Hollywood Squares (2025)

Season 2

TV-14

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.

Where to Watch Hollywood Squares (2025) • Season 2

22 Episodes

Santa's Got a Little Game
E1
Santa's Got a Little GameAs center square Drew Barrymore and host Nate Burleson bring the holiday cheer, two Christmas-fanatic contestants vying for money and prizes are joined by a roster of celebrity “elves” poised to put the “ho ho ho” in Hollywood, including Tim Meadows, Meghan Trainor, Tichina Arnold, Michelle Buteau, Ana Gasteyer, Thomas Lennon, Bobby Moynihan, Pete Holmes and Triumph the Insult Comic Dog.
Hand This Man a Candy Cane
E2
Hand This Man a Candy CaneThe Christmas festivities continue with guest celebrity “elves” Tim Meadows, Meghan Trainor, Tichina Arnold, Michelle Buteau, Ana Gasteyer, Thomas Lennon, Bobby Moynihan, Pete Holmes and Triumph the Insult Comic Dog.
I Will Not Be Ignored, Glenn!
E3
I Will Not Be Ignored, Glenn!
Between a Cardigan Sandwich
E4
Between a Cardigan SandwichCelebrity Squares include Whitney Cummings, Kat Dennings, Fortune Feimster, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Joel McHale and RuPaul.
This Is the Best Show on TV
E5
This Is the Best Show on TVCelebrity Squares include Whitney Cummings, Ariana Debose, Fortune Feimster, Tiffany Haddish, Arsenio Hall, Lil Rel Howery, Jo Koy and Ms. Pat.
I'm Terrified of Triumph
E6
I'm Terrified of TriumphCelebrity Squares include Anthony Anderson, Glenn Close, Whitney Cummings, Zarna Garg, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Jay Mohr.
Expect the Unexpected
E7
Expect the UnexpectedCelebrity squares include Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Julie Chen Moonves, Jason Ritter and Kristen Schaal.
This Always Happens When RuPaul’s Around
E8
This Always Happens When RuPaul’s AroundCelebrity squares include Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul.
The Legacy Show
E9
The Legacy ShowCelebrity Squares include Tom Bergeron, Whitney Cummings, Tiffany Haddish, Arsenio Hall, Howie Mandel, Thomas Lennon, Leslie Jones and Triumph the Insult Comic Dog.
I Didn’t Know You Were That Flexible
E10
I Didn’t Know You Were That FlexibleCelebrity Squares include Whitney Cummings, Fortune Feimster, Zarna Garg, Tiffany Haddish, Robby Hoffman, Padma Lakshmi, Thomas Lennon, Bill Maher, Joel McHale and Triumph the Insult Comic Dog.
Thicker Than a 1st Grade Pencil
E11
Thicker Than a 1st Grade PencilCelebrity squares include Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer.
I Have a Lot of Exes Watching Right Now
E12
I Have a Lot of Exes Watching Right NowCelebrity squares include Ariana DeBose, Ron Funches, Gabriel “Fluffy” Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash‑Betts, Ms. Pat and Paul Scheer.
A Scream Reunion
E13
A Scream ReunionA Scream reunion occurs when David Arquette joins the panel, alongside fellow Celebrity squares Whitney Cummings, Mark Duplass, Tiffany Haddish, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Thomas Lennon.
I’m Nasty, But I Ain’t No Hero
E14
I’m Nasty, But I Ain’t No HeroCelebrity squares include Whitney Cummings, Ariana Debose, Fortune Feimster, Ryan Fitzpatrick, Tiffany Haddish, Lil Rel Howery, Gabriel Iglesias and Jo Koy.
This Isn’t Survivor
E15
This Isn’t SurvivorCelebrity squares include Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash‑Betts and Ms. Pat.
There’s That Cruella Energy
E16
There’s That Cruella EnergyCelebrity squares Neal Brennan, Glenn Close, Whitney Cummings, Robby Hoffman, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Howie Mandel.
Please Don't Let It Be a Hawk
E17
Please Don't Let It Be a HawkCelebrity Squares: Tichina Arnold, Michelle Buteau, Tony Hawk, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.
90s Fine Baby
E18
90s Fine BabyCelebrity Squares: Tichina Arnold, Michelle Buteau, Method Man, Triumph the Insult Comic Dog, Janelle James, Tig Notaro, Chris Redd and Paul Scheer.
We Have a Lot of SNL Funny in Here Tonight
E19
We Have a Lot of SNL Funny in Here TonightCelebrity Squares: Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Chris Redd, Jason Ritter and Kristen Schaal.
Be Careful What You Ask for Howie
E20
Be Careful What You Ask for HowieCelebrities Whitney Cummings, Mark Duplass, Ana Gasteyer, Tiffany Haddish, Triumph the Insult Comic Dog, Leslie Jones, Thomas Lennon, Howie Mandel and Ross Mathews.
The Wizard of Hollywood Squares
E21
The Wizard of Hollywood SquaresCelebrities Michelle Buteau, Kat Dennings, Tiffany Haddish, Pete Holmes, Thomas Lennon, Bobby Moynihan, Law Roach and Meghan Trainor.
Snooze We Can't Lose
E22
Snooze We Can't LoseCelebrities Tom Bergeron, Neal Brennan, Whitney Cummings, Ariana DeBose, Mark Duplass, Arsenio Hall, Tiffany Haddish and Ms. Pat.