If you’re unfamiliar with the saga of Serengeti’s beloved Bears-worshipping character Kenny Dennis, Kenny is a cross between Ron Swanson, a Bill Swerski superfan, and the best Golden Age rapper that you never heard. The more nuanced truth is that the KDz is totally singular.
Kenny Dennis is the most whimsical, hilarious, and strangely poignant fictional character in hip-hop history—a true blue collar hero of modernity: a mustachioed Chicagoan who raps in a flat Midwestern bluster. When he debuted on 2006’s Dennehy, Kenny was a playful near-stereotype, the hip-hop Chicago Party Aunt. In the ensuing years, Serengeti developed the character across multiple albums and EPs. Kenny drinks O’Doul’s for the taste. The mustache is a tribute to the only photo he ever saw of his father, wearing a fake mustache on Halloween.
The saga follows the life of Kenny Dennis through his career as part of the old school rap group Tha Grimm Teachaz, to his middle age, the revival of his rap career with the hip-house duo Perfecto, and his relationship with his wife Jueles, who has a music career of her own. While the saga is sprawling and spans over a dozen albums, there is no official chronology or “Kenny Dennis Cheat Sheet” so we tried our best to provide one.
1. Serengeti – Dennehy (2006)
We are introduced to Kenny Dennis, the life of Serengeti’s alter ego, a middle-aged man living with his wife, Jueles, in Chicago. Kenny enjoys grilling chops and brats with his buddies while drinking his favorite brew, O’Doul’s.
He also enjoys playing softball in the park and has a passion for the professional sports teams of Chicago. His favorite actors are Brian Dennehy and Tom Berenger. You can see him driving his damn Buick.
2. Serengeti – Conversations with Kenny/Legacy of Lee (2009)
This time Kenny has Jueles problems and his life hits a new low, so he starts going to hip-hop shows and abusing Bud Light. Serengeti also introduces a new character, Lee, who’s life is ruined when thugs starts selling crack from his laundromat. Both Kenny and Lee decide to make rap demo tapes.
3. Tha Grimm Teachaz – There’s A Situation on the Homefront (2011)
The origin story of Kenny Dennis. While cleaning his older brother’s garage, Kenny’s younger brother, Tanya, finds a cassette labeled “TASOTH.” The cassette, as it turns out, is Kenny’s old rap group Tha Grimm Teachaz’s lost Jive Records debut, There’s A Situation On The Homefront.
As the story goes on, the group’s path to success went awry at the ‘92 Jive Records Showcase in Philadelphia, where Tha Teachaz were opening for Shaq, rap group the Fu-Schnickens, and R&B singer Tevin Campbell. Shaq insults Dennis’s mustache. The group implodes and Dennis is inconsolable. Jive drops the group from its label and the Teachaz album is shelved. Dennis returns to Chicago, works the beer trucks, and plays adult league softball on the weekends.
4. Serengeti – Kenny Dennis and Perculators (2012)
Also confusingly known as “Kenny Dennis EP” This is more of a diss-record by Kenny against Shaq. You could find the idea of Kenny Dennis recording a diss song against Shaquille O’Neal funny in the abstract, but “Shazam” works a lot better if you understand that it’s retaliation for when Shaq mocked Kenny’s mustache at the 1993 Jive Records Showcase back when Shaq was rocking with the Fu-Schnickens.
5. Serengeti – Kenny Dennis LP (2013)
Kenny Dennis LP is narrated by Anders Holm, who Kenny affectionately calls “Ders” and the album relays the events leading up to Kenny’s 50th birthday celebration at a Ruth’s Chris Steakhouse in Los Angeles.
Early in the album, Kenny and Ders meet at Sharper Image on Michigan Avenue in Christmas 1988, when Dennis used his store credit to buy Ders a shower radio. The album-closing party is chock-full of Kenny’s celebrity friends-among them, several American Gladiators and actor Michael Dudikoff. The only person who wasn’t at Kenny’s birthday party was Kenny Dennis himself.
6. Serengeti – Kenny Dennis III (2014)
The story this time around has Kenny hooking up with his friend Ders (Anders Holm) to tour malls with a ’90s high-energy hip-house group called Perfecto, the flailing has-been grinding through the most depressing tour imaginable while refusing to acknowledge that he isn’t a superstar.
Kenny’s also battling a twenty-year pill addiction, egged on by his new friend Joji. He’d sobered up around the Bulls’ first championship in ‘91, but on Kenny Dennis III he relapses-enabled by the deviant Joji. The record is haunted by neurosis, paranoia, and disillusionment.
7. Perfecto – You Can’t Run From the Rhythm (2015)
In the Kenny Dennis Saga, Perfecto is a fictional band consisting of Kenny and Ders, who were securing mall gigs throughout the Midwest, leading up to a climactic talent show at the Mall of America.
But just before the gig, Ders’ agent scores him an audition in L.A., playing Mr. Drummond in a reboot of Diff’rent Strokes. He abandons Kenny just hours before the Mall of America gig.
Perfecto also tells its own origin story. The 17-minute long, “The Labrador” is essentially the novel-as-song—explaining how Rafal got into production after spending nearly nine years writing a 9,000-page plus book at his day job. There was a lawsuit. There were illegal confiscations. But everything eventually worked out after Rafal discovered a computer program that taught him how to make beats.
8. Jueles – Butterflies (2018)
Butterflies is actually an R&B record by Kenny’s wife, Jueles. It’s 1992 again and Jueles has her own dreams of fame. Here, Kenny Dennis is a supporting character, relegated to erratic appearances in phone call interludes between sleek, bouncy ‘90s dance production.
In Jueles’ debut album, she tells their story through her eyes and though her songs. She sings about her big dreams and musical aspirations, her infatuation with Tom Selleck, and their meeting that tips off a series of fateful events.
Butterflies provides a missing piece to the Kenny Dennis story, illuminating a tragedy that feeds his manic state and leads to his eventual meltdown.
9. Serengeti – Dennis 6e (2018)
The saga’s (seeming) conclusion. Kenny Dennis is alone in an apartment, finally facing the mustache in the mirror.
Gone is the good-natured humor. The tough guy bravado directed at fake MCs is revealed to be a cover for a mental break that left him stuck in the ’90s-hence Perfecto’s obsession with Shaq and C+C Music Factory-esque beats.
On Dennis 6e, Kenny is stripped bare, reflecting on the past three decades of his life. (We learn Jueles likely died in plane crash in 1993 and that Kenny has a psychotic break and moves to Minnesota and shaves his mustache.)
10. Serengeti & Kenny Segal – AJAI (2020)
Ajai is the name of the co-main character, who is a HUGE sneakerphile. Ajai’s obsession with both shoes and collabs ultimately unravels his life. “He’s just a fella who loves his wife totally, but he’s hooked on shopping.”
Ajai’s story comes together with that of Kenny Dennis as the characters themselves intertwine. One of Ajai’s pair of shoes gets accidentally drop-shipped to Kenny Dennis. He happened to need some shoes too, cause his Brooks were devastatingly messed up, they had no traction or anything.
So Kenny puts them on, and walks outside, just going to the store, when he’s approached by another person, who asks to buy those shoes for $4,000 cash. Kenny sells the shoes and that’s how he got his whole introduction to the hypebeast world.
11. Serengeti – KDxMPC (2020)
KDxMPC is presented as the final(?) entry in the Ajai Saga. Ajai is living in Minneapolis with Kenny Dennis now, and the kid’s wrapped up in a similar set of delusions – that “the wife’s coming back any-day.”
Meanwhile Kenny keeps busy, adding onto his drop-obsession, other topics including: women’s feet, the availability of comfort food, complications with neighbors, selling custom burger smashers, and taking a shower, taking a shave, taking a walk…
12. Serengeti – AJAI II (2023)
The sequel to Ajai, which continues the story of Kenny Dennis and sneakerholic Ajai. Ajai’s shoes have now led him to a new happier life now that Ajai got a job at Lord & Taylors, selling suits. The album ends on a bitter note though as Ajai has his apartment robbed and all his drops copped.
13. Serengeti – KDIV (2024)
KDIV is the next installment in the Kenny Dennis Saga. Ders comes to visit. Ajai is not well living in 6E. Kenny is doing well with his new girl Elaine but it’s revealed that Jueles is BACK??
Jueles apparently never got on that plane in 1993 that ultimately crashed and used it as a sign to keep quietly living her life, only to reveal herself to Kenny thirty years later.