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 (30 episodes) between January 16, 2025 and on

Hollywood Squares
Filter by Source
Seasons
I Didn't Know You Were that Flexible
8. 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
7. 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
6. 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
5. 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
4. 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
3. 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
2. 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!
1. 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.
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)
If You Like Hollywood Squares, Then Try...
Pop Culture Jeopardy!
Red Carpet Survival
The Traitors: NZ
Tenable
Limitless Win UK
Stab That Cake!
Whose Line Is It Anyway? Australia
Buddy Games
Superstar Dogs
Match Game
Top TV Shows
Yo Gabba Gabba
Fraggle Rock
IT: Welcome To Derry
Euphoria
Landman
Carpool Karaoke
The Rookie
American Monster
Jeopardy!
The View
The Pitt