CBS · To Be Determined

Hollywood Squares

2025 · Rated 6.8/10

Last aired: S2 E22, Snooze We Can't Lose · 2026-05-27

Hollywood Squares involves two contestants who 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.

Cast

Nate Burleson Host

Drew Barrymore Center Square

Season 2

Season 1 Season 2

E1 Santa's Got a Little Game 2025-12-22 · 30 min Ed, a woodworker/Santa from Middletown, N.Y., and Katie, a server from Philadelphia, Pa., take turns asking questions to celebrity squares: Tichina Arnold, Michelle Buteau, Ana Gasteyer, Pete Holmes, Triumph the Insult Comic Dog, Thomas Lennon, Bobby Moynihan and Meghan Trainor.

E2 Hand This Man a Candy Cane 2025-12-22 · 30 min Joshua, a martial arts instructor from Philadelphia, Pa., and Alisha, an Army vet/government contractor from Redlands, Calif., take turns asking questions to celebrity squares: Tichina Arnold, Michelle Buteau, Ana Gasteyer, Pete Holmes, Triumph the Insult Comic Dog, Thomas Lennon, Tim Meadows and Bobby Moynihan.

E3 I Will Not Be Ignored, Glenn! 2026-01-07 · 30 min Celebrity contestants Anthony Anderson, Glenn Close, Pete Holmes, Whitney Cummings, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Ross Mathews.

E4 Between a Cardigan Sandwich 2026-01-07 · 30 min Celebrity contestants Whitney Cummings, Kat Dennings, Fortune Feimster, Pete Holmes, Tiffany Haddish, Padma Lakshmi, Joel McHale and RuPaul.

E5 This Is the Best Show on TV 2026-01-14 · 30 min Celebrity contestants Whitney Cummings, Ariana Debose, Fortune Feimster, Tiffany Haddish, Arsenio Hall, Lil Rel Howery, Jo Koy and Ms. Pat.

E6 I'm Terrified of Triumph 2026-01-14 · 30 min Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Zarna Garg, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Jay Mohr.

E7 Expect the Unexpected 2026-01-21 · 30 min Celebrity guests Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Julie Chen Moonves, Jason Ritter and Kristen Schaal.

E8 This Always Happens When RuPaul's Around 2026-01-21 · 30 min Celebrity guests Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul.

E9 The Legacy Show 2026-01-28 · 30 min Celebrity guests Tom Bergeron, Whitney Cummings, Tiffany Haddish, Arsenio Hall, Howie Mandel, Thomas Lennon, Leslie Jones and Triumph the Insult Comic Dog.

E10 I Didn't Know You Were that Flexible 2026-01-28 · 30 min Celebrity guests Whitney Cummings, Fortune Feimster, Zarna Garg, Tiffany Haddish, Robby Hoffman, Padma Lakshmi, Thomas Lennon, Bill Maher, Joel McHale and Triumph the Insult Comic Dog.

E11 Thicker Than A 1st Grade Pencil 2026-02-04 · 30 min Celebrity guests Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer.

E12 I Have a Lot of Exes Watching Right Now 2026-02-04 · 30 min Celebrity guests Ariana DeBose, Ron Funches, Gabriel "Fluffy" Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash‑Betts, Ms. Pat and Paul Scheer.

E13 A Scream Reunion 2026-02-22 · 30 min Celebrity guests David Arquette, Whitney Cummings, Mark Duplass, Tiffany Haddish, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Thomas Lennon.

E14 I'm Nasty, But I Ain't No Hero 2026-02-22 · 30 min Celebrity guests Whitney Cummings, Ariana Debose, Fortune Feimster, Ryan Fitzpatrick, Tiffany Haddish, Lil Rel Howery, Gabriel Iglesias and Jo Koy.

E15 This Isn't Survivor 2026-03-11 · 30 min Celebrity guests Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash‑Betts and Ms. Pat.

E16 There's That Cruella Energy 2026-03-18 · 30 min Celebrity contestants Neal Brennan, Glenn Close, Whitney Cummings, Robby Hoffman, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Howie Mandel.

E17 Please Don't Let it Be a Hawk 2026-03-25 · 30 min Celebrity contestants Tichina Arnold, Michelle Buteau, Tony Hawk, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.

E18 90s Fine Baby 2026-04-08 · 30 min Celebrity contestants Tichina Arnold, Michelle Buteau, Method Man, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.

E19 We Have a Lot of SNL Funny in Here Tonight 2026-04-15 · 30 min Celebrity contestants Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Chris Redd, Jason Ritter and Kristen Schaal.

E20 Be Careful What You Ask for Howie 2026-04-22 · 30 min Celebrity contestants Whitney Cummings, Mark Duplass, Ana Gasteyer, Tiffany Haddish, Triumph the Insult Comic Dog, Leslie Jones, Thomas Lennon, Howie Mandel and Ross Mathews.

E21 The Wizard of Hollywood Squares 2026-05-06 · 30 min Celebrity contestants Michelle Buteau, Kat Dennings, Tiffany Haddish, Pete Holmes, Thomas Lennon, Bobby Moynihan, Law Roach and Meghan Trainor.

E22 Snooze We Can't Lose 2026-05-27 · 30 min Celebrity contestants Tom Bergeron, Neal Brennan, Whitney Cummings, Ariana Debose, Mark Duplass, Arsenio Hall, Tiffany Haddish and Ms. Pat.

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