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Hip Hop Squares Season 1 Episodes

Season 1 Episode Guide

20 Episodes 2017 -

Episode 1

Tyson Beckford vs. Don Benjamin

Mon, Mar 13, 2017 30 mins

In the series premiere, Tyson Beckford and Don Benjamin answer trivia questions about pop culture. Also: Bobby Brown; T.I.; Keri Hilson; Kelis; Eva Marcille; Faizon Love; Michael Blackson; Tiffany Haddish; and DC Young Fly.

Where to Watch

Episode 2

Ray J vs. Princess Love

Mon, Mar 13, 2017 30 mins

Ray J competes against Princess Love. Also: Ice Cube; T.I.; Adrienne Bailon; Cardi B; Amber Rose; Deon Cole; Affion Crockett; Utkarsh Ambudkar; James Davis.

Where to Watch

Episode 3

Sky vs. Kid Ink

Wed, Mar 15, 2017 30 mins

Sky competes against Kid Ink. Also: Monica; T.I.; Wale; Jasmine "Golden Barbie" Sanders; Selita Ebanks; Rotimi; Deon Cole; Tiffany Haddish; Lil Duval.

Where to Watch

Episode 4

Master P vs. Romeo

Wed, Mar 15, 2017 30 mins

Master P competes against Romeo. Also: O'Shea Jackson Jr.; Teyana Taylor; Tyga; Damien Danté Wayans; Eva Marcille; Jessimae Peluso; Michael Blackson; Tiffany Haddish.

Where to Watch

Episode 5

Stevie J vs. Karlie Redd

Mon, Mar 20, 2017 30 mins

Stevie J; Karlie Redd; T.I.; Yandy Smith; Ray J; Princess Love; Yung Joc.

Where to Watch

Episode 6

Diggy Simmons vs. Vanessa Simmons

Mon, Mar 20, 2017 30 mins

Diggy Simmons; Vanessa Simmons; Teyana Taylor; O'Shea Jackson Jr.; Tyga; Eva Marcille.

Where to Watch

Episode 7

Jessica Dime vs. Jackie Christie

Mon, Mar 27, 2017 30 mins

Jessica Dime; Jackie Christie.

Where to Watch

Episode 8

Kid 'N Play vs. Naughty by Nature

Mon, Mar 27, 2017 30 mins

Kid 'N Play; Naughty by Nature.

Where to Watch

Episode 9

Drita D'Avanzo vs. Joseline Hernandez

Mon, Apr 3, 2017 30 mins

Drita D'Avanzo takes on Joseline Hernandez. Also: Bobby Brown; T.I.; Tyson Beckford; Christina Milian.

Where to Watch

Episode 10

Jessica White vs. Joe Budden

Mon, Apr 3, 2017 30 mins

Jessica White takes on Joe Budden. Also: Ice Cube; T.I.; Adrienne Bailon; Amber Rose.

Where to Watch

Episode 11

Fat Joe vs. French Montana

Mon, Apr 10, 2017 30 mins

Fat Joe takes on French Montana. Also: Nelly; T.I.; Vivica A. Fox; Karrueche.

Where to Watch

Episode 12

BBD vs. SWV

Mon, Apr 10, 2017 30 mins

Bell Biv DeVoe takes on SWV. Also: Michael Ealy; T.I.; Jeannie Mai; Nick and Vanessa Lachey.

Where to Watch

Episode 13

Da Brat vs. LisaRaye

Mon, Sep 25, 2017 30 mins

Mel B; TIP; Nick and Vanessa Lachey; Jeannie Mai; and more.

Where to Watch

Episode 14

Jessie T Usher vs. Lamorne Morris

Mon, Sep 25, 2017 30 mins

O'Shea Jackson Jr.; TIP; T-Pain; Vanessa Simmons; and more.

Where to Watch

Episode 15

Jazmyn Simon vs. LeToya Luckett

Mon, Sep 25, 2017 30 mins

Bobby Brown; TIP; Tyson Beckford; Christina Milian; and more.

Where to Watch

Episode 16

Sevyn Streeter vs. Justin Combs

Mon, Oct 2, 2017 30 mins

A hip-hop party featuring artists O'Shea Jackson Jr., Teyana Taylor, Tyga, Eva Marcille, and more.

Where to Watch

Episode 17

Trina vs. Dreezy

Mon, Oct 2, 2017 30 mins

Ice Cube; TIP; Adrienne Bailon; Amber Rose; and more.

Where to Watch

Episode 18

Demetrius Shipp Jr. vs. Machine Gun Kelly

Mon, Oct 2, 2017 30 mins

Cedric the Entertainer; TIP; Michael Ealy; Nick and Vanessa Lachey; and more.

Where to Watch

Episode 19

Kent Jones vs. Nick Young

Mon, Oct 9, 2017 30 mins

Mike Epps; TIP; O'Shea Jackson Jr.; T-Pain; Tisha Campbell-Martin; and more.

Where to Watch

Episode 20

DJ Drama vs. Jessica Burciaga

Mon, Oct 9, 2017 30 mins

TIP; Wale; Selita Ebanks; Rotimi; Deon Cole; and more.

Where to Watch