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The Worst Episodes of Hollywood Squares

Every episode of Hollywood Squares ranked from worst to best. Explore the Worst 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 Worst Episode
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    Hollywood Squares Season 2 Episode 9 - The Legacy Show
    0.0/10(0 votes)

    #1 - The Legacy Show

    S2:E9

    No description available

    Director:Unknown
    Writer:Unknown

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  2. Hollywood Squares Season 2 Episode 10 - I Didn’t Know You Were That Flexible
    0.0/10(0 votes)

    #2 - I Didn’t Know You Were That Flexible

    S2:E10

    No description available

    Director:Unknown
    Writer:Unknown

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  3. Hollywood Squares Season 2 Episode 11 - Thicker Than a 1st Grade Pencil
    0.0/10(0 votes)

    #3 - Thicker Than a 1st Grade Pencil

    S2:E11

    No description available

    Director:Unknown
    Writer:Unknown

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  4. Hollywood Squares Season 2 Episode 12 - I Have a Lot of Exes Watching Right Now
    0.0/10(0 votes)

    #4 - I Have a Lot of Exes Watching Right Now

    S2:E12

    No description available

    Director:Unknown
    Writer:Unknown

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  5. Hollywood Squares Season 2 Episode 3 - Will Not Be Ignored, Glenn!
    5.5/10(2 votes)

    #5 - Will Not Be Ignored, Glenn!

    S2:E3

    No description available

    Director:Unknown
    Writer:Unknown

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  6. Hollywood Squares Season 1 Episode 3 - It's a Kiss Party
    6.0/10(28 votes)

    #6 - It's a Kiss Party

    S1:E3

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

    Director:Unknown
    Writer:Unknown

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  7. Hollywood Squares Season 1 Episode 1 - It's a Dysfunctional Family Show
    6.1/10(41 votes)

    #7 - It's a Dysfunctional Family Show

    S1:E1

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

    Director:Unknown
    Writer:Unknown

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

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

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

    #10 - Hand This Man a Candy Cane

    S2:E2

    No description available

    Director:Unknown
    Writer:Unknown

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

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

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

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

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

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

    #16 - Santa's Got a Little Game

    S2:E1

    No description available

    Director:Unknown
    Writer:Unknown

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

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

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

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

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

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

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

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

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

    #25 - Expect the Unexpected

    S2:E7

    No description available

    Director:Unknown
    Writer:Unknown

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Worst Episodes Summary

"The Legacy Show" is the worst rated episode of "Hollywood Squares". It scored /10 based on 0 votes. Directed by Unknown and written by Unknown, it aired on 1/28/2026. This episode scored 0.0 points lower than the second lowest rated, "I Didn’t Know You Were That Flexible".