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Hollywood Squares poster

Reality

Hollywood Squares

4.0(7)

First Aired:January 16, 2025

Seasons:2 seasons

Episodes:36

Status:Returning Series

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.

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Cast

Nate Burleson

Nate Burleson

Self - Host

Drew Barrymore

Drew Barrymore

Self

Seasons & Episodes

It's a Dysfunctional Family Show

E1It's a Dysfunctional Family Show

Jan 16, 2025

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

The Mayor of the Sun

E2The Mayor of the Sun

Jan 16, 2025

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

It's a Kiss Party

E3It's a Kiss Party

Jan 19, 2025

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

Sixty for Swifty

E4Sixty for Swifty

Jan 19, 2025

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

Didn't Work If Nelly Didn't Laugh

E5Didn't Work If Nelly Didn't Laugh

Jan 23, 2025

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

The Price Was Wrong Drew

E6The Price Was Wrong Drew

Jan 23, 2025

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

It's a Hot Gentleman's Sweater

E7It's a Hot Gentleman's Sweater

Jan 29, 2025

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

They Always Choose Me, Boo!

E8They Always Choose Me, Boo!

Jan 29, 2025

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

Ex's Get the Square

E9Ex's Get the Square

Feb 5, 2025

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

I'm Going to the Wrong Doctor

E10I'm Going to the Wrong Doctor

Feb 5, 2025

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

Let's Not Fight in Front of Wiz Khalifa

E11Let's Not Fight in Front of Wiz Khalifa

Feb 12, 2025

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

It's a Wooden American

E12It's a Wooden American

Feb 12, 2025

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

A Little Doggy Gave It to Me

E13A Little Doggy Gave It to Me

Feb 19, 2025

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

You Like Granny Panties

E14You Like Granny Panties

Feb 19, 2025

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

You Lost Me at Nachos

E15You Lost Me at Nachos

Feb 26, 2025

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

I Can't Find My Wallet

E16I Can't Find My Wallet

Feb 26, 2025

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

That’s Dad Math

E17That’s Dad Math

May 2, 2025

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

I’d Lick That Stamp

E18I’d Lick That Stamp

May 2, 2025

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

I’ve Been in 12 Sandwiches

E19I’ve Been in 12 Sandwiches

May 9, 2025

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

Between Two Nuts

E20Between Two Nuts

May 9, 2025

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

E1Santa's Got a Little Game

Dec 22, 2025

E2Hand This Man a Candy Cane

Dec 22, 2025

E3I Will Not Be Ignored, Glenn!

Jan 7, 2026

E4Between a Cardigan Sandwich

Jan 7, 2026

E5This Is the Best Show on TV

Jan 14, 2026

E6I'm Terrified of Triumph

Jan 14, 2026

E7Expect the Unexpected

Jan 21, 2026

E8This Always Happens When RuPaul’s Around

Jan 21, 2026

E9The Legacy Show

Jan 28, 2026

E10I Didn’t Know You Were That Flexible

Jan 28, 2026

E11Thicker Than a 1st Grade Pencil

Feb 4, 2026

E12I Have a Lot of Exes Watching Right Now

Feb 4, 2026

E13A Scream Reunion

Feb 22, 2026

E14I’m Nasty, But I Ain’t No Hero

Feb 22, 2026

E15This Isn’t Survivor

Mar 11, 2026

E16There’s That Cruella Energy

Mar 18, 2026

E17Please Don't Let It Be a Hawk

Mar 25, 2026

E1890s Fine Baby

Apr 8, 2026

E19We Have a Lot of SNL Funny in Here Tonight

Apr 15, 2026

E20Be Careful What You Ask for Howie

Apr 22, 2026

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

E21The Wizard of Hollywood Squares

May 6, 2026

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

E22Snooze We Can't Lose

May 27, 2026

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

Storyline

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.

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