1. You Look Like A Descendant of Frederick Douglass

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. 17 October 2023. 22 min

The Sleepy Clubber takes on the Temptations Look-alike. Tiffany Haddish is center square. In this episode Tiffany Haddish flirts with Christian Keyes, Amanda Seales takes a stand and Loni Love twerks for Big Freedia.

2. The Hood Therapist vs. The Hoochie Historian

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. 17 October 2023. 22 min

The Hood Therapist takes on the Hoochie Historian as center square Kirk Franklin leads a congregation of stars including Tisha Campbell, Amin Joseph, Affion Crockett and more.

3. Ooh... I Need a Napkin

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. 24 October 2023. 22 min

The Fashionable Weapons Specialist takes on the Well-Rounded Veterans Affairs Rep as center square Taye Diggs leads a team of stars that includes Kym Whitley, Safaree and Karrueche Tran.

4. Ain't Nothing Like a Sugar Momma

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. 24 October 2023. 22 min

The Cosmetologist of the Ball takes on the Lit Godsister in this star-studded game with Tisha Campbell as the center square, plus Ray J, Taye Diggs, Luenell and more hilarious celebs

7. Can’t Have No Cold Hot Sauce

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. 7 November 2023. 22 min

The Nurse with Game faces off against The Hype Teacher with Bobby Brown as center square, plus Kel Mitchell, Amanda Seales and other celebs talk hot sauce, proper pronunciation and more.

8. He Need a Girl Who Don’t Take Baths

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. 14 November 2023. 22 min

It’s The Sneaker Fiend versus The Gamma Blue Fanatic with Bresha Webb sitting in the center square, and Affion Crockett, B. Simone and other famous faces get spiritual.

9. The Musical Chameleon vs. The Singing Admin Assistant

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. 21 November 2023. 22 min

The Musical Chameleon takes on The Singing Admin Assistant; Deon Cole is center square.

10. All My Life I Had to Church

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. 28 November 2023. 22 min

A new take on the classic Hollywood Squares game show is headed to VH1. The network has teamed with Jesse Collins Entertainment and Kevin Hart‘s Hartbeat on Celebrity Squares, a modern twist on the classic format featuring Black pop culture trivia.

11. Episode 11

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. 28 November 2023. 22 min

A new take on the classic Hollywood Squares game show is headed to VH1. The network has teamed with Jesse Collins Entertainment and Kevin Hart‘s Hartbeat on Celebrity Squares, a modern twist on the classic format featuring Black pop culture trivia.