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Hollywood Squares
Ended★5.4· 387 votesIMDbTVDB
2 seasons · 41 episodes
A reboot of Hollywood Squares. A game show where celebrities face contestants, seated at desks arranged vertically. Contestants judge the celebrities' responses to questions to determine winners.
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Episodes

Season 2 - Episodes

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Hollywood Squares
S02E01Santa's Got a Little Game
Aired: 2025-12-21
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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
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Hollywood Squares
S02E02Hand This Man a Candy Cane
Aired: 2025-12-21
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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
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Hollywood Squares
S02E03I Will Not Be Ignored, Glenn!
Aired: 2026-1-7
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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
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Hollywood Squares
S02E04Between a Cardigan Sandwich
Aired: 2026-1-7
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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
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Hollywood Squares
S02E05This Is the Best Show on TV
Aired: 2026-1-14
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Hollywood Squares
S02E06I'm Terrified of Triumph
Aired: 2026-1-14
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Hollywood Squares
S02E07Expect the Unexpected
Aired: 2026-1-21
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Hollywood Squares
S02E08This Always Happens When RuPaul's Around
Aired: 2026-1-21
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Hollywood Squares
S02E09The Legacy Show
Aired: 2026-1-28
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Hollywood Squares
S02E10I Didn't Know You Were that Flexible
Aired: 2026-1-28
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Hollywood Squares
S02E11Thicker Than a 1st Grade Pencil
Aired: 2026-2-4
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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
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Hollywood Squares
S02E12I Have a Lot of Exes Watching Right Now
Aired: 2026-2-4
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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
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Hollywood Squares
S02E13This Isn't Survivor
Aired: 2026-3-11
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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
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Hollywood Squares
S02E14Hollywood Squares - S02E14.avi
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Hollywood Squares
S02E15Hollywood Squares - S02E15.avi
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Hollywood Squares
S02E16There's That Cruella Energy
Aired: 2026-03-18
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Celebrity guests Neal Brennan, Glenn Close, Whitney Cummings, Robby Hoffman, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones, and Howie Mandel;

Stars: Nate Burleson, Drew Barrymore, Neal Brennan
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Hollywood Squares
S02E17Please Don't Let It Be a Hawk
Aired: 2026-03-25
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Celebrities Tichina Arnold, Michelle Buteau, Tony Hawk, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd, and Paul Scheer;

Stars: Nate Burleson, Drew Barrymore, Tichina Arnold
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Hollywood Squares
S02E1890s Fine Baby
Aired: 2026-04-08
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Celebrities Tichina Arnold, Michelle Buteau, Method Man, Triumph the Insult Dog, Janelle James, Tig Notaro, Chris Redd, and Paul Scheer;

Stars: Nate Burleson, Drew Barrymore, Tichina Arnold
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Hollywood Squares
S02E19We Have a Lot of SNL Funny in Here Tonight
Aired: 2026-04-15
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Celebrities Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Chris Redd, Jason Ritter, and Kristen Schaal;

Stars: Nate Burleson, Drew Barrymore, Tichina Arnold
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Hollywood Squares
S02E20Be Careful What You Ask for Howie
Aired: 2026-04-22
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Celebrities Whitney Cummings, Mark Duplass, Ana Gasteyer, Tiffany Haddish, Triumph the Insult Comic Dog, Leslie Jones, Thomas Lennon, Howie Mandel, and Ross Mathews;

Stars: Nate Burleson, Drew Barrymore, Whitney Cummings
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Hollywood Squares
S02E21The Wizard of Hollywood Squares
Aired: 2026-05-06
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Celebrities Michelle Buteau, Kat Dennings, Tiffany Haddish, Pete Holmes, Thomas Lennon, Bobby Moynihan, Law Roach, and Meghan Trainor;

Stars: Nate Burleson, Drew Barrymore, Michelle Buteau