Sheryl Underwood says Tony Hinchcliffe warned her he would joke about her husband's suicide at Kevin Hart Roast
"Tony Hinchcliffe walks up to me. He said, I'm Tony Hinchcliffe. I said, I know. And I said, how you coming? He said, I'm coming, your husband suicide and you being raped. And I said— he said, well, what are you thinking? I said, it better be funny."
About this episode
Comedian Sheryl Underwood joins the Flagrant podcast in a wide-ranging conversation that covers her explosive performance at the Kevin Hart Roast on Netflix, her Air Force service, and her decades-long comedy career. Underwood reveals that Tony Hinchcliffe warned her before the roast that he planned to joke about her husband's suicide and sexual assault, to which she responded that the jokes better be funny. She also discloses that she was praying and improvising on stage during the roast, sitting next to Hinchcliffe with paper and pen, writing new material in real time. The conversation explores Underwood's military background, including a shocking moment at Yokosuka Naval Base in Japan where an admiral told her the military couldn't protect her from sailors who had been at sea for 40 days and were worked up by her sexual comedy material. Underwood discusses being labeled a homophobe by GLAAD for a joke comparing male anatomy to Secret Deodorant, and shares intimate stories about being mentored by Bernie Mac in Chicago's comedy scene, where Mac was known by his nickname Blue. Throughout the episode, Underwood addresses criticism that she sold out by participating in the roast, arguing instead that she defended Black culture while creating opportunities for other comedians. She emphasizes her belief that all relationships are transactions, discusses her conservative political views as a Republican, and explains her philosophy that she's never the breadwinner in relationships regardless of her income. The conversation touches on comedy economics, the need for more content creation by female comics, and Underwood's vision for bringing variety show entertainment back to television through her Great American Talent Search tour.
Key takeaways
- Sheryl Underwood reveals Tony Hinchcliffe warned her before the Kevin Hart Roast that he would joke about her husband's suicide and sexual assault, and she told him the material better be funny.
- Underwood discloses she was praying and improvising during the roast, sitting next to Hinchcliffe with paper and pen writing new material in real time rather than following a completely scripted performance.
- The comedian recounts a military admiral at Yokosuka Naval Base telling her the US military couldn't protect her from sailors after 40 days at sea who were worked up by her sexual comedy material.
- Underwood reveals GLAAD labeled her a homophobe on their website for a Comic View joke comparing male anatomy to Secret Deodorant that she believed was about civil rights.
- The comedian shares being mentored by Bernie Mac in Chicago's comedy scene, where Mac was nicknamed Blue for his dark complexion and taught young comics professionalism and stage presence.
- Underwood defends participating in the controversial Kevin Hart Roast, arguing she defended Black culture while creating downstream opportunities for other comedians rather than selling out.
- The Air Force veteran discusses her conservative Republican politics, her belief that all relationships are transactions, and her philosophy that men should always be the breadwinner regardless of her higher income.