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The Best Episodes of Hollywood Squares

Every episode of Hollywood Squares ranked from best to worst. Let's dive into the Best Episodes of Hollywood Squares!

Binge this in 7h 21m•Peaking at 8.4/10

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

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Episode Rankings

  1. #1 Fan Favorite
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    Hollywood Squares Season 2 Episode 6 - I'm Terrified of Triumph
    8.4/10(8 votes)

    #1 - I'm Terrified of Triumph

    S2:E6

    No description available

    Director:Unknown
    Writer:Unknown

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  2. Hollywood Squares Season 2 Episode 4 - Between a Cardigan Sandwich
    8.3/10(7 votes)

    #2 - Between a Cardigan Sandwich

    S2:E4

    No description available

    Director:Unknown
    Writer:Unknown

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  3. Hollywood Squares Season 1 Episode 20 - Between Two Nuts
    8.1/10(13 votes)

    #3 - Between Two Nuts

    S1:E20

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

    Director:Unknown
    Writer:Unknown

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  4. Hollywood Squares Season 2 Episode 8 - This Always Happens When RuPaul’s Around
    7.8/10(6 votes)

    #4 - This Always Happens When RuPaul’s Around

    S2:E8

    No description available

    Director:Unknown
    Writer:Unknown

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  5. Hollywood Squares Season 1 Episode 9 - Ex's Get the Square
    7.7/10(23 votes)

    #5 - Ex's Get the Square

    S1:E9

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

    Director:Unknown
    Writer:Unknown

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  6. Hollywood Squares Season 1 Episode 19 - I’ve Been in 12 Sandwiches
    7.7/10(12 votes)

    #6 - I’ve Been in 12 Sandwiches

    S1:E19

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

    Director:Unknown
    Writer:Unknown

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    7. Trending NowTRENDING NOW

    The 20 WORST Episodes of Hollywood Squares

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  7. Hollywood Squares Season 2 Episode 5 - This Is the Best Show on TV
    7.7/10(8 votes)

    #7 - This Is the Best Show on TV

    S2:E5

    No description available

    Director:Unknown
    Writer:Unknown

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  8. Hollywood Squares Season 1 Episode 13 - A Little Doggy Gave It to Me
    7.6/10(18 votes)

    #8 - A Little Doggy Gave It to Me

    S1:E13

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

    Director:Unknown
    Writer:Unknown

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  9. Hollywood Squares Season 1 Episode 18 - I’d Lick That Stamp
    7.6/10(15 votes)

    #9 - I’d Lick That Stamp

    S1:E18

    Guests include Tiffany Haddish, Justin Long, Marsai Martin, Kevin Nealon, Jimmy O Yang, Dusty Slay, JB Smoove and Casey Wilson.

    Director:Unknown
    Writer:Unknown

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  10. Hollywood Squares Season 2 Episode 7 - Expect the Unexpected
    7.6/10(6 votes)

    #10 - Expect the Unexpected

    S2:E7

    No description available

    Director:Unknown
    Writer:Unknown

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  11. Hollywood Squares Season 1 Episode 11 - Let's Not Fight in Front of Wiz Khalifa
    7.5/10(20 votes)

    #11 - Let's Not Fight in Front of Wiz Khalifa

    S1:E11

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

    Director:Unknown
    Writer:Unknown

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  12. Hollywood Squares Season 1 Episode 17 - That’s Dad Math
    7.5/10(13 votes)

    #12 - That’s Dad Math

    S1:E17

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

    Director:Unknown
    Writer:Unknown

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  13. Hollywood Squares Season 1 Episode 10 - I'm Going to the Wrong Doctor
    7.4/10(21 votes)

    #13 - I'm Going to the Wrong Doctor

    S1:E10

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

    Director:Unknown
    Writer:Unknown

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  14. Hollywood Squares Season 1 Episode 12 - It's a Wooden American
    7.4/10(20 votes)

    #14 - It's a Wooden American

    S1:E12

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

    Director:Unknown
    Writer:Unknown

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  15. Hollywood Squares Season 1 Episode 15 - You Lost Me at Nachos
    7.4/10(18 votes)

    #15 - You Lost Me at Nachos

    S1:E15

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

    Director:Unknown
    Writer:Unknown

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  16. Hollywood Squares Season 1 Episode 16 - I Can't Find My Wallet
    7.4/10(18 votes)

    #16 - I Can't Find My Wallet

    S1:E16

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

    Director:Unknown
    Writer:Unknown

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  17. Hollywood Squares Season 1 Episode 14 - You Like Granny Panties
    7.3/10(17 votes)

    #17 - You Like Granny Panties

    S1:E14

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

    Director:Unknown
    Writer:Unknown

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  18. Hollywood Squares Season 2 Episode 1 - Santa's Got a Little Game
    7.3/10(10 votes)

    #18 - Santa's Got a Little Game

    S2:E1

    No description available

    Director:Unknown
    Writer:Unknown

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  19. Hollywood Squares Season 1 Episode 5 - Didn't Work If Nelly Didn't Laugh
    7.2/10(21 votes)

    #19 - Didn't Work If Nelly Didn't Laugh

    S1:E5

    Celebs Chaka Khan, Jay Leno, Tanner Adell, Whitney Cummings, Pete Holmes, Patton Oswalt, Nelly, Thoms Lennon.

    Director:Unknown
    Writer:Unknown

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  20. Hollywood Squares Season 1 Episode 8 - They Always Choose Me, Boo!
    7.2/10(23 votes)

    #20 - They Always Choose Me, Boo!

    S1:E8

    Julie Bowen, Margaret Cho, Leslie Jones, Carson Kressley, Jeannie Mai, Kevin Nealon, RuPaul and Paul Scheer

    Director:Unknown
    Writer:Unknown

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  21. Hollywood Squares Season 1 Episode 7 - It's a Hot Gentleman's Sweater
    7.1/10(23 votes)

    #21 - It's a Hot Gentleman's Sweater

    S1:E7

    Nicole Byer, Drew Carey, Luenell, Debi Mazar, Bobby Moynihan, Chelsea Peretti, Phil Rosenthal and JB Smoove

    Director:Unknown
    Writer:Unknown

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  22. Hollywood Squares Season 1 Episode 6 - The Price Was Wrong Drew
    7.0/10(23 votes)

    #22 - The Price Was Wrong Drew

    S1:E6

    Celebs Drew Carey, Max Greenfield, Rita Moreno, Bobby Moynihan, Pete Holmes, Lil Rel, Nicole Byer, and Jeff Dunham.

    Director:Unknown
    Writer:Unknown

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  23. Hollywood Squares Season 2 Episode 2 - Hand This Man a Candy Cane
    6.8/10(10 votes)

    #23 - Hand This Man a Candy Cane

    S2:E2

    No description available

    Director:Unknown
    Writer:Unknown

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  24. Hollywood Squares Season 1 Episode 4 - Sixty for Swifty
    6.7/10(29 votes)

    #24 - Sixty for Swifty

    S1:E4

    Celebs Julie Bowen, Margaret Cho, Leslie Jones, Carson Kressley, Ross Mathews, Kevin Nealon, RuPaul and Paul Scheer.

    Director:Unknown
    Writer:Unknown

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  25. Hollywood Squares Season 1 Episode 2 - The Mayor of the Sun
    6.3/10(33 votes)

    #25 - The Mayor of the Sun

    S1:E2

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

    Director:Unknown
    Writer:Unknown

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Best Episodes Summary

"I'm Terrified of Triumph" is the best rated episode of "Hollywood Squares". It scored 8.4/10 based on 8 votes. Directed by Unknown and written by Unknown, it aired on 1/14/2026. This episode scored 0.1 points higher than the second highest rated, "Between a Cardigan Sandwich".