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The Best Episodes of Hollywood Squares Season 1

Every episode of Hollywood Squares Season 1 ranked from best to worst. Discover the Best Episodes of Hollywood Squares Season 1!

The Best Episodes of Hollywood Squares Season 1

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...
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  1. Background image for It's a Dysfunctional Family Show
    5.9/10(38 votes)

    #1 - 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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  2. Background image for The Mayor of the Sun
    6.1/10(29 votes)

    #2 - 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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  3. Background image for It's a Kiss Party
    6.0/10(25 votes)

    #3 - 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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  4. Background image for Sixty for Swifty
    6.7/10(25 votes)

    #4 - 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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  5. Background image for Didn't Work If Nelly Didn't Laugh
    6.8/10(18 votes)

    #5 - 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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  6. Background image for The Price Was Wrong Drew
    6.9/10(18 votes)

    #6 - 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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    7. Trending NowTRENDING NOW

    The 20 BEST Episodes of Hollywood Squares

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  7. Background image for It's a Hot Gentleman's Sweater
    7.1/10(18 votes)

    #7 - 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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  8. Background image for They Always Choose Me, Boo!
    7.4/10(17 votes)

    #8 - 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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  9. Background image for Ex's Get the Square
    7.8/10(20 votes)

    #9 - 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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  10. Background image for I'm Going to the Wrong Doctor
    7.2/10(19 votes)

    #10 - 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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  11. Background image for Let's Not Fight in Front of Wiz Khalifa
    7.2/10(18 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. Background image for It's a Wooden American
    7.1/10(18 votes)

    #12 - 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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  13. Background image for A Little Doggy Gave It to Me
    7.8/10(13 votes)

    #13 - 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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  14. Background image for You Like Granny Panties
    7.2/10(13 votes)

    #14 - 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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  15. Background image for You Lost Me at Nachos
    7.4/10(14 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. Background image for I Can't Find My Wallet
    7.4/10(14 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. Background image for That’s Dad Math
    7.5/10(9 votes)

    #17 - 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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  18. Background image for I’d Lick That Stamp
    7.5/10(10 votes)

    #18 - 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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  19. Background image for I’ve Been in 12 Sandwiches
    7.8/10(8 votes)

    #19 - 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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  20. Background image for Between Two Nuts
    7.6/10(10 votes)

    #20 - 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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Season 1 Ratings Summary

"It's a Dysfunctional Family Show" is the best rated episode of "Hollywood Squares" season 1. It scored 5.9/10 based on 38 votes. Directed by Unknown and written by Unknown, it aired on 1/16/2025. This episode is rated 0.2 points higher than the second-best, "The Mayor of the Sun".