When does Hollywood Squares air next?

Hollywood Squares airs next on Thu, Apr 23 2026 2:30 AM GMT+0000.

How many seasons does Hollywood Squares have?

Hollywood Squares has 2 seasons with 42 episodes.

When did Hollywood Squares premiere?

Hollywood Squares premiered on January 16, 2025.

Hollywood Squares

Name: Hollywood Squares
Rating: 6.8
Cast: Nate Burleson, Drew Barrymore

6.8/10

CBS Running

2 Seasons · 42 Episodes · Premiered January 16, 2025

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.

Where to Watch: CBS

Official Site

Next Air Time: Thu, Apr 23 2026 2:30 AM GMT+0000

Seasons & Episodes

Season 1

20 episodes

E01

It's a Dysfunctional Family Show

Fri, Jan 17 2025 1:00 AM GMT+0000 30 min

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

E02

The Mayor of the Sun

Fri, Jan 17 2025 1:30 AM GMT+0000 30 min

Tichina Arnold; Nicole Byer; Drew Carey; Pete Holmes; Debi Mazar; Bobby Moynihan; Chelsea Peretti.

E03

It's a Kiss Party

Mon, Jan 20 2025 3:00 AM GMT+0000 30 min

Tyra Banks; Whitney Cummings; Tiffany Haddish; Sam Jay; Thomas Lennon; Triumph the Insult Comic Dog.

E04

Sixty for Swifty

Mon, Jan 20 2025 3:30 AM GMT+0000 30 min

Julie Bowen; Margaret Cho; Leslie Jones; Carson Kressley; Ross Mathews.

E05

Didn't Work If Nelly Didn't Laugh

Fri, Jan 24 2025 1:00 AM GMT+0000 30 min

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

E06

The Price Was Wrong Drew

Fri, Jan 24 2025 1:30 AM GMT+0000 30 min

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

E07

It's a Hot Gentleman's Sweater

Thu, Jan 30 2025 1:00 AM GMT+0000 30 min

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

E08

They Always Choose Me, Boo!

Thu, Jan 30 2025 1:30 AM GMT+0000 30 min

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

E09

Ex's Get the Square

Thu, Feb 6 2025 1:00 AM GMT+0000 30 min

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

E10

I'm Going to the Wrong Doctor

Thu, Feb 6 2025 1:30 AM GMT+0000 30 min

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

E11

Let's Not Fight In Front of Wiz Khalifa

Thu, Feb 13 2025 1:00 AM GMT+0000 30 min

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

E12

It's a Wooden American

Thu, Feb 13 2025 1:30 AM GMT+0000 30 min

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

E13

A Little Doggy Gave It to Me

Thu, Feb 20 2025 1:00 AM GMT+0000 30 min

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

E14

You Like Granny Panties

Thu, Feb 20 2025 1:30 AM GMT+0000 30 min

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

E15

You Lost Me at Nachos

Thu, Feb 27 2025 3:00 AM GMT+0000 30 min

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

E16

I Can't Find My Wallet

Thu, Feb 27 2025 3:30 AM GMT+0000 30 min

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

E17

That's Dad Math

Sat, May 3 2025 12:00 AM GMT+0000 30 min

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

E18

I'd Lick That Stamp

Sat, May 3 2025 12:30 AM GMT+0000 30 min

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

E19

I've Been in 12 Sandwiches

Sat, May 10 2025 12:00 AM GMT+0000 30 min

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

E20

Between Two Nuts

Sat, May 10 2025 12:30 AM GMT+0000 30 min

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

Season 2

22 episodes

E01

Santa's Got a Little Game

Tue, Dec 23 2025 3:00 AM GMT+0000 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.

E02

Hand This Man a Candy Cane

Tue, Dec 23 2025 3:30 AM GMT+0000 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.

E03

I Will Not Be Ignored, Glenn!

Thu, Jan 8 2026 1:00 AM GMT+0000 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.

E04

Between a Cardigan Sandwich

Thu, Jan 8 2026 1:30 AM GMT+0000 30 min

Celebrity contestants Whitney Cummings, Kat Dennings, Fortune Feimster, Pete Holmes, Tiffany Haddish, Padma Lakshmi, Joel McHale and RuPaul.

E05

This Is the Best Show on TV

Thu, Jan 15 2026 1:00 AM GMT+0000 30 min

Celebrity contestants Whitney Cummings, Ariana Debose, Fortune Feimster, Tiffany Haddish, Arsenio Hall, Lil Rel Howery, Jo Koy and Ms. Pat.

E06

I'm Terrified of Triumph

Thu, Jan 15 2026 1:30 AM GMT+0000 30 min

Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Zarna Garg, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Jay Mohr.

E07

Expect the Unexpected

Thu, Jan 22 2026 1:00 AM GMT+0000 30 min

Celebrity guests Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Julie Chen Moonves, Jason Ritter and Kristen Schaal.

E08

This Always Happens When RuPaul's Around

Thu, Jan 22 2026 1:30 AM GMT+0000 30 min

Celebrity guests Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul.

E09

The Legacy Show

Thu, Jan 29 2026 2:00 AM GMT+0000 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

Thu, Jan 29 2026 2:30 AM GMT+0000 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

Thu, Feb 5 2026 2:00 AM GMT+0000 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

Thu, Feb 5 2026 2:30 AM GMT+0000 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

Mon, Feb 23 2026 1:00 AM GMT+0000 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

Mon, Feb 23 2026 1:00 AM GMT+0000 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

Thu, Mar 12 2026 2:30 AM GMT+0000 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

Thu, Mar 19 2026 2:30 AM GMT+0000 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

Thu, Mar 26 2026 2:30 AM GMT+0000 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

Thu, Apr 9 2026 2:30 AM GMT+0000 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

Thu, Apr 16 2026 2:30 AM GMT+0000 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

Thu, Apr 23 2026 2:30 AM GMT+0000 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

Thu, May 7 2026 2:30 AM GMT+0000 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

Thu, May 28 2026 12:00 AM GMT+0000 30 min

Celebrity contestants Tom Bergeron, Neal Brennan, Whitney Cummings, Ariana Debose, Mark Duplass, Arsenio Hall, Tiffany Haddish and Ms. Pat.

Cast

Nate Burleson as Host

Drew Barrymore as Center Square

Hollywood Squares

Seasons & Episodes

Season 1

Season 2

Cast

User Reviews

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