Sheryl Underwood

Sheryl Underwood is a stand-up comedian and longtime daytime talk show host. She has never filmed a nude scene, and this archive makes no such claim. Her single video on CelebMasta comes from the 2025 edition of Hollywood Squares. The title bills a lesbian scene shared with Drew Barrymore, Tiffany Haddish, Whitney Cummings and Tyra Banks. In practice it is a scripted comedy bit between panelists, nothing revealing. Underwood plays the gag for laughs, which is how she has worked her whole career. Her page holds that one group clip rather than any solo material. The entire collection is that single Hollywood Squares segment from 2025.

Sheryl Underwood shares scenes with Drew Barrymore, Tiffany Haddish and Tyra Banks on CelebMasta.