Twenty years ago today (October 18), O.C. released his debut album, Word…Life. On the now-defunct-but-legendary Wild Pitch Records, the Organized Konfusion affiliate (who would later become an integral part of Diggin’ In The Crates) made his debut featuring involvement from emerging producer Buckwild, Lord Finesse, Pharoahe Monch and Prince Poetry (Organized Konfusion), and the late DJ Roc Raida.

Although sophomore single “Times Up” would go on to become an bravado-heavy, enduring poster-child of the LP, it was the introspective “Born 2 Live” that set the table. The song would highlight the MC (who claimed both Brooklyn and Queens roots) and his ability to reach the hearts of men (and women) with a slick Rap style, employing ’70s slang, street-savvy tones, and an old soul.

In the years that followed, O would turn down an offer to join Bad Boy Records, where Puff Daddy reportedly wanted to remix Word…Life (which missed the Top 200 charts) by his “Hit-Men,” at Bad Boy who at the time, unofficially included D.I.T.C’s Lord Finesse, Easy Mo Bee, and Pete Rock, among others. Instead, O joined band-mates Showbiz & A.G. at Payday Records, where he released 1997’s Jewelz, which cracked the Top 100 (following a Crooklyn Dodgers appearance). Later on, O would re-join the Wild Pitch family at JCOR for Bon Appetit, before heading to Hieroglyphics’ label, and later on, Mello Music Group.

At the crux of his career, is forever Word…Life, championed by Heads, re-issued twice, and an enduring underground Hip-Hop classic.

Related: A Rare 1994 Remix Surfaces From O.C.’s Word…Life Album By DJ Eclipse (Audio)