Wanda Sykes, the guest on this episode of The Hollywood Reporter’s Awards Chatter podcast, is a trailblazing stand-up comedian, actress and writer who has to her name 17 Emmy nominations and one win; was picked by Entertainment Weekly as one of the 25 funniest people in America and Comedy Central as one the 100 greatest stand-ups of all-time; and is now, for her seventh hourlong stand-up special, Netflix’s Wanda Sykes: Legacy, back in Emmys contention.
Over the course of a conversation at the L.A. offices of The Hollywood Reporter, the 62-year-old opened up about what prompted her, at the age of 27, to leave a steady job with benefits at the National Security Agency to pursue a career as a stand-up; how her comedy changed after she divorced her husband in 1998 en route to coming out as a lesbian in 2008; and some of the hot-button comedy issues of recent years, many of which she has had a front-row seat to: the firing of Roseanne Barr during the making of the reboot of the TV series Roseanne, which she was a part of; the slapping of her friend and mentor Chris Rock by Will Smith at the 2022 Oscars ceremony that she co-hosted; and the targeting by President Trump of comedians including Jimmy Kimmel, on whose late-night show she was set to appear as a guest the night Kimmel got pulled off the air in 2025.
