Hollywood Squares - Season 1
1 - It's a Dysfunctional Family Show
Air Date: January 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.
2 - The Mayor of the Sun
Air Date: January 16, 2025
Celebs Drew Barrymore, Drew Carrey, Bobby Moynihan, JB Smoove, Chelsea Peretti, Tichina Arnold, Nicole Byer, Debi Mazar, and Pete Holmes.
3 - It's a Kiss Party
Air Date: January 19, 2025
Celebs Triumph The Insult Comic Dog, Sam Jay, Whitney Cummings, Tyra Banks, Tiffany Haddish, Sheryl Underwood, Thomas Lennon and Drew Barrymore.
4 - Sixty for Swifty
Air Date: January 19, 2025
Celebs Julie Bowen, Margaret Cho, Leslie Jones, Carson Kressley, Ross Mathews, Kevin Nealon, RuPaul and Paul Scheer.
5 - Didn't Work If Nelly Didn't Laugh
Air Date: January 23, 2025
Celebs Chaka Khan, Jay Leno, Tanner Adell, Whitney Cummings, Pete Holmes, Patton Oswalt, Nelly, Thoms Lennon.
6 - The Price Was Wrong Drew
Air Date: January 23, 2025
Celebs Drew Carey, Max Greenfield, Rita Moreno, Bobby Moynihan, Pete Holmes, Lil Rel, Nicole Byer, and Jeff Dunham.
7 - It's a Hot Gentleman's Sweater
Air Date: January 29, 2025
Nicole Byer, Drew Carey, Luenell, Debi Mazar, Bobby Moynihan, Chelsea Peretti, Phil Rosenthal and JB Smoove
8 - They Always Choose Me, Boo!
Air Date: January 29, 2025
Julie Bowen, Margaret Cho, Leslie Jones, Carson Kressley, Jeannie Mai, Kevin Nealon, RuPaul and Paul Scheer
9 - Ex's Get the Square
Air Date: February 5, 2025
Celebrity guests Mayim Bialik, Tiffany Haddish, Pete Holmes, Justin Long, Marsai Martin, Jimmy O. Yang, Kristen Schaal and JB Smoove.
10 - I'm Going to the Wrong Doctor
Air Date: February 5, 2025
Celebrity guests Whitney Cummings, Tiffany Haddish, Kathy Hilton, Triumph the Insult Comic Dog, Thomas Lennon, Ms. Pat, JB Smoove and Casey Wilson.
11 - Let's Not Fight in Front of Wiz Khalifa
Air Date: February 12, 2025
Celebrity guests: Whitney Cummings, Andra Day, Mickey Guyton, Pete Holmes, Wiz Khalifa, Jay Leno, Thomas Lennon and Dionne Warwick.
12 - It's a Wooden American
Air Date: February 12, 2025
Celebrity guests: Tyra Banks, Jeff Dunham, Ron Funches, Tiffany Haddish, Justin Long, Chelsea Peretti, Jay Pharoah and Dusty Slay.
13 - A Little Doggy Gave It to Me
Air Date: February 19, 2025
Celebrity guests: Tichina Arnold, Beth Behrs, Whitney Cummings, Tony Gonzalez, Triumph the Insult Comic Dog, Ross Mathews, Kevin Nealon and Aida Rodriguez.
14 - You Like Granny Panties
Air Date: February 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.
15 - You Lost Me at Nachos
Air Date: February 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.
16 - I Can't Find My Wallet
Air Date: February 26, 2025
Celebrity guests: Tichina Arnold, Mario Cantone, Jo Koy, Loni Love, Melanie Lynskey, Tig Notaro, June Diane Raphael and Jason Ritter.
17 - That’s Dad Math
Air Date: May 2, 2025
Guests include Tichina Arnold, Annaleigh Ashford, Mario Cantone, Jo Koy, Vicky Lawrence, Tig Notaro, Russell Peters and Andrew Rannels.
18 - I’d Lick That Stamp
Air Date: May 2, 2025
Guests include Tiffany Haddish, Justin Long, Marsai Martin, Kevin Nealon, Jimmy O Yang, Dusty Slay, JB Smoove and Casey Wilson.
19 - I’ve Been in 12 Sandwiches
Air Date: May 9, 2025
Celebrity guests include Tichina Arnold, Beth Behrs, Mario Cantone, Pete Holmes, Jo Koy, Tig Notaro, June Diane Raphael, and Kristen Schaal,
20 - Between Two Nuts
Air Date: May 9, 2025
Celebrity guests include Luenell, Debi Mazar, Jack McBrayer, Patton Oswalt, Ravi Patel, Mira Sorvino, Michaela Watkins, and Reggie Watts.