Hollywood Squares

Hollywood Squares

Continuing First aired 16/Jan/2025 United States English 2 season(s) 42 episode(s)
Reality
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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TimeScore 33% Skip It
Binge Meter 48% Slow Burn
Episode Pulse Quiet 40% activity score
Drop Rate 0% Very Low

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Seasons & Episodes

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Season 2 · Season 2
22 episode(s) · Air date: 22/Dec/2025
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Season Overview

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S2E22
Snooze We Can't Lose
Air date: 27/May/2026 · Time: 20:00 · Runtime: 30 min
Summary

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

Summary

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

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S2E21
The Wizard of Hollywood Squares
Air date: 06/May/2026 · Time: 22:30 · Runtime: 30 min
Summary

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

Summary

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

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S2E20
Be Careful What You Ask for Howie
Air date: 22/Apr/2026 · Time: 22:30 · Runtime: 30 min
Summary

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

Summary

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

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Season 1 · Season 1
20 episode(s) · Air date: 16/Jan/2025
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Season Overview

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S1E20
Between Two Nuts
Air date: 09/May/2025 · Time: 20:30 · Runtime: 22 min
Summary

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

Summary

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

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S1E19
I’ve Been in 12 Sandwiches
Air date: 09/May/2025 · Time: 20:00 · Runtime: 22 min
Summary

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

Summary

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

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S1E17
That’s Dad Math
Air date: 02/May/2025 · Time: 20:00 · Runtime: 22 min
Summary

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

Summary

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

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S1E16
I Can't Find My Wallet
Air date: 26/Feb/2025 · Time: 22:30 · Runtime: 22 min
Summary

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

Summary

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

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S1E15
You Lost Me at Nachos
Air date: 26/Feb/2025 · Time: 22:00 · Runtime: 22 min
Summary

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

Summary

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

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S1E14
You Like Granny Panties
Air date: 19/Feb/2025 · Time: 20:30 · Runtime: 22 min
Summary

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

Summary

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

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S1E13
A Little Doggy Gave It to Me
Air date: 19/Feb/2025 · Time: 20:00 · Runtime: 22 min
Summary

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

Summary

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

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S1E12
It's a Wooden American
Air date: 12/Feb/2025 · Time: 20:30 · Runtime: 22 min
Summary

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

Summary

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

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S1E11
Let's Not Fight in Front of Wiz Khalifa
Air date: 12/Feb/2025 · Time: 20:00 · Runtime: 22 min
Summary

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

Summary

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

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S1E10
I'm Going to the Wrong Doctor
Air date: 05/Feb/2025 · Time: 20:30 · Runtime: 22 min
Summary

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

Summary

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

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S1E9
Ex's Get the Square
Air date: 05/Feb/2025 · Time: 20:00 · Runtime: 22 min
Summary

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

Summary

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

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S1E3
It's a Kiss Party
Air date: 19/Jan/2025 · Time: 22:00 · Runtime: 23 min
Summary

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

Summary

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

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S1E2
The Mayor of the Sun
Air date: 16/Jan/2025 · Time: 20:30 · Runtime: 22 min
Summary

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

Summary

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

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S1E1
It's a Dysfunctional Family Show
Air date: 16/Jan/2025 · Time: 20:00 · Runtime: 22 min
Summary

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

Summary

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

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Cast

Main cast members.

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Nate Burleson
Nate Burleson
Self - Host
Drew Barrymore
Drew Barrymore
Self
Tyra Banks
Tyra Banks
Self
Julie Bowen
Julie Bowen
Self
Whitney Cummings
Whitney Cummings
Self
Tiffany Haddish
Tiffany Haddish
Self
Thomas Lennon
Thomas Lennon
Self
Patricia Williams
Patricia Williams
Self
Tichina Arnold
Tichina Arnold
Self
Nicole Byer
Nicole Byer
Self
Drew Carey
Drew Carey
Self
Pete Holmes
Pete Holmes
Self
Debi Mazar
Debi Mazar
Self
Bobby Moynihan
Bobby Moynihan
Self
Chelsea Peretti
Chelsea Peretti
Self
Jeff Ross
Jeff Ross
Self
Robert Smigel
Robert Smigel
Triumph the Insult Comic Dog (voice)
JB Smoove
JB Smoove
Self

Crew

Creators, directors, writers, and production crew.

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No Photo
Collin L. Howard
Associate Producer
No Photo
Joey Ortega
Consulting Producer
Dionne Harmon
Dionne Harmon
Executive Producer
Drew Barrymore
Drew Barrymore
Executive Producer
No Photo
Elaine Metaxas
Executive Producer
Jesse Collins
Jesse Collins
Executive Producer
Madison Merritt
Madison Merritt
Executive Producer

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