A Guide To Big Sean’s Massive Detroit Showcase “Friday Night Cypher”


DETROIT, MI – JUNE 29: Detroit native and American rapper Big Sean, real name Sean Anderson, throws the ceremonial first pitch prior to the game between the Detroit Tigers and the Kansas City Royals at Comerica Park on June 29, 2017 in Detroit, Michigan. The Tigers defeated the Royals 7-3. (Photo by Mark Cunningham/MLB Photos via Getty Images)

A Guide To Big Sean’s Massive Detroit Showcase “Friday Night Cypher”


DETROIT, MI – JUNE 29: Detroit native and American rapper Big Sean, real name Sean Anderson, throws the ceremonial first pitch prior to the game between the Detroit Tigers and the Kansas City Royals at Comerica Park on June 29, 2017 in Detroit, Michigan. The Tigers defeated the Royals 7-3. (Photo by Mark Cunningham/MLB Photos via Getty Images)

It’s not really worthwhile to talk about whether Big Sean’s new album Detroit 2 is any good. Honestly, you probably don’t care. It’s a Big Sean album, right? If you are predisposed to liking a Big Sean album, you will probably like it. If you think Big Sean is an irredeemable cornball, you will find plenty of evidence to support your hypothesis. Detroit 2 is certainly a successful Big Sean album — vast, sprawling, jammed with famous people, sometimes quite engaging, occasionally even exciting. Sean has grown more relaxed and confident as a rapper over the years, though he still comes up with lines so dumb and embarrassing that I want to bury myself in sand when I hear them. (My favorite one this time: “I’m about to delete my Twitter and follow my intuition.”)

But the real centerpiece of Detroit 2, at least as far as my particular strain of rap dorkism is concerned, comes late in the album. That moment arrives after the potential singles and the Erykah Badu slam poetry and the sample of Michael Jackson’s “Human Nature” and the song where Sean and No ID flip the same bit of the Akira Ifukube Godzilla score that Pharaohe Monch already flipped on “Simon Says.” That moment lasts nearly 10 minutes. It’s the grand, ridiculous all-Detroit posse cut “Friday Night Cypher,” a massive and ungainly and glued-together monster of a song that features 11 different rappers from the same city.

“Friday Night Cypher” is kind of an ugly experiment of a song, and it doesn’t really hold together. Plenty of the rappers featured don’t even sound comfortable on it. I love it anyway. It’s just fun to think about. Big Sean is the only person who could’ve pulled this off — a Detroit-born rap star who never sounded much like a Detroit rapper but who clearly pays serious attention to what’s happening in his hometown. Detroit has the greatest underground rap scene in the world, and I honestly have no idea how many of the city’s rap stars are even paying attention to the roiling world of loud and flamboyant Detroit hard-heads currently cranking out music on YouTube. But Sean knows, so Sean fucked around and put Sada Baby and Boldy James and Eminem on on the same song. It doesn’t even matter that those three rappers have no business together, that they have nothing musically in common other than being rappers from Detroit. Sean still made it happen.

If “Friday Night Cypher” is a sort of beginners’ guide to the world of Detroit rap, then we should treat it as a roadmap, a chance to get deeper. So now let’s give the talking points on every single person on “Friday Night Cypher” — every single you should care. (We’re going in the order that all these rappers appear on the song.)

Tee Grizzley

Meek Mill-esque young street-rap fundamentalist. Correctly identifies Clipse sample. Did a year and a half in prison for robbery, then came home and released “First Day Out,” the hard, muscular 2016 track that made him famous. Still probably best-known for the Instagram of LeBron James lifting weights and making angry faces while listening to “First Day Out,” and for the video of Steph Curry making fun of the LeBron faces at a wedding. Grizzley is part of the 300 empire, and he hasn’t yet lived up to the early promise of his My Moment mixtape, but he can definitely rap.

Best line: “Fresher than you, fuck you and your stylist/ Paid 90 for my grill, then lost it — that’s why I ain’t smiling.”

Kash Doll

Only woman on “Friday Night Cypher.” Ex-stripper currently working the lucrative “sneery tough pretty girl who will take all your money and leave you with pulsating hearts for eyes” lane. Tons of charisma. Could be a star in the making. Doesn’t really seem like a product of the Detroit underground even though she has that real head-slap energy. Has already outrapped Big Sean a couple of times. Arguably stole “Sociopath” away from Pusha T.

Best line: “Bitch, I’m at my pinnacle/ I used to shop at Pinnacle/ Your n***a still drink Pinnacle/ Bitch, your taste is pitiful.”

Cash Kidd

A regional underground staple who’s been at it for a minute. A living testament to how much you can get done with a little bit of confidence and great slurry-nasal-yammer Detroit accent. Not one of the best rappers in Detroit, but that’s only because Detroit is an embarrassment of riches. A solid prospect who may be here because it’s fun to have two rappers named “Cash” in quick succession.

Best line: “I keep dying in my dreams, but life’s great when I stay woke/ Bet you love dreaming, that’s the only time you ain’t broke.”

Payroll Giovanni

The veteran. A scene elder who helped lay the groundwork for this particular moment. Became a Detroit big dog in the mid-’00s as a member of the thriving Midwestern crew Doughboyz Cashout. Remained a big dog by projecting effortless authority while sounding disgusted by everyone he comes across. Made a series of records with producer Cardo that sound like they’re stuck in a glorious ’90s West Coast dream. Never misses.

Best line: “Rap failed, oh well/ Give me back my scale and a burn-out cell/ I’ll grow clientele.”

42 Dugg

Detroit’s newest star. Teamed up with Lil Baby to release one of 2020’s biggest anthems. Would have to stand on his tiptoes to see over the roof of a Honda Civic. Knows his way around a hook. Raps like he’s fighting off a severe lung infection. Whistles at the beginning of every song, which shouldn’t work but does. Spent the summer on the run from authorities even as he had multiple songs on the Hot 100. Facing a possible years-long prison sentence but still just came out with a song with Marshmello. A great rapper.

Best line: “I ain’t signed a deal yet/ Fuck it, I don’t need ‘em.”

Boldy James

A master at work. Raps about crime-life heartbreaks and travails with a writerly eye and a heavy sense of gravitas. Sounded like he was 65 years old even when he first showed up, more than a decade ago. Spent years in the underground-rap trenches before going on a stunning creative roll. Thus far in 2020, released two full-length masterpieces, then signed to Griselda and came out with another truly solid record. Doesn’t make much sense in the context of a crowded track like this one, but can tear your soul to pieces if he gets room to operate.

Best line: “Workers begging me for time off, asking me for raises/ Took me six hours to count it, bubble wrap it up, and tape it.”


Always in the mix. One half of the triumphant duo Drego & Beno. (It’s weird that Drego is on the song but Beno isn’t.) Always sounds like he’s having fun even when he’s talking blood-curdling shit. Usually comes off effortless, even if he’s consistently operating in the upper ranks of a hugely competitive Detroit world. Only gets like 20 seconds on this song — on a weird boom-bap beat-sliver that doesn’t suit him at all — but it’s cool that he’s here.

Best line: “We was standing on the block, thugging with the serpents/ Get caught with Kurtis Blow on me, and they gon’ close the curtains.”

Big Sean

Built a house on that ass. That’s an ass-state.

Best line: “Million-dollar calls, you can’t merge in/ Based God, how I got my curse lift.”

Sada Baby

The big bad wolf of this shit. A hungry, freaky ripper who puts out great songs more often that some of us do laundry. An overwhelming presence who can rap like a demon and still come up with at least one genuinely hilarious line per song. Currently on a hot streak that has lasted at least two years. Might never be a mainstream star, but could easily remain a regional god for as long as he draws breath. Should’ve been given way, way more bars on this one.

Best line: “Every clip we got extended/Yellow perkys look like Minions/ Put Church’s Chicken on your n***as, scrape them boys for half a biscuit.”

Royce Da 5’9″

Ultra-solid Detroit pillar with a handful of classic moments who owes a whole lot of his longevity to an Eminem association that goes back to “Bad Meets Evil.” Made the baffling decision decades ago that his utterly average height should be a part of his rap name. A strong rapper who has always come off as a bit of a hotep. Spends a lot of his verse fuming about the perceived racism of cancel culture. Takes up a spot that should’ve maybe gone to Elzhi. Still, every city should have a veteran this solid.

Best line: “I thought I told you motherfuckers I ain’t need a budget/ I ride with them guys that society begrudges.”


The most popular rapper of all time. Will always be considered an etched-in-stone legend even if he continues to crank out neener-neener word games for 50 more years. Has probably read every bad review he ever got, and will never stop raging out about any of them. (Who can relate?) Sounds like he’s mostly having fun here.

Best line: “Bitch, if you pull up with a stick, it’s a car with a manual transmission.”


1. Ramirez – “Children Of The Void” (Feat. SolMula)
Anytime a bass tone makes me feel like I got kicked in the balls, I know I’m hearing something special.

2. Frisco – “Red Card” (Feat. Skepta, Jammer, JME, & Shorty)
I like this because it’s the members of Boy Better Know, a dominant grime crew, just all going in together, everyone trying to outdo everyone else. But I’ll be honest here: I also like this because of Skepta’s ICP shirt.

3. Rucci & ALLBLACK – “Okay Doeee”
It’s been almost 20 years since that initial hyphy explosion, and that sense of hard choppiness still pervades California rap music. I love it.

4. Shawny Binladen & Bizzy Banks – “Workhardt”
Shawny Binladen is from Queens, not Brooklyn, but this track still finds Brooklyn drill in an intriguing place. Those berserk off-kilter drum patterns, it turns out, mesh beautifully with that old New York sense of cinematic grandeur.

5. 30 Deep Grimeyy – “Toy Story”
There’s a snake in my boot.


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