Hollywood Squares Season 2 Episodes

Episode 1

Santa's Got a Little Game

Sun, Dec 21, 2025

Celebrity contestants Tim Meadows, Meghan Trainor, Tichina Arnold, Michelle Buteau, Ana Gasteyer, Thomas Lennon, Bobby Moynihan, Pete Holmes and Triumph the Insult Comic Dog.

Episode 2

Hand This Man a Candy Cane

Sun, Dec 21, 2025

Celebrity contestants Tim Meadows, Meghan Trainor, Tichina Arnold, Michelle Buteau, Ana Gasteyer, Thomas Lennon, Bobby Moynihan, Pete Holmes and Triumph the Insult Comic Dog.

Episode 3

I Will Not Be Ignored, Glenn!

Wed, Jan 7, 202630 mins

Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Pete Holmes, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Ross Mathews.

Episode 4

Between a Cardigan Sandwich

Wed, Jan 7, 2026

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

Episode 5

This Is the Best Show on TV

Wed, Jan 14, 202630 mins

Episode 6

I'm Terrified of Triumph

Wed, Jan 14, 202630 mins

Episode 7

Expect the Unexpected

Wed, Jan 21, 202630 mins

Episode 8

This Always Happens When RuPaul's Around

Wed, Jan 21, 202630 mins

Episode 9

The Legacy Show

Wed, Jan 28, 202630 mins

Episode 10

I Didn't Know You Were that Flexible

Wed, Jan 28, 202630 mins

Episode 11

Thicker Than a 1st Grade Pencil

Wed, Feb 4, 202630 mins

Celebrity Squares: Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer. Contestants: Jake from Los Angeles, Calif., and Moni from Montgomery, Ala.

Episode 12

I Have a Lot of Exes Watching Right Now

Wed, Feb 4, 202630 mins

Celebrity Squares: Ariana DeBose, Ron Funches, Gabriel "Fluffy" Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash Betts, Ms. Pat and Paul Scheer. Contestants: Johnnie from Ft. Pierce, Fla., and Casey from San Diego, Calif.

Episode 13

A Scream Reunion

Wed, Mar 11, 2026

Celebrity Squares: Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash Betts and Ms. Pat. Contestants: Jared from Marlton, N.J., and Danielle from West Hills, Calif.

Episode 16

There's That Cruella Energy

Wed, Mar 18, 202630 mins

Celebrity guests Neal Brennan, Glenn Close, Whitney Cummings, Robby Hoffman, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones, and Howie Mandel;

Episode 17

Please Don't Let It Be a Hawk

Wed, Mar 25, 202630 mins

Celebrities Tichina Arnold, Michelle Buteau, Tony Hawk, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd, and Paul Scheer;

Episode 18

90s Fine Baby

Wed, Apr 8, 202630 mins

Celebrities Tichina Arnold, Michelle Buteau, Method Man, Triumph the Insult Dog, Janelle James, Tig Notaro, Chris Redd, and Paul Scheer;

Episode 19

We Have a Lot of SNL Funny in Here Tonight

Wed, Apr 15, 202630 mins

Celebrities Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Chris Redd, Jason Ritter, and Kristen Schaal;

Episode 20

Be Careful What You Ask for Howie

Wed, Apr 22, 202630 mins

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