During the scene on the subway when Andre is listing his favorite comedians, Chelsea asks him about Charlie Chaplin and he praises Chaplin, saying that he basically invented comedy. Later in the film, DMX sings a rendition of the song "Smile", which was co-written by Chaplin.
The film was inspired by Kevin Smith's relationship with former journalist Jennifer Schwalbach Smith. Chris Rock said: "Kevin Smith, who's a friend of mine, married a journalist. And there's something cute and romantic about that. So the idea for Top Five was in my head for a while: a day in the life of a movie star, getting interviewed, falling for a girl he's only met that day. I just didn't have the balls to write it. Finally I got a little courage and went for it."
In one scene, Andre (Chris Rock) is wearing a Red Hot Chili Peppers t-shirt. Chris is a well known fan and friend of the band. He even directed the band's 2006 music video for their song "Hump de Bump". Andre later mentions the band in sexual context.
Chris Rock on how his friend Louis C.K. encouraged him to write the script: "He told me to just go in a room and write and not show it to anyone."