Plot Synopsis

Hosted by comedian DeRay Davis and executive produced by Ice Cube, HIP HOP SQUARES is VH1's version of the classic game show, HOLLYWOOD SQUARES. Featuring the biggest names in hip hop, comedy and entertainment as they come to play and stay to party, celebrity contestants match wits and test their pop culture knowledge with the superstar squares by playing "tic-tac-doe for dough" for one lucky fan. The celebs don't necessarily know all the answers, but they can be convincing enough to fool the contestants and have a really great time in the process. Celebrity contestants and squares include: Ice Cube; Teyana Taylor; T.I.P.; Amber Rose; Fat Joe; Remy Ma; French Montana; Mel B; Nelly; Karrueche; O'Shea Jackson Jr.; Tyga; T-Pain; Master P; Monica; Cedric the Entertainer; Keri Hilson; THE REAL's Adrienne Bailon and Jeannie Mai; Bobby Brown; Bell Biv DeVoe and THE NEW EDITION STORY's Faizon Love and Woody McClain; Jackie Christie from BASKETBALL WIVES: LA; LOVE & HIP HOP: ATLANTA's Joseline Hernandez, Jessica Dime, Karlie Redd, Mimi Faust and Yung Joc; LOVE & HIP HOP: NEW YORK's Cardi B and Yandy Smith; LOVE & HIP HOP: HOLLYWOOD's Princess Love, Ray J, Fizz and Safaree Samuels; MOB WIVES' Drita D'Avanzo; BLACK INK CREW's Sky; and Stevie J from LEAVE IT TO STEVIE. Additional celebrity guests include (in alphabetical order by first name): Affion Crockett; Alesha Renee; Christina Milian; Da Brat; Damien Dante Wayans; DC Young Fly; Deon Cole; Demetrius Shipp Jr.; Diggy Simmons; DJ Drama; DJ Yella; Don Benjamin; Dreezy; Erica Ash; Eva Marcille; James Davis; Jasmine 'Golden Barbie' Sanders; Jazmyn Simon; Jessica Burciaga; Jessica White; Jessimae Peluso; Jessie T Usher; Joe Budden; Justin Combs; Kelis; Kent Jones; Kid 'N Play; Kid Ink; Lamorne Morris; Letoya Luckett; Lil Duval; LisaRaye McCoy; Machine Gun Kelly; Michael Blackson; Michael Ealy; Mike Epps; Naughty By Nature; Nick & Vanessa Lachey; Nick Young; Romeo; Rotimi; Selita Ebanks; Sevyn Streeter; R&B group SWV; Tiffany Haddish; Tisha Campbell-Martin; Too Short; T-Pain; Trina; Tyson Beckford; Utkarsh Ambudkar; Vanessa Simmons; Vivica A. Fox; and Wale.

The sophomore season of HIP HOP SQUARES premiered on Wednesday, April 18, 2018 from 10-11pm ET/PT, as VH1 debuted back-to-back new episodes. After a one-month break, HIP HOP SQUARES returned with new episodes on Wednesday, June 20, 2018 from 9-10pm ET/PT, as VH1 debuted back-to-back new episodes.

Season 3 of HIP HOP SQUARES premiered on Tuesday, August 13, 2019 from 8-9pm ET/PT, as VH1 debuted back-to-back new episodes: "Blueface vs. Dream Doll" (Amanda Seales; Tip; Safaree; Erica Mena; K. Michelle; Saweetie) and "Queen Naija vs. Clarence White" (NeNe Leakes; O'Shea Jackson Jr.; Ray J; Bresha Webb; Justina Valentine). For the rest of the season, additional celebrity guests include: Ice Cube; DC Young Fly; B. Simone; Pretty Vee; Rick Ross; Tamar Braxton; Eva Marcille; Jordyn Woods; Lil Duval; Deon Cole; Jackie Christie; Pretty Vee; and more.
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On Tuesday, September 17, 2019 at 8pm ET/PT VH1 premiered "Shekinah Anderson vs. Kash Doll," the season finale of HIP HOP SQUARES, featuring Tamar Braxton, Tip, Ray J, Jasmine Sanders, Jordyn Woods and more.