Hip Hop Squares is an American television game show originally hosted by Peter Rosenberg, which debuted on MTV2 on May 22, 2012. The show is a licensed format of CBS Television Distribution's Hollywood Squares (King World Productions, CBS Television Distribution's predecessor company, acquired the franchise in 1991 from Orion Television) featuring mostly rappers. The MTV2 version of the show was taped in Brooklyn, New York. The VH1 version was taped in Hollywood, California.

Because of the show's status as part of the Hollywood Squares franchise, the show marked the sixth decade that a version of the franchise has aired on television, joining Let's Make a Deal, Jeopardy!, and The Newlywed Game (later joined by Wheel of Fortune and Family Feud) as a game show that has aired in six different decades. (Only The Price Is Right and To Tell the Truth have been on longer; both have aired in eight decades.)

On July 28, 2016, VH1 announced a new version of Hip Hop Squares, which premiered on March 13, 2017. The series is executive produced by rapper and actor Ice Cube and hosted by DeRay Davis. Additionally, Davis was a semi-regular panelist on the original MTV2 version before becoming the host of the VH1 version. A fourth season (second for VH1) began on April 18, 2018. The fifth season (third for VH1) premiered on August 13, 2019.