Kenny's become a main attraction on his own, but the year he came to life in "Dennehy" Kenny was part of a cast of characters milling about in Serengeti's mind. Even back then Serengeti had such a strong idea for Kenny that Ben Westhoff kicked off his Chicago Reader profile of the then-up-and-coming rapper by describing the character in its zygote state:
"Kenny," a northwest-sider with a mustache as big as Mike Ditka's forehead, likes to lounge around the house in Zubaz pants and owns all of Brian Dennehy's and Tom Berenger's movies on laser disc. When he's not playing softball with the guys he's cruising around town looking for a decent Pontiac Fiero with a for sale sign.
Serengeti teased out Kenny's story on 2009's Conversations With Kenny/Legacy Of Lee, but his dedication to the character really came to a head with the release of There's a Situation on the Homefront in 2010; it's billed as an unreleased album from an early 90s hip-hop group Kenny rapped in called Tha Grimm Teachaz, which broke up after opening for Shaq at a show in Philly. There's a Situation on the Homefront is impressive, as not only do Serengeti and company absolutely nail early 90s rap styles but 'geti really shows his dedication to filling out Kenny's. The Bandcamp page for the album even includes a biography of Tha Grimm Teachaz that details what happened to Homefront and another unreleased album called Da End iz Near: "Fortunately, both albums were unearthed in 2010 by Kenny's little brother Tanya Dennis, while cleaning out his garage."
Last year's Kenny Dennis EP builds on Tha Grimm Teachaz storyline with a track called "Shazam." It's a diss track aimed at Shaq, who became Kenny's nemesis at Tha Grimm Teachaz final show; when I spoke with Serengeti about the EP last year he told me that Kenny's beef with Shaq started after the dude caught Shaq making fun of his mustache, and Kenny still gets enraged anytime someone mentions the basketball star and onetime rapper. Shaq pops up at the end of the Kenny Dennis LP when Anders Holm (of Comedy Central's Workaholics) talks about Kenny's disastrous 50th birthday celebration, which abruptly ended after a friend of Anders's showed up in a Shaq jersey.
That's a small fraction of Kenny Dennis's absurd and elaborate narrative, and it's just part of what makes Serengeti's growing backlog of Kenny-related material so endearing. Much of Kenny's enduring appeal is in the details, and the Kenny Dennis LP not only adds more color to Kenny's already colorful existence but also pushes Kenny's world further into our own. The contributions from Anders Holm are key, as his skits not only litter Kenny's narrative with more detail but also give the unusual and magnetic character some dimension that Serengeti couldn't quite manage on his own.
Anders talks about his relationship with Kenny as a natural part of growing up—Kenny's the guy who played softball with his dad and got Anders backstage at the Riv during a Grimm Teachaz show (aka "GT Show '93"). Anders actually grew up in Evanston, which gives Kenny a newfound tangibility as Anders's anecdotes about, say, driving to Indiana to buy illegal fireworks place Kenny firmly in this universe when for years he'd largely remained a fixture in a world of Serengeti's creation. Anders's real-world connection to the Chicagoland area is a subtle detail, but one that displays Serengeti's dedication to his alter ego and a strong desire to get listeners to form a real bond with a fabricated rapper.