De La Soul formed while the trio -- Posdnous (born Kelvin Mercer, August 17, 1969), Trugoy the Dove (b. David Jude Joliceur, September 21, 1968), Pasemaster Mase (b. Vincent Mason, March 27, 1970) -- were attending high school in the late '80s. The stage names of all of the members derived from in-jokes: Posdnous was an inversion of Mercer's DJ name, Sound-Sop; Trugoy was an inversion of Joliceur's favorite food, yogurt. De La Soul's demo tape, "Plug Tunin'," came to the attention of Prince Paul, the leader and producer of the New York rap outfit, Stetsasonic. Prince Paul played the tape to several colleagues and helped the trio land a contract with Tommy Boy Records.

Prince Paul produced De La Soul's debut album, 3 Feet High and Rising, which was released in the spring of 1989. Several critics and observers labeled the group as a neo-hippie band, because the record praised peace and love, as well as proclaiming that this was the dawning of "the D.A.I.S.Y. age" (Da Inner Sound, Y'all). Though the trio was uncomfortable with the hippie label, there was no denying that the humor and eclecticism presented an alternative to the hardcore rap that dominated hip-hop. De La Soul quickly were perceived as the leaders of a contigent of New York-based alternative rappers which also included A Tribe Called Quest, Queen Latifah, the Jungle Brothers and Monie Love; all of these artists dubbed themselves the Native Tongues Posse.

For a while, it looked as if De La Soul and the Native Tongues Posse would eclipse hardcore hip-hop in terms of popularity. "Me Myself and I" became a Top 40 pop hit in the U.S. (number one R&B), while the album reached number 24 (number one R&B) and went gold. At the end of the year, 3 Feet High and Rising topped many best-of-the-year lists, including The Village Voice. With all of the acclaim came some unwanted attention, most notably in the form of a lawsuit by the Turtles. De La Soul had sampled the Turtles' "You Showed Me" and layered it with a French lesson on a track on 3 Feet High called "Transmitting Live from Mars," without getting the permission of the '60s pop group. The Turtles won the case and the decision not only had substantial impact on De La Soul, but on rap in general. Following the suit, all samples had to be legally cleared before an album could be released. Not only did this have the end result of rap reverting back to instrumentation, thereby altering how the artists worked, it also meant that several albums in the pipeline had to be delayed in order for samples to clear. One of those albums was De La Soul's second album, De La Soul is Dead.