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TV series

Hollywood Squares

Latest episode

S2 E22 · Snooze We Can't Lose

About Hollywood Squares

Hollywood Squares is a reality TV series that premiered on CBS on January 16, 2025. It has 2 seasons and 36 episodes so far and is still airing new episodes. The latest episode, Season 2 Episode 22 "Snooze We Can't Lose", aired on May 27, 2026.

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.

  • Reality

Last updated

Episodes

36 episodes · 2 seasons

Season 1

2025 · 20 episodes · Last episode: 1 year ago

Hollywood Squares Season 1 release dates →
  1. Hollywood Squares S1 E20 still E20

    20. Between Two Nuts

    Celebrity guests include Luenell, Debi Mazar, Jack McBrayer, Patton Oswalt, Ravi Patel, Mira Sorvino, Michaela Watkins, and Reggie Watts.

  2. Hollywood Squares S1 E19 still E19

    19. I’ve Been in 12 Sandwiches

    Celebrity guests include Tichina Arnold, Beth Behrs, Mario Cantone, Pete Holmes, Jo Koy, Tig Notaro, June Diane Raphael, and Kristen Schaal,

  3. Hollywood Squares S1 E18 still E18

    18. I’d Lick That Stamp

    Guests include Tiffany Haddish, Justin Long, Marsai Martin, Kevin Nealon, Jimmy O Yang, Dusty Slay, JB Smoove and Casey Wilson.

  4. Hollywood Squares S1 E17 still E17

    17. That’s Dad Math

    Guests include Tichina Arnold, Annaleigh Ashford, Mario Cantone, Jo Koy, Vicky Lawrence, Tig Notaro, Russell Peters and Andrew Rannels.

  5. Hollywood Squares S1 E16 still E16

    16. I Can't Find My Wallet

    Celebrity guests: Tichina Arnold, Mario Cantone, Jo Koy, Loni Love, Melanie Lynskey, Tig Notaro, June Diane Raphael and Jason Ritter.

  6. Hollywood Squares S1 E15 still E15

    15. You Lost Me at Nachos

    Celebrity guests: Yvette Nicole Brown, Whitney Cummings, Oliver Hudson, Gabriel "Fluffy" Iglesias, Triumph the Insult Comic Dog, Phil Keoghan, Loni Love and Sheryl Underwood.

  7. Hollywood Squares S1 E14 still E14

    14. You Like Granny Panties

    Celebrity guests: Yvette Nicole Brown, Whitney Cummings, Akbar Gbajabiamila, Oliver Hudson, Gabriel "Fluffy" Iglesias, Triumph the Insult Comic Dog, Sam Jay and Ross Mathews.

  8. Hollywood Squares S1 E13 still E13

    13. A Little Doggy Gave It to Me

    Celebrity guests: Tichina Arnold, Beth Behrs, Whitney Cummings, Tony Gonzalez, Triumph the Insult Comic Dog, Ross Mathews, Kevin Nealon and Aida Rodriguez.

  9. Hollywood Squares S1 E12 still E12

    12. It's a Wooden American

    Celebrity guests: Tyra Banks, Jeff Dunham, Ron Funches, Tiffany Haddish, Justin Long, Chelsea Peretti, Jay Pharoah and Dusty Slay.

  10. Hollywood Squares S1 E11 still E11

    11. Let's Not Fight in Front of Wiz Khalifa

    Celebrity guests: Whitney Cummings, Andra Day, Mickey Guyton, Pete Holmes, Wiz Khalifa, Jay Leno, Thomas Lennon and Dionne Warwick.

  11. Hollywood Squares S1 E10 still E10

    10. I'm Going to the Wrong Doctor

    Celebrity guests Whitney Cummings, Tiffany Haddish, Kathy Hilton, Triumph the Insult Comic Dog, Thomas Lennon, Ms. Pat, JB Smoove and Casey Wilson.

  12. Hollywood Squares S1 E9 still E9

    9. Ex's Get the Square

    Celebrity guests Mayim Bialik, Tiffany Haddish, Pete Holmes, Justin Long, Marsai Martin, Jimmy O. Yang, Kristen Schaal and JB Smoove.

  13. Hollywood Squares S1 E8 still E8

    8. They Always Choose Me, Boo!

    Julie Bowen, Margaret Cho, Leslie Jones, Carson Kressley, Jeannie Mai, Kevin Nealon, RuPaul and Paul Scheer

  14. Hollywood Squares S1 E7 still E7

    7. It's a Hot Gentleman's Sweater

    Nicole Byer, Drew Carey, Luenell, Debi Mazar, Bobby Moynihan, Chelsea Peretti, Phil Rosenthal and JB Smoove

  15. Hollywood Squares S1 E6 still E6

    6. The Price Was Wrong Drew

    Celebs Drew Carey, Max Greenfield, Rita Moreno, Bobby Moynihan, Pete Holmes, Lil Rel, Nicole Byer, and Jeff Dunham.

  16. Hollywood Squares S1 E5 still E5

    5. Didn't Work If Nelly Didn't Laugh

    Celebs Chaka Khan, Jay Leno, Tanner Adell, Whitney Cummings, Pete Holmes, Patton Oswalt, Nelly, Thoms Lennon.

  17. Hollywood Squares S1 E4 still E4

    4. Sixty for Swifty

    Celebs Julie Bowen, Margaret Cho, Leslie Jones, Carson Kressley, Ross Mathews, Kevin Nealon, RuPaul and Paul Scheer.

  18. Hollywood Squares S1 E3 still E3

    3. It's a Kiss Party

    Celebs Triumph The Insult Comic Dog, Sam Jay, Whitney Cummings, Tyra Banks, Tiffany Haddish, Sheryl Underwood, Thomas Lennon and Drew Barrymore.

  19. Hollywood Squares S1 E2 still E2

    2. The Mayor of the Sun

    Celebs Drew Barrymore, Drew Carrey, Bobby Moynihan, JB Smoove, Chelsea Peretti, Tichina Arnold, Nicole Byer, Debi Mazar, and Pete Holmes.

  20. Hollywood Squares S1 E1 still E1

    1. It's a Dysfunctional Family Show

    Celebs Drew Barrymore, Triumph the Insult Comic Dog, Julie Bowen, Whitney Cummings, Thomas Lennon, Ms. Pat, Tiffany Haddish, Tyra Banks, and Jeff Ross.

Season 2

2025 · 22 episodes · Last episode: 5 months ago

Hollywood Squares Season 2 release dates →
  1. E22

    22. Snooze We Can't Lose

    Celebrities Tom Bergeron, Neal Brennan, Whitney Cummings, Ariana DeBose, Mark Duplass, Arsenio Hall, Tiffany Haddish and Ms. Pat.

  2. E21

    21. The Wizard of Hollywood Squares

    Celebrities Michelle Buteau, Kat Dennings, Tiffany Haddish, Pete Holmes, Thomas Lennon, Bobby Moynihan, Law Roach and Meghan Trainor.

  3. E20

    20. Be Careful What You Ask for Howie

    Celebrities Whitney Cummings, Mark Duplass, Ana Gasteyer, Tiffany Haddish, Triumph the Insult Comic Dog, Leslie Jones, Thomas Lennon, Howie Mandel and Ross Mathews.

  4. E19

    19. We Have a Lot of SNL Funny in Here Tonight

  5. E18

    18. 90s Fine Baby

  6. E17

    17. Please Don't Let It Be a Hawk

  7. E16

    16. There’s That Cruella Energy

  8. E15

    15. This Isn’t Survivor

  9. E14

    14. I’m Nasty, But I Ain’t No Hero

  10. E13

    13. A Scream Reunion

  11. E12

    12. I Have a Lot of Exes Watching Right Now

  12. E11

    11. Thicker Than a 1st Grade Pencil

  13. E10

    10. I Didn’t Know You Were That Flexible

  14. E9

    9. The Legacy Show

  15. E8

    8. This Always Happens When RuPaul’s Around

  16. E7

    7. Expect the Unexpected

  17. E6

    6. I'm Terrified of Triumph

  18. E5

    5. This Is the Best Show on TV

  19. E4

    4. Between a Cardigan Sandwich

  20. E3

    3. I Will Not Be Ignored, Glenn!

  21. E2

    2. Hand This Man a Candy Cane

  22. E1

    1. Santa's Got a Little Game

Cast & crew

  • Tyra Banks

    Tyra Banks

    Self

  • Julie Bowen

    Julie Bowen

    Self

  • Whitney Cummings

    Whitney Cummings

    Self

  • Tiffany Haddish

    Tiffany Haddish

    Self

  • Thomas Lennon

    Thomas Lennon

    Self

  • Patricia Williams

    Patricia Williams

    Self

  • Tichina Arnold

    Tichina Arnold

    Self

  • Nicole Byer

    Nicole Byer

    Self

  • Drew Carey

    Drew Carey

    Self

  • Pete Holmes

    Pete Holmes

    Self

  • Debi Mazar

    Debi Mazar

    Self

  • Bobby Moynihan

    Bobby Moynihan

    Self

  • Chelsea Peretti

    Chelsea Peretti

    Self

  • Jeff Ross

    Jeff Ross

    Self

  • Robert Smigel

    Robert Smigel

    Triumph the Insult Comic Dog (voice)

  • JB Smoove

    JB Smoove

    Self

Hollywood Squares FAQ

When is the next episode of Hollywood Squares?

A date for the next episode of Hollywood Squares hasn't been announced yet. Follow Hollywood Squares in the Streambay app and you'll be notified as soon as a new episode airs.

When did the latest episode of Hollywood Squares come out?

The most recent episode of Hollywood Squares, Season 2 Episode 22 "Snooze We Can't Lose", aired on May 27, 2026.

How many seasons of Hollywood Squares are there?

Hollywood Squares has 2 seasons with 36 episodes in total.

When did Hollywood Squares first air?

Hollywood Squares first aired on CBS on January 16, 2025.

How do I get notified when new episodes of Hollywood Squares are released?

Download the Streambay app, follow Hollywood Squares, and you'll get a push notification the moment each new episode is released.

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