K Kirkland On Kevin Hart, Jay-Z, DMX, Elon Musk, Tupac, Biggie, Cam Newton, Performance by Awich

In Part one of this episode of Club Shay Shay, Shannon Sharpe sits down with the incomparable TK Kirkland—a trailblazing stand-up comedian, cultural critic, and one of the most seasoned voices in entertainment.

With over 40 years in the game, TK has shared the stage with legends, rocked sold-out crowds around the world, and built a reputation as comedy’s best-kept secret. Known for his raw storytelling, street-smart wisdom, and undeniable presence, TK is a veteran who’s seen it all—and lived to tell the wildest stories you’ve never heard.

The episode kicks off with an electric performance from Japanese rap star Awich before Shannon dives into a dynamic conversation with TK Kirkland. TK opens up about getting his start opening for N.W.A. and New Edition, and what it was like working with hip-hop heavyweights like Jay-Z, Lloyd, Gwen Stefani, Birdman, Lil Wayne, Eminem, Missy Elliott, DMX, Nelly, Eve, and Timbaland.

TK reflects on the time MC Ren slept with a woman he brought on tour, his take on whether Jay-Z owes Dame Dash, and why he believes Elon Musk should be quiet. He shares advice from Andre 3000 on co-parenting, his love for DMX—who he calls the greatest solo rapper of all time—and the eerie experience of being with Tupac the day he was shot and Biggie on the day he died.

He opens up about his time behind bars, including sharing a cell with Rick James, the Menendez brothers, and Tupac. He recalls being booed while performing in jail, and talks about working with Mike Epps, Sandra Bullock, and Godfrey. He shares his firsthand experiences with Suge Knight, R. Kelly, and Diddy, and even admits to robbing Charlie Murphy’s Rolex and stealing from Diddy. He also shares memories of knowing Richard Pryor, Keenen Wayans, and Prince before they made it big.

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