Hollywood Squares

Watch Hollywood Squares

  • 2025
  • 2 Seasons
  • 5.2  (247)

A 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.

Hollywood Squares is a series that ran for 2 seasons (41 episodes) between January 16, 2025 and on

Hollywood Squares
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Seasons
We Have a Lot of SNL Funny in Here Tonight
19. We Have a Lot of SNL Funny in Here Tonight
April 15, 2026
Celebrity contestants Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Chris Redd, Jason Ritter and Kristen Schaal.
90s Fine Baby
18. 90s Fine Baby
April 8, 2026
Celebrity contestants Tichina Arnold, Michelle Buteau, Method Man, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.
Please Don't Let it Be a Hawk
17. Please Don't Let it Be a Hawk
March 25, 2026
Celebrity contestants Tichina Arnold, Michelle Buteau, Tony Hawk, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.
There's That Cruella Energy
16. There's That Cruella Energy
March 18, 2026
Celebrity contestants Neal Brennan, Glenn Close, Whitney Cummings, Robby Hoffman, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Howie Mandel.
This Isn't Survivor
15. This Isn't Survivor
March 11, 2026
Celebrity guests Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash‑Betts and Ms. Pat.
I'm Nasty, But I Ain't No Hero
14. I'm Nasty, But I Ain't No Hero
February 22, 2026
Celebrity guests Whitney Cummings, Ariana Debose, Fortune Feimster, Ryan Fitzpatrick, Tiffany Haddish, Lil Rel Howery, Gabriel Iglesias and Jo Koy.
A Scream Reunion
13. A Scream Reunion
February 22, 2026
Celebrity guests David Arquette, Whitney Cummings, Mark Duplass, Tiffany Haddish, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Thomas Lennon.
I Have a Lot of Exes Watching Right Now
12. I Have a Lot of Exes Watching Right Now
February 4, 2026
Celebrity guests Ariana DeBose, Ron Funches, Gabriel "Fluffy" Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash‑Betts, Ms. Pat and Paul Scheer.
Thicker Than A 1st Grade Pencil
11. Thicker Than A 1st Grade Pencil
February 4, 2026
Celebrity guests Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer.
I Didn't Know You Were that Flexible
10. I Didn't Know You Were that Flexible
January 28, 2026
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.
The Legacy Show
9. The Legacy Show
January 28, 2026
Celebrity guests Tom Bergeron, Whitney Cummings, Tiffany Haddish, Arsenio Hall, Howie Mandel, Thomas Lennon, Leslie Jones and Triumph the Insult Comic Dog.
This Always Happens When RuPaul's Around
8. This Always Happens When RuPaul's Around
January 21, 2026
Celebrity guests Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul.
Expect the Unexpected
7. Expect the Unexpected
January 21, 2026
Celebrity guests Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Julie Chen Moonves, Jason Ritter and Kristen Schaal.
I'm Terrified of Triumph
6. I'm Terrified of Triumph
January 14, 2026
Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Zarna Garg, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Jay Mohr.
This Is the Best Show on TV
5. This Is the Best Show on TV
January 14, 2026
Celebrity contestants Whitney Cummings, Ariana Debose, Fortune Feimster, Tiffany Haddish, Arsenio Hall, Lil Rel Howery, Jo Koy and Ms. Pat.
Between a Cardigan Sandwich
4. Between a Cardigan Sandwich
January 7, 2026
Celebrity contestants Whitney Cummings, Kat Dennings, Fortune Feimster, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Joel McHale and RuPaul.
I Will Not Be Ignored, Glenn!
3. I Will Not Be Ignored, Glenn!
January 7, 2026
Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Pete Holmes, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Ross Mathews.
Hand This Man a Candy Cane
2. Hand This Man a Candy Cane
December 22, 2026
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.
Santa's Got a Little Game
1. Santa's Got a Little Game
December 22, 2026
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.
Description
Where to Watch Hollywood Squares
Hollywood Squares is available for streaming on the website, both individual episodes and full seasons. You can also watch Hollywood Squares on demand at Apple TV Channels, Paramount+, Prime Video, FuboTV and Pluto TV.
  • Genres
    Game-Show
  • Cast
    Nate Burleson
    Drew Barrymore
    Whitney Cummings
  • Premiere Date
    January 16, 2025
  • IMDB Rating
    5.2  (247)
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