Underwood Stayed Sober Through Tom Brady Roast to Remember Working With Colleagues
"I wanted to enjoy the high of working with my colleagues. That's what I want to experience it without alcohol in my system so I can remember it."
About this episode
Comedian Sheryl Underwood joined hosts Matt McCusker and Shane Gillis on Matt and Shane's Secret Podcast for a wide-ranging conversation that moved from the mechanics of the Tom Brady roast to deeply personal revelations about trauma, politics, and relationships. Underwood disclosed that she was sexually assaulted and chose to process the trauma publicly through stand-up comedy, explaining that the stage became her therapeutic outlet. She also discussed her late husband's suicide by jumping off a building, acknowledging that while she didn't cause his death, therapy revealed she may have exacerbated his stress—a realization that now informs her comedy about relationships. The conversation addressed the controversial George Floyd joke Tony Hinchcliffe made at the roast, with Underwood defending her decision not to respond on stage and articulating a comedian's code: without a devastating comeback, silence is preferable to undermining the moment. Underwood revealed she has been a registered Republican for decades but is now labeled a RINO during the Trump administration and called transphobic and homophobic, labels she says don't bother her. She explained her unusual decision to remain completely sober through the Brady roast to remember working with colleagues, breaking her typical pattern of drinking to wind down after performances. The episode also covered her dating philosophy, her belief in separate living arrangements even in marriage, and her upcoming projects including a Netflix special, the I Need a Job comedy tour, and Sheryl Underwood's Great American Talent Search, which she envisions as a multi-genre community talent competition crossing all formats of music and performance.
Key takeaways
- Underwood disclosed she was raped and chose to process the trauma publicly through stand-up comedy because the stage was her most comfortable space.
- She acknowledged in therapy that while she didn't kill her husband, she may have exacerbated his stress before his suicide by jumping off a building.
- Underwood defended not responding to Tony Hinchcliffe's George Floyd roast joke, explaining that without a devastating comeback, silence prevents setting back the cause.
- She revealed being a registered Republican for decades but is now called a RINO, transphobic, and homophobic during the Trump administration.
- Underwood stayed completely sober through the Tom Brady roast to remember the experience of working with top comedians, breaking her usual post-show drinking pattern.
- She articulated a dating philosophy that includes separate living arrangements even in marriage and the importance of giving men space instead of constant communication.
- Underwood is launching Sheryl Underwood's Great American Talent Search, a multi-genre community talent competition that will start with preliminary rounds in comedy clubs.