Every season of Hip Hop Squares ever, ranked from best to worst by thousands of votes from fans of the show. The best seasons of Hip Hop Squares!

Bobby Brown; Tip; Keri Hilson; Kelis; Eva Marcille; Faizon Love; Michael Blackson; Tiffany Haddish; DC Young Fly

Tyson Beckford vs. Don Benjamin

Come to Play. Stay to Party. With Ice Cube, TIP, Adrienne Bailon, Cardi B and more.

Ray J vs. Princess Love

Come to Play. Stay to Party. With Monica, TIP, Wale, Selita Ebanks and more.

Sky vs. Kid Ink

Come to Play. Stay to Party. With O'Shea Jackson Jr., Teyana Taylor, Tyga, Eva Marcille and more.

Master P vs. Romeo

A fun, interactive, high stakes battle of pop culture and a lively new take on the classic Hollywood game show format. Celebrity contestants face off and play "tic-tac-toe for dough”, all for a lucky fan. Hosted by DeRay Davis.

Stevie J vs. Karlie Redd

Diggy Simmons vs. Vanessa Simmons

Come to Play. Stay to Party. With O'Shea Jackson Jr., TIP, T-Pain, Tisha Martin-Campbell and more.

Jessica Dime vs. Jackie Christie

Come to Play. Stay to Party. With Fat Joe, TIP, Karrueche, Vivica A. Fox and more.

Kid ‘N Play vs. Naughty By Nature

Come to Play. Stay to Party. With Bobby Brown, TIP, Tyson Beckford, Christina Milian and more.

Drita D'Avanzo vs. Joseline Hernandez

Come to Play. Stay to Party. With Ice Cube, TIP, Adrienne Bailon, Amber Rose and more.

Jessica White vs. Joe Budden

Come to Play. Stay to Party. With Nelly, TIP, Vivica A. Fox, Karrueche and more.

Episode 11

Episode 4

Episode 5

Episode 6

Celebrity contestants face off and play "tic-tac-toe for dough", all for a 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.

The Best Seasons of Hip Hop Squares

The Best Seasons of Hip Hop Squares

Season 1

Season 2