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Hollywood Squares - S02E01 - Santa's Got a Little Game (High MP4) (WEBM) (Aired: 2025-12-21) Celebrity contestants Tim Meadows, Meghan Trainor, Tichina Arnold, Michelle Buteau, Ana Gasteyer, Thomas Lennon, Bobby Moynihan, Pete Holmes and Triumph the Insult Comic Dog. Stars: Tichina Arnold, Drew Barrymore, Nate Burleson Director(s): Writer(s): |
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Hollywood Squares - S02E02 - Hand This Man a Candy Cane (High MP4) (WEBM) (Aired: 2025-12-21) Celebrity contestants Tim Meadows, Meghan Trainor, Tichina Arnold, Michelle Buteau, Ana Gasteyer, Thomas Lennon, Bobby Moynihan, Pete Holmes and Triumph the Insult Comic Dog. Stars: Tichina Arnold, Drew Barrymore, Nate Burleson Director(s): Writer(s): |
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Hollywood Squares - S02E03 - I Will Not Be Ignored, Glenn! (High MP4) (WEBM) (Aired: 2026-1-7) Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Pete Holmes, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Ross Mathews. Stars: Anthony Anderson, Drew Barrymore, Nate Burleson Director(s): Writer(s): |
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Hollywood Squares - S02E04 - Between a Cardigan Sandwich (High MP4) (WEBM) (Aired: 2026-1-7) Celebrity contestants Whitney Cummings, Kat Dennings, Fortune Feimster, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Joel McHale and RuPaul. Stars: Drew Barrymore, Nate Burleson, Whitney Cummings Director(s): Writer(s): |
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Hollywood Squares - S02E05 - This Is the Best Show on TV (High MP4) (WEBM) (Aired: 2026-1-14) Stars: Drew Barrymore, Nate Burleson, Whitney Cummings Director(s): Writer(s): |
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Hollywood Squares - S02E06 - I'm Terrified of Triumph (High MP4) (WEBM) (Aired: 2026-1-14) Stars: Nate Burleson, Anthony Anderson, Drew Barrymore Director(s): Writer(s): |
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Hollywood Squares - S02E07 - Expect the Unexpected (High MP4) (WEBM) (Aired: 2026-1-21) Stars: Nate Burleson, Drew Barrymore, Tichina Arnold Director(s): Writer(s): |
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Hollywood Squares - S02E08 - This Always Happens When RuPaul's Around (High MP4) (WEBM) (Aired: 2026-1-21) Stars: Nate Burleson, Drew Barrymore, Whitney Cummings Director(s): Writer(s): |
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Hollywood Squares - S02E09 - The Legacy Show (High MP4) (WEBM) (Aired: 2026-1-28) Stars: Nate Burleson, Drew Barrymore, Tom Bergeron Director(s): Writer(s): |
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Hollywood Squares - S02E10 - I Didn't Know You Were that Flexible (High MP4) (WEBM) (Aired: 2026-1-28) Stars: Nate Burleson, Drew Barrymore, Whitney Cummings Director(s): Writer(s): |
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Hollywood Squares - S02E11 - Thicker Than a 1st Grade Pencil (High MP4) (Aired: 2026-2-4) Celebrity Squares: Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer. Contestants: Jake from Los Angeles, Calif., and Moni from Montgomery, Ala. Stars: Nate Burleson, Drew Barrymore, Michelle Buteau Director(s): Writer(s): |
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Hollywood Squares - S02E12 - I Have a Lot of Exes Watching Right Now (High MP4) (Aired: 2026-2-4) Celebrity Squares: Ariana DeBose, Ron Funches, Gabriel \"Fluffy\" Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash Betts, Ms. Pat and Paul Scheer. Contestants: Johnnie from Ft. Pierce, Fla., and Casey from San Diego, Calif. Stars: Nate Burleson, Drew Barrymore, Ariana DeBose Director(s): Writer(s): |
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Hollywood Squares - S02E13 - This Isn't Survivor (High MP4) (Aired: 2026-3-11) Celebrity Squares: Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash Betts and Ms. Pat. Contestants: Jared from Marlton, N.J., and Danielle from West Hills, Calif. Stars: Drew Barrymore, Nate Burleson, Ariana DeBose Director(s): Writer(s): |
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Hollywood Squares - S02E14.avi (High MP4) Stars: Director(s): Writer(s): |
