks for “My Ex Girl,” released on the Farm Fresh reunion record “Time Is Running Out.” A clever play on words, the title actually refers to Hunnicutt’s Red River Ex date. Re-released on a 7″ earlier this year with Hunnicutt’s other rapping song “Betamax,” “My Ex Girl” is a fun ode to summer lovin’. 

Eight Bars Each – Park-Like Setting ft. Birdapres, Gruf, Cadence Weapon, 

Evil, Pip Skid & Satchill Paige.  Released in 2005 on “Craftsmen”

Who doesn’t love a good posse cut? With three rappers (mcenroe, John Smith and the recently joined Yy) already in Park-Like Setting, why not just have six other rappers on for “Eight Bars Each”? Nestor Wynrush, here credited as Satchill Paige, has the best verse. Also, a young Cadence Weapon makes an appearance.

I Ain’t Lazy – John Smith, Pip Skid & Skratch Bastid

Released in 2005 on “Taking Care of Business”

The duo of John Smith and Pip Skid, who had previously collaborated as the Hip-Hop Wieners, connect with a young Skratch Bastid for “Taking Care of Business” and the lead single “I Ain’t Lazy.” A fun video by director Jason Lapeyre shows all the (potential) activities that the trio could get up to. Oh yeah, and Skratch Bastid is a monster on the scratches.

Next Door – Turn the Gun ft. Fermented Reptile

Released in 2005 on “Rap Day”

The Turn the Gun album is a special one, an updated and much darker, grimier “Milch & Allegra.” Yy and Gumshoe Strut are joined by DJ Kutdown on the scratches with Gumshoe producing the whole album. “Next Door” would have already been a glimpse into the underside of Winnipeg urban living but the Fermented Reptile feature and the combined energy of Pip Skid’s anger and Gruf’s bigger-picture-view elevates the song to new heights.

The Art of Murder – Grubbs

Released in 2006 on “Plague City”

After a couple of self-produced bedroom albums, Grubbs (Rob Crooks) put out his debut album on DJ Kutdown’s relatively new Foultone Records. Mostly co-produced by Grubbs and Kutdown (credited as Khela) “Plague City” is an incredibly dark record, with “The Art of Murder” being no exception. 

Get Familiar – Shadez ft. Odario

Released in 2006 on “Every Dollar Counts”

The final Shadez (Shadez ov Blac) group album, “Every Dollar Counts” was ahead of its time. While Len Bowen would continue his rap career, sadly, Bigg Casino would largely retire from rapping following this album, but his strong voice lives on. Odario and Shadez would remain tight through the years, showing up on each other’s tracks consistently. 

Northern Hospitality – Big Bear ft. Wab & Wordsworth

Released in 2006 on “Bear Back”

We got a slapper here. Deep Cave head Big Bear held it down for Winnipeg rap in years when not a lot of other people were and he deserves a lot of respect for that. “Northern Hospitality” is the first time on this list where a local artist brings in a bigger name out of town artist, in this case Wordsworth. Wab also hops on and drops a hot feature on the first verse. 

Love – Bonafide

Released in 2006 on “Chilly City Productions”

All eras of Bonafide are represented on this one song. FINI had begun bringing in new members Fenom, Shomario Gunz and AK, but original member Lazarus still gets a chance to rip it up despite mostly being the groups manager before leaving the group altogether. Without a doubt, Fenom is a singular figure in the history of Winnipeg rap. Self-described as “the Lauryn Hill of Winnipeg,” Fenom is a woman who can rap and sing with equal strength. This era of Bonafide could stand up to any group, though they are sadly under-recorded. Recorded likely in 2003, this song didn’t get released until a few years later.

Game Tight – Bonafide

Released in 2006 on “Chilly City Productions”

Fenom again brings the fire on her verse. Another later era Bonafide member was Shomario Gunz, a name mentioned in hushed tones when brought up in interviews. More than a mysterious figure, Shomario has now completely dropped off the map. But for those years with Bonafide, as the hook for “Game Tight” proves, Shomario was among the best rappers in Winnipeg. FINI (originally from Brooklyn) told me that Memphis Bleek heard a tape of Shomario and insisted on working with him, a collaboration we can sadly only dream about.

Small Town Boys – Grand Analog ft. Len Bowen and Biggs

Released in 2007 on “Calligraffiti”

Coming out of the ashes of Mood Ruff, Odario started Grand Analog, a live instrument, multi-genre group that split time between Winnipeg and Toronto. However, “Small Town Boys” brings that OG energy with a minimal beat and dope features from Len and Biggs from Shadez. Odario, by this point a Toronto resident, always had an interesting perspective on life in Winnipeg. 

Anytime – John Smith

Released in 2007 on “Growing Pains”

A personal favourite from the John Smith catalogue, “Anytime” is the rapper now known as Bazooka Joe just ripping bars. The song comes on the “Growing Pains” album which marks a transition between the heyday of Peanuts & Corn in the early 2000s and the largely inactive years of the 2010s. As McEnroe’s production sound transitioned, John Smith delivers what is probably his most all-around solid record.

Heat – Fresh IE

Released in 2008 on “Lockjaw”

Fresh IE is a Winnipeg rap OG. Long before being a Grammy-nominated Christian rapper, Fresh IE was one of the city’s hottest dancers and up-and-coming rappers. By 2008’s “Lockjaw,” Fresh IE was already well-established as one of Winnipeg’s most successful rappers ever, a vaunted place in which the very humble Fresh IE still finds himself.

Garbage Hill – Nestor Wynrush

Released in 2009 on “Trinnipeg!78”

The rapper formerly known as Satchel Paige settled on the name Nestor Wynrush for the “Trinnipeg!78” album. What’s not to love about a good Winnipeg-centric song? Wynrush is one of Winnipeg hip-hop’s premiere storytellers and certainly the best at weaving in recognizable names and locations into a very personal story. 

Badass Shorty (remix) – Brooklyn ft. Jon-C & Charlie Fettah

Released in 2009 on “Mind of a Heatbag”

A pre-Winnipeg’s Most collab from the Heatbag Records crew, Boogey the Beat produced this club-ready remix for Brooklyn’s first solo album. The eventual Winnipeg’s Most trio show their respective strengths on “Badass Shorty” but Brooklyn’s flow, voice and presence on the mic are what helped make him a super star in Winnipeg rap.

Frankenstein – Rob Crooks

Released in 2009 on “Science is Magical”

Rob Crooks is the best rap government name since Reggie Noble. Previously rapping under Grubbs, Crooks wisely switched to his real name for the concept album “Science is Magical.” Crooks, a notorious battle rapper, pulls no punches and goes all out on “Frankenstein,” with his flow rising to impossibly complex levels. Important to note that Crooks produced this whole project, adding him to the sub-list of rappers/producers represented on the Top 100.

Last Word – Wab Kinew ft. Tinsel Korey

Released in 2009 on “Live by the Drum”

Don’t ever forget that Wab Kinew was one of the most promising hip-hop artists out of Winnipeg in the mid to late 2000s. Off his acclaimed album, “Live by the Drum,” the track “Last Word,” shows that Wab is one of the best storytelling rappers on this list. While his verses are good, it’s the chorus by Tinsel Korey that really elevates the song to the next level. 

On My Own – Nereo II

Released in 2009 on “Foulplay”

Nereo II is an artist with the brush and on the mic. Now primarily known as a mural artist, for a period Nereo was ripping up mics as a Foultone affiliate and member of the group Sleeping Giants. Released on a 2009 Foultone sampler, “On My Own” shows off Nereo’s prowess with the pen. Lyrics addressing solitude and alienation from one’s family hit home the more you listen to this Nas-inspired track.

I Never Knew – Pip Skid

Released in 2010 on “Skid Row”

“Skid Row” is my personal favourite Pip Skid record. Pip’s cement mixer voice and Kutdown’s top notch production make it a highlight of that era. While the obvious song choice off that record would be the lead single “Tens of Dollars,” I enjoy subverting convention. With an interesting, high-budget video and a banging beat, “Tens of Dollars” is a good track but I personally prefer the low-budget Mike Maryniuk video for “I Never Knew.” Pip’s only record on Foultone also begins his collaboration with Rob Crooks, who co-wrote “I Never Knew” and co-executive produced the record with Kutdown.

Eyes on Fire – Magnum KI

Released in 2010 on “Magnum KI”

Foultone was on fire in 2010. Magnum KI combined the talents of Ismaila, DJ Kutdown and Rob Crooks (and later Fenom). Ismaila’s shows off some vocal range on “Eyes on Fire,” going from an incredible rap flow in the verses, to some really strong singing in the hook. There’s a fully completed but never-released Magnum KI album with Fenom in the lineup, a tragedy that none of our ears have heard it. 

Euthanized Herbs – Royal-T & DJ Kutdown

Released in 2010 on “Royal-T & DJ Kutdown”

Oh, did we mention DJ Kutdown is a monster on the beats? Thunder Bay native Royal T (RIP) was most known for his double time flow, which is featured heavily on this Foultone and Deep Cave album. But on “Euthanized Herbs” T raps with a more syncopated flow over an absolute beast of a Kutdown beat. Thunder Bay representing in Winnipeg.

Backroads – Yy

Released in 2010 on “Tape it Back Together”

Not necessarily the most prolific, Yy has quietly and consistently put out some really amazing records throughout his career. 2010’s “Tape It Back Together” is an all-around solid effort with several songs getting the video treatment from mcenroe. But a personal favourite remains “Backroads” a simple but beautiful ode to the gravel veins that connect rural Manitoba. Shouting out small Manitoba towns like New York rappers shout out their blocks, Yy gives Gladstone, Elie and Dauphin their moment of recognition.  

Bikes – Birdapres ft. Pip Skid & Speed Dial 7

Released in 2010 on “Catch An L”

Birdapres, originally from B.C., did have a stint of living in Winnipeg, which includes 2010’s “Catch An L.” Released on Marathon of Dope, this fun track features two of the labels co-founders, Pip Skid and Speed Dial 7, who is from Kortrijk, Belgium. Although initially just a rapper, Birdapres starts producing around this era, making him yet another rapper/producer on this list. 

Winnipeg – Abstract Artform ft. Fashawn

Released in 2010 on “His Story in the Making”

Oh yeah, we’ve got catchy tunes. Another example of a local rapper bringing in an out of town artist for a feature. In this case it’s Abstract Artform (now performing under the name Shea) bringing in Fashawn from California to drop the first verse and chorus on this foot-tapper. 

Gully Is as Gully Does – NWO ft. Jon-C

Released in 2010 on “NWO”

NWO was the Winnipeg supergroup. At the height of both of their efforts, NWO put together the Deep Cave crew and the group Dead *ndians. Over P-Nut’s hardcore beats, the album of posse cuts features nothing but bars. Highlights on this track include Royal-T’s unbelievable flow and Jon-C crushing the feature. 

All That I Know – Winnipeg’s Most

Released in 2011 on “Goodfellaz”

Winnipeg’s Most were a force of nature. “All That I Know” is the most successful single song in the history of Winnipeg rap music, with over 4.5 million YouTube views as the evidence. Stuey Kubrick’s video of Winnipeg’s North End is a gritty, realistic glimpse at the dark side of Winnipeg’s streets which Winnipeg’s Most documented with such accuracy. 

Winnipeg Boy – Winnipeg’s Most

Released in 2011 on “Goodfellaz”

Sampling yourself to make a grimy hardcore beat? Check. Jon-C showing off his rough growl of a voice while rapping about street shit? Check. Brooklyn repping Winnipeg harder than anyone else while changing up his flow seamlessly? Check. Charlie Fettah rapping double time? Check. Don’t mess around with the Winnipeg’s Most catalogue, it’ll fuck you up.

The Sleep – P-Nutty Goldust

Released in 2011 on “Night of the Creeps”

Winnipeg horrorcore at its finest. P-Nut from the group Dead *ndians is a very important rapper/producer in the history of Winnipeg rap. Deep Cave filled so many holes as far as rap subgenres go and P-Nut was behind most of the production.

Make Dollars – Lev

Released in 2011 on “One Hand Washes the Other”

Another Deep Cave rapper with a sick solo album in the early 2010s, Lev brings the Prairie G-Funk vibe with “Make Dollars.” There’s not another album like this one in the Winnipeg rap catalogue.

New Generation – The Happy Unfortunate

Released in 2011 on “No Time to Sleep”

Perhaps best known as the first group of rapper Malcolm-Jay, The Happy Unfortunate held down the underground rap scene in Winnipeg through their many years. A fun, backpack style rap song, it’s hard not to nod along to the chorus of “New Generation.”

Peg City Boi – Brakada

Released in 2011 as a video single

The long running group Brakada, consisting of brothers Mikal and Lahcing, dropped their biggest track with “Peg City Boi” back in 2011. Released right around when the Winnipeg Jets had returned to town, the track is a celebration of living in the 204 and the city’s beloved hockey team. 

I Ain’t a Rapper, I’m a DJ – Pip Skid ft. DJ Bunny

Released in 2012 on “People Are The Worst”

Huge props to Pip Skid for giving DJ Bunny a feature. Winnipeg’s OG of OG’s, DJ Bunny updates a verse he used to rap on the VPW show “Spotlight” which he co-hosted along with Avon T and Mr. Cee. Pip gives respect to Bunny, mentioning that DJ Hunnicutt used to tape “Spotlight” so they could watch it again and again. Pip’s verse here references past moments in his career, including a true story during Fermented Reptile where he and a few others were chased from the Albert by a group of Nazi skinheads. 

They Said – The Lytics ft. Len Bowen

Released in 2012 on “They Told Me”

The Lytics second album, “They Told Me,” is the long-running group’s undisputed opus. Even with hit after hit on the album, “They Said” is an all-time personal favourite. The Lytics main rappers, Ashy (Anthony OKS), Andrew O, and Munga, all drop sick verses. But it’s B-Flat’s production that really defines the Lytics sound. Here it is ethereal and dreamy, a feeling matched perfectly in the song’s video. Often taking a backseat in the rapping department, B-Flat jumps on the track and drops some knowledge, including the quote that opens this entire article. The video version only includes the verses from the group but check the album version of a feature verse by Winnipeg legend Len Bowen from the Shadez. 

Flatline – Young Kidd

Released in 2012 on “From Dreams to Reality”

There are great beats on this list, but none of them is “Flatline.” Now known as YK the Mayor, Young Kidd was the hottest thing out of Winnipeg in the early 2010s and on “Flatline” he shows exactly why, on the versatility of his flow alone.

Cigarettes – Birdapres & Rob Crooks ft. Pip Skid

Released in 2013 on “Argyle”

In an era when underground hip-hop locally began to take a dip, “Argyle” was a highlight. The collaborative project between Rob Crooks and Birdapres, produced by Crooks, is a concept album about high school. This may be the last album that Crooks actually raps on and he raps his ass off. Also, Pip Skid, who was on a lot of features around this time, raps about dropping out of high school (true story).

Tangerine – Bubblz

Released in 2013 as a video single

Heatbag Records co-founder and Hoop Hoprz owner Bubblz doesn’t rap often but when he does, he drops a banger like “Tangerine.” With a heavy West Coast, Bay Area influence, “Tangerine” gives Bubblz a chance to show off his hype G-funk flow.

Buckle Up – Brooklyn ft. Rup Monsta & Zeek Illa

Released in 2013 on “Our Inner Demons”

Produced by Rup Monsta, featuring Rup and Zeek Illa, this late era Brooklyn track is introspective and inspiring. Brooklyn’s raw verse about his struggles with addiction and abusive relationships only hits  harder with his tragic passing only a few years later in 2015. Brooklyn’s music keeps him alive forever but his absence in the Winnipeg hip-hop scene will always be felt. RIP.

Streetz – KiDD Kane ft. Cypha Diaz

Released in 2013 on “New KiDD from Tha Block”

Ever wonder what Three Six Mafia would have sounded like if they grew up in Winnipeg? KiDD KANE, Cypha Diaz and the absolute slapper of “Streetz” have your answer. Extremely heavy and grimy beats, slowed down vocals and a whole lot of drug and violence talk? When history comes knocking, let them know that KiDD KANE invented the sub-genre Dirty North.

Snakes & Ladders – Sleeping Giants

Released in 2014 as a video single

The duo of Nereo II and Illicit never released a full-length album, but Sleeping Giants were a live staple for many years. Thankfully this video exists to capture the boom-bap poetic rap of Sleeping Giants. Illicit now goes by Brendan Grey, the rapper in Super Duty Tough Work, and Nereo II is a successful visual artist and muralist. This would be a fun reunion to see happen.

The Rise in My Descent – Gruf

Released in 2015 on “Surface Area”

The Gumshoe Strut went into a bit of rap retirement, but he returned by producing this entire Gruf album. The beat for “The Rise in My Descent” is the perfect tapestry for Gruf to paint his amazing canvas of words and flow. Nobody raps like Gruf, his style defies explanation and the amount of times he can change up his cadence in a song is unparalleled. Did I mention that Gruf should be taught in schools?

The People’s Champ – A Tribe Called Red ft. Hellnback

Released in 2015 on “Suplex”

While A Tribe Called Red is not a Winnipeg group, the featured rapper on this track, Hellnback has lived in the city for many years. Also, ATCR member 2oolman spent time in Winnipeg over the years. Over the typical, fast ATCR beat, Hellnback matches the song’s energy and represents for his fellow Indigenous people.

Memoirs (Rearview) – Len Bowen ft. Andrew O, Grand Analog & Seun Olagunju

Released in 2016 on “Goin’ Away Party”

Easily the song on this list that I’ve listened to the most, as I look for yet another word of wisdom from the legend Len Bowen. No one can rap in an emotional, elegiac way like Len, especially on this retrospective track about growing up in Central Winnipeg with his mother (“heard what Ma was saying / also what she wasn’t.”) The last verse from Len is particularly poignant, opening with the lines, “You can’t change your life / hardest things to accept.” With Sean Olagunju on the hook and features by Andrew O from the Lytics and Odario from Grand Analog, “Memoirs” also does a call back to another track on this list “Small Town Boys.” 

Sheep – 3Peat

Released in 2016 on “3Peat”

3Peat are an important group in the history of Winnipeg rap because they brought a fresh, younger energy to a scene that had begun to grow stale in the mid-2010s. The self-titled debut album from rappers E.GG, Dill the Giant and BBS Steve has a few strong group tracks, but “Sheep” is a personal favourite because of the message of anti-trend following. Another rapper/producer (and DJ) is added to the list here with BBS Steve, who continues to make his name as one of the best producers in the city. 

Game of Dice – E.GG

Released in 2016 on “Alverstone”

Coming hot on the heels of the 3Peat group album, E.GG drops the first solo project from the 3Peat/4th Quarter Records camp. “Alverstone,” named after E.GG’s childhood West End street, is a personal portrait of life growing up in an immigrant household on a rough side of town. Produced by underground stalwart Crabskull, “Game of Dice” is evidence that E.GG is in the top tier of lyrical rappers to come out of Winnipeg. His soft-spoken but don’t-fuck-with-me mentality gives E.GG the feeling of a Winnipeg Nas.

Mind Spinnin’ – Cypha Diaz

Released in 2016 as a video single

Cypha Diaz (formerly Lu Cypha) is an underrated local rapper, coming out of Moonshine Kru and continuing a working relationship with Rup Monsta while still making his own name. “Mind Spinnin'” partners Cypha’s hardcore rap energy with the solid production and scratching of DJ Kutdown, who here samples the later “Star Wars” films for some added flavour. 

Bake & Shark – Nestor Wynrush ft. Birdapres, Bad Mannaz, Len Bowen, Yy & DJ Brace

Released in 2017 as a single

An all-star track. Hard to say who has the best verse here, honestly. Competition makes good rappers even better evidently. Having World DMC Online Champion DJ Brace on the cuts makes it extra funky. Coming as part of a run of singles released by Nestor Wynrush through the mid-2010s, “Bake & Shark” proves the older guys can still bring it. 

Emails – Dill the Giant ft. Ari IQ

Released in 2017 as a video single

Another 3Peat solo track, Dill the Giant masters the chill yet street vibe on “Emails,” with rapper Ari IQ dropping a sick feature. BBS Steve shows his versatility behind the producing decks with this slower, spacier beat. 

Unforgiven – Malcolm-Jay ft. CJ the Grey

Released in 2017 on “The Enemy Within”

Malcolm-Jay has quietly been one of the most prolific rap artists out of Winnipeg in the last decade. Producing as well as rapping, Malcolm-Jay also works hard to include less-heard and up and coming voices in the local scene. On “Unforgiven” the raw talent of young CJ the Grey is featured alongside Malcolm’s double time flow. 

Lights – HAVS ft. LOA

Released in 2018 on “Distortion”

Definitely in the new school of hip-hop and heavily infused with R&B vibes, HAVS drops a banger with “Lights,” a track about shitty relationships. Saskatchewan/Winnipeg artist LOA drops in for a dope second verse.

Resurrection – Charlie Fettah & Crabskull

Released in 2018 on “Fettuccine Pharaoh”

Charlie Fettah returned after several years of laying low with “The Fettuccine Pharaoh,” a collab project with producer Crabskull. Over Crab’s eerie and ominous beats, Fettah raps a raw picture about his past, his ‘comeback’ and why it’s important for him to keep making music. “I got demons in my rearview / I ain’t letting ’em in.” 

Phasez – FC Coconut ft. E.GG

Released in 2018 on “Slopoke”

Originally from Istanbul, FC Coconut has been a staple in the underground Winnipeg hip-hop community for a few years. 2018’s “Slopoke” is mostly a beat tape but also features some Winnipeg’s best rappers, including E.GG who consistently has some of the best lyrics to ever come out of Winnipeg.

Hold On – The Lytics

Released in 2018 on “Float On”

The Lytics just keep doing what they’re best at: dropping feel-good bangers that make you think. Perfecting their sound over so many years has led to the group’s voices meshing in a way that only helps to complement the positive vibes of their music. B-Flat’s production again takes the driver’s seat but the opening verses by Ashy (Anthony OKS) and Munga set the pace for the rest of the track. 

GWAP – 3Peat ft. 2oolman

Released in 2018 as a video single

A Tribe Called Red producer 2oolman teamed up with young legends 3Peat for this high-energy head-nodder. BBS Steve rocks the hook and lets us know that he likes his sneakers scuffed. Dill the Giant goes hard, slowly speeding up his flow throughout his verse. E.GG brings a solid verse about the rap hustle life. The trio each bring their hottest cadence and show that lyrics aren’t dead in modern hip-hop. Later released on “3Peat 2” in 2019.

FTP – Super Duty Tough Work

Released in 2019 on “Studies in Grey”

Fuck ’em. “But it’s not just the cops / it’s trickle down corruption, this shit is rotten from the top.” Super Duty Tough Work was nominated for a Polaris Prize for “Studies in Grey” which means that self-important rich-ass music industry people in Toronto had to listen to this song at least once. A moral victory.

Optimist – Sir Louie ft. Khalil

Released in 2019 as a video single

Sir Louie is a second-generation Winnipeg hip-hop artist up on the come up. At the forefront of a clique of promising young artists, including featured rapper Khalil, Sir Louie and the 4eighn World camp are certainly names to watch for in the 2020s.  

Prayers for My Dawgs – Myazwe

Released in 2019 on “Things I Never Said”

Winnipeg’s most successful new rap artist, Myazwe is from the South Side of Winnipeg and reps it harder than anyone else ever has. Listening to Myazwe, you really think that there is no ceiling, he can go as far as he wants with such a strong work ethic. “Prayers for My Dawgs” is an introspective track but it remains a personal favourite. “Can’t even imagine coming in second place,” is Myazwe in a sentence.  

Nobody Loyal – YSN Fab

Released in 2019 on “Made 4 More”

YSN Fab is giving everybody a run for their money. The young South Side Winnipeg rapper is gaining quite a following, but it all started with “Nobody Loyal” in Pascal Beatz’s basement in St. Vital. While Fab works with many producers, his best work is with Pascal and nothing touches this first track that they recorded together. Definitely expect to hear the name YSN Fab again. 

Never Back Down – Kairo & Hoopaloop

Released in 2019 as a single

Kairo doesn’t necessarily get enough attention as he deserves but he is one of Winnipeg’s best underground rappers. Frequently addressing issues of issues of racism and police brutality in his music, “Never Back Down” touches on some of the darker sides of living in Winnipeg over a hard-slapping Hoopaloop beat. 

Not A Terrorist – The OB

Released in 2019 on “Never Ever Ville”

Coming out of the Studio 393 rap programs, The OB is continuing the very long and very proud Winnipeg tradition of making weird rap music that doesn’t sound like anybody else. Producing and rapping, The OB comes with an important track, split into three separate parts, that deals with the personal effects of racism and The OB’s interactions with cops. 

42 – Nestor Wynrush

Released in 2020 on “Roxbury & Wooden Legs”

A project a long time in the making, we are all richer for having heard “Roxbury and Wooden Legs.” Connecting Jackie Robinson and Terry Fox through the number 42 (Robinson’s jersey number and the number of kilometres Fox ran in a day), Nestor Wynrush tells his own story about being both Black and an amputee in a way that can connect with anyone who listens. “Don’t you put me in a box / label me on what I’m not / I’m almost out of control / I’m trying to keep control.” 

Dutty Forces – Mooki

Released in 2020 on “Mooki Tape”

Mooki is bringing a much-needed new energy to the current rap scene. A member of the 4th Quarter Records family with 3Peat, Charlie Fettah and Ed Riley, Mooki collab-ed with BBS Steve for “Mooki Tape.” Like so many before him, Mooki originally comes from the breakdancing world but on “Dutty Forces,” he tells a personal story in a subdued voice, the kind that makes you lean in to hear it better.

Author’s Note/Corrections:
-J-Style plays all instruments and does all vocals on “Main Street”
-Turn the Gun was not produced entirely by The Gumshoe Strut, the album features production from mcenroe.
-“All That I Know” was released in 2010 on the album “Winnipeg’s Most”

3 Replies to “Winnipeg State of Mind – Top 100 Winnipeg Hip-Hop Songs”

  1. Author’s Note/Corrections:
    -J-Style plays all instruments and does all vocals on “Main Street”
    -Turn the Gun was not produced entirely by The Gumshoe Strut, the album features production from mcenroe.
    -“All That I Know” was released in 2010 on the album “Winnipeg’s Most”

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