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In a recent installment of the Club Shay Shay podcast, standup comedian TK Kirkland recalled hiring rapper Jay-Z to perform for his 35th birthday party. In the July 2, 2025, episode, Kirkland said that the rapper arrived late to his party, which made him not want to let the performer go on stage. However, he said his crew eventually convinced him to let the Roc Nation founder perform, and he ended up being impressed.
"I hired him first for my birthday party, [my] 35th birthday party. He came, he was late. I didn't want him to go on," TK mentioned.
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TK admitted that his frustration with the rapper stemmed from his own "egotistical" nature. He added that his relationship with the Grammy winner strengthened after the latter gained success and took him on the Hard Knock Life Tour.
"So we rocking the Hard Knock Life Tour, and that's how I met with Cash Money, and it was just a great moment."
TK Kirkland reflects on Jay-Z's loyalty to his crew
Elsewhere in the Club Shay Shay podcast, host Shannon Sharpe asked TK Kirkland if he noticed the Song Cry rapper's entrepreneurial side when he was still focused on music.
"Although he got his start in music, he doesn't do a whole lot of music now. Maybe he'll jump on somebody's feature, but for the most part, Jay-Z is a businessman outside of the world of music. When you was with him, did you see this entrepreneurial side of Hov then?" Shannon Sharpe questioned.
In response, Kirkland emphasized Jay-Z's loyalty towards his team. Citing the rapper's example, the comedian explained that when one takes care of their team, they are ultimately blessed in return.
"The thing about Jay-Z, and I always noticed this in life, when you take care of your crew, you get blessed, right? When Jay-Z turns the corner in the Bentley, his crew turns the corner in a Bentley."
TK recalled a story from a show in Philadelphia when Jay-Z and his crew arrived in about nine different-colored Bentleys, showcasing the 55-year-old rapper's commitment to his team.
"I ain't never seen these colors in Bentley's before. Now I got a little jewelry on. But when they hit the stage, it lit up the stadium, right? Like when the lights hit it. It was ice like that. It lit up the stadium. It was a different type of rainbow type blue, purple, pink. I still remember to this day cuz I was there. So that's what I liked about [him]."
TK further shared a personal story of the day rapper Tupac Shakur was shot. He recalled being with Tupac and Mike Tyson in Las Vegas on the day of the shooting. After Tyson's fight, they were headed to a party hosted by Suge Knight at Club 66, Kirkland stated.
However, TK explained that he had taken fat-burning pills that day, which he didn't know should not be combined with alcohol. He consumed alcohol later that afternoon, due to which he felt unwell and stayed in his hotel room. While watching the news on TV, he heard that Tupac, who was 25 years old at that time, had been shot.
The full conversation between Shannon Sharpe and TK Kirkland is available on Shannon's official YouTube channel.
