Bonita Applebum

Released as the second single on 5 July 1990, it began as a demo made in 1985, one of the group's first, and was remade a few years later for the album. Q-Tip first rapped it in a conventional way, but after reading a Miles Davis interview about space, the rests between notes, he changed the beat and adopted a conversational delivery. The song samples RAMP's Daylight, Rotary Connection's Memory Band, Eugene McDaniels's Jagger the Dagger and Little Feat's Fool Yourself. Charles Stone III directed the video. It was one of the first songs recorded for the album.

Pitchfork's Kris Ex wrote that it is still considered one of the best-loved songs hip-hop has produced. Pharrell Williams said he listened to it every day. Its beat was used by B.o.B on Put Me On, and it was sampled for the remix of Monica's So Gone in 2003. Pharrell Williams remixed it for the 2015 anniversary reissue. Rolling Stone listed it among 20 essential songs by the group. It appears in 35 of the 64 logged setlists that list songs, and the earliest show with a logged song list, at The Palace in Los Angeles on 20 April 1990, includes it.