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Video: RuPaul Stars in Sneak Peek From Upcoming Episode of HOLLYWOOD SQUARES

Titled, “This Always Happens When RuPaul’s Around,” the episode will air Wednesday, Jan. 21 (8:30-9:00 PM, ET/PT) on CBS.

By: Jan. 15, 2026



Check out a sneak peek clip from the upcoming episode of Hollywood Squares, featuring Drag Race icon RuPaul. In the new episode, RuPaul is featured as a celebrity guest alongside Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, and Joel McHale.

Titled, “This Always Happens When RuPaul’s Around,” the episode will air Wednesday, Jan. 21 (8:30-9:00 PM, ET/PT) on CBS and will be available to stream on Paramount+. Contestants for the episode are Eric from Baltimore, Md., and Siranda from La Cañada, Calif.

The first episode of the night, beginning at 8:00, will feature Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Julie Chen Moonves, Jason Ritter, and Kristen Schaal.

Hollywood Squares, starring Drew Barrymore, is a new version of the classic game show in which two contestants play tic-tac-toe to win money and prizes. The “board” for the game is a vertical stack of open-faced cubes, each occupied by a celebrity seated at a desk and facing the contestants. The celebrities are asked questions and the contestants judge the legitimacy of their answers to win the game. In this season, Nate Burleson returns as host with Drew Barrymore starring as the famed center square.

Photo Credit: Matthew Taplinger/CBS


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