On May 21, 2026, Sheryl Underwood criticized comedians Tony Hinchcliffe and Shane Gillis in an interview, marking a sharp turn from her recent celebratory appearance on Kill Tony.
During that appearance, Tony Hinchcliffe hyped up her career momentum alongside Tom Segura. Hinchcliffe introduced her as "fresh off of the Roast of Kevin Hart" and noted she was "immediately signed to a one-hour special produced by Kevin Hart, brought to you by Netflix."
The atmosphere turned to friendly teasing when Tony Hinchcliffe shared a backstage rumor, saying that Joe Rogan told him, "Fun fact about Sheryl Underwood: she always keeps her purse on her". For her part, Sheryl Underwood wasn't shy about roasting the room, taking a jab at Pat O'Neill by comparing his appearance to Heidi, quipping, "See, when Heidi came out, only thing I thought was it's the before and after of-"
But the goodwill didn't last long outside the comedy club walls. With Sheryl Underwood now taking aim at Tony Hinchcliffe and Shane Gillis in the press, it remains to be seen whether her high-profile Netflix deal will bridge the gap or if this marks a permanent split from the Austin podcast circle.