Hollywood Squares - Season 2

Hollywood Squares - Season 2

Season 2

Network
DatesDec 22, 2025 - May 6, 2026
Previous Season

Episodes

Santa's Got a Little Game
Season 2Episode 130 min

Santa's Got a Little Game

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.

Dec 22, 2025
Hand This Man a Candy Cane
Season 2Episode 230 min

Hand This Man a Candy Cane

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.

Dec 22, 2025
I Will Not Be Ignored, Glenn!
Season 2Episode 330 min

I Will Not Be Ignored, Glenn!

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

Jan 7, 2026
Between a Cardigan Sandwich
Season 2Episode 430 min

Between a Cardigan Sandwich

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

Jan 7, 2026
This Is the Best Show on TV
Season 2Episode 530 min

This Is the Best Show on TV

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

Jan 14, 2026
I'm Terrified of Triumph
Season 2Episode 630 min

I'm Terrified of Triumph

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

Jan 14, 2026
Expect the Unexpected
Season 2Episode 730 min

Expect the Unexpected

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

Jan 21, 2026
This Always Happens When RuPaul's Around
Season 2Episode 830 min

This Always Happens When RuPaul's Around

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

Jan 21, 2026
The Legacy Show
Season 2Episode 930 min

The Legacy Show

Celebrity guests Tom Bergeron, Whitney Cummings, Tiffany Haddish, Arsenio Hall, Howie Mandel, Thomas Lennon, Leslie Jones and Triumph the Insult Comic Dog.

Jan 28, 2026
I Didn't Know You Were that Flexible
Season 2Episode 1030 min

I Didn't Know You Were that Flexible

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.

Jan 28, 2026
Thicker Than A 1st Grade Pencil
Season 2Episode 1130 min

Thicker Than A 1st Grade Pencil

Celebrity guests Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer.

Feb 4, 2026
I Have a Lot of Exes Watching Right Now
Season 2Episode 1230 min

I Have a Lot of Exes Watching Right Now

Celebrity guests Ariana DeBose, Ron Funches, Gabriel "Fluffy" Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash‑Betts, Ms. Pat and Paul Scheer.

Feb 4, 2026
A Scream Reunion
Season 2Episode 1330 min

A Scream Reunion

Celebrity guests David Arquette, Whitney Cummings, Mark Duplass, Tiffany Haddish, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Thomas Lennon.

Feb 22, 2026
I'm Nasty, But I Ain't No Hero
Season 2Episode 1430 min

I'm Nasty, But I Ain't No Hero

Celebrity guests Whitney Cummings, Ariana Debose, Fortune Feimster, Ryan Fitzpatrick, Tiffany Haddish, Lil Rel Howery, Gabriel Iglesias and Jo Koy.

Feb 22, 2026
This Isn't Survivor
Season 2Episode 1530 min

This Isn't Survivor

Celebrity guests Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash‑Betts and Ms. Pat.

Mar 11, 2026
There's That Cruella Energy
Season 2Episode 1630 min

There's That Cruella Energy

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

Mar 18, 2026
Please Don't Let it Be a Hawk
Season 2Episode 1730 min

Please Don't Let it Be a Hawk

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

Mar 25, 2026
90s Fine Baby
Season 2Episode 1830 min

90s Fine Baby

Celebrity contestants Tichina Arnold, Michelle Buteau, Method Man, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.

Apr 8, 2026
We Have a Lot of SNL Funny in Here Tonight
Season 2Episode 1930 min

We Have a Lot of SNL Funny in Here Tonight

Celebrity contestants Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Chris Redd, Jason Ritter and Kristen Schaal.

Apr 15, 2026
Be Careful What You Ask for Howie
Season 2Episode 2030 min

Be Careful What You Ask for Howie

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

Apr 22, 2026
Snooze We Can't Lose
Season 2Episode 2130 min

Snooze We Can't Lose

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

Apr 29, 2026
The Wizard of Hollywood Squares
Season 2Episode 2230 min

The Wizard of Hollywood Squares

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

May 6, 2026

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