5. Friday (1995)

At the time of its release, Ice Cube was one of the biggest rappers in the world. After finding success with the NWA, he had been a solo artist at the top of his game for six years. During that time Cube started to build a solid filmography but was sick of movies about African Americans portraying the gangster lifestyle. Teaming with DJ Pooh, the two came up with the script for Friday.

Fired from his job and with no prospects, Cube’s Craig Jones decides to spend his Friday hanging out on the porch with his drug-selling best friend Smokey (Chris Rock). When Smokey’s boss demands they pay the $200 Smokey owes him before 10:00 pm that night, the two must do all they can to get the money while encountering a cast of colorful characters. 

Friday turned Cube and Rock into credible actors and established F. Gary Grey (directing his first film) as one to watch in the future. A cult smash, there have been two sequels and an animated series, although none stack up to the original. 

6. Scary Movie (2000)

There are five films in the Scary Movie franchise, and while they are all worth a watch (despite getting progressively worse), you can’t beat the original. Written by the Wayans brothers, Scary Movie is a parody of teen slasher films in the wake of Scream. It borrows from a whole raft of horror films (Halloween, The Blair Witch Project, The Shining, and more) and follows a plot similar to Scream, with a masked killer terrorizing a local town. 

It features an eclectic cast of up and comers (Anna Faris, Regina Hall, and, Lochlyn Munro), wall-to-wall jokes, and the presence of the Wayans brothers (Marlon, Shawn, and Keenan Ivory) in supporting roles. 

7. How High (2001)

Method Man and Redman starring in a film is a sure sign that weed will be involved. In this absurd film, the two rappers play students (despite boh being almost 30) who smoke the ashes of their dead friend. His ghost then appears and helps them pass their entrance exams to Harvard where they get into all sorts of trouble.