De La Soul's legacy is impressive: The trio essentially invented the alternative hip-hop genre on its first album, 1988's 3 Feet High and Rising, expanding the parameters of rap music's aspirations. Produced by Prince Paul, the album introduced humorous between-song skits, sampled sources as diverse as Serge Gainsbourg and Steely Dan, and featured the unique flows of Plug One (Posdnuos) and Plug Two (Trugoy). Unhappy at being labeled hip-hop hippies, the three declared an end to the "D.A.I.S.Y. Age" on 1991's De La Soul Is Dead while showing a knack for solid songcraft that proved they were no mere fad. "It might blow up, but it won't go pop" became the mantra for 1993's Buhloone Mindstate, an underappreciated gem that nevertheless cracked Billboard's Top 40. Four years later, Stakes Is High ruminated on the sweeping changes befalling hip-hop culture, which had already begun to embrace formulaic thugisms. Another four years passed before Art Official Intelligence: Mosaic Thump again highlighted De La's capacity for reinvention, even if the album was not so much a case of going against the grain as going with the flow. 2001's AOI: Bionix is probably the least inspired effort, but it still held its own against the Ja Rules and Pastor Troys of the world.
The 16 songs on Timeless show a remarkable consistency no other rap act can claim. Though it falls short of being the ultimate De La retrospective, it more than suffices as a greatest-hits album. "Buddy" (featuring the Native Tongues) and "All Good?" (featuring Chaka Khan) come from two entirely different eras, yet both stand as prototypical club anthems. Perhaps the clearest measure of De La's classicism is "Plug Tunin'," its debut single, which wouldn't sound out of place on a contemporary alt-rap label like Def Jux or Stones Throw.