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Episode Notes
Sheryl Underwood reveals what really happened at The Roast of Kevin Hart, the advice Tupac gave her that changed her career, and how she survived decades in comedy by staying fearless, funny, and impossible to ignore.
On this episode of Byron Scott’s Fast Break, Sheryl Underwood joins Byron Scott and Jay Wagers for a wild, hilarious, and deeply personal conversation about her legendary career. Sheryl breaks down the pressure of walking into The Roast of Kevin Hart, why Nikki Glaser warned her backstage, what it felt like when Shane Gillis and Tony Hinchcliffe came after her, and why she walked away feeling like they “shot at the queen and missed.”
She also shares stories from Def Comedy Jam, The Talk, BET, and the comedy club grind, including career-changing advice from Tupac, a classic Kobe Bryant moment at Roscoe’s, Steve Harvey pushing her toward The Talk, Flavor Flav escorting her at the BET Comedy Awards, David Alan Grier costing her a possible NFL relationship, and why she believes she’s still one of the most underrated comedians ever.
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"Sheryl Underwood | The Kevin Hart Roast" is an episode of Byron Scott's Fast Break. Runtime 1 hr 22 min. Published June 17, 2026. Hit play above to stream it here, or open the free Spot Sports app for background play and offline downloads.
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Quick FAQ
- When was this episode published?
- June 17, 2026.
- How long is this episode?
- 1 hr 22 min.
- What podcast is this from?
- Byron Scott's Fast Break. Browse the full back catalog on the show page.
- What does this episode cover?
- Byron Scott's Fast Break covers basketball. This episode runs on the show's regular cadence.
