Before Jay-Z fashioned himself into hip-hop’s most notorious capitalist, he was a street hustler from the projects who rapped about what he knew — and was very, very good at it. Skeptics who’ve never cared for Jigga’s crossover efforts should turn to his debut, Reasonable Doubt, as the deserving source of his legend. Reasonable Doubt is often compared to another New York landmark, Nas’ Illmatic: A hungry young MC with a substantial underground buzz drops an instant classic of a debut, detailing his experiences on the streets with disarming honesty, and writing some of the most acrobatic rhymes heard in quite some time. (Plus, neither artist has since approached the street cred of his debut, The Blueprint notwithstanding.) Parts of the persona that Jay-Z would ride to superstardom are already in place: He’s cocky bordering on arrogant, but playful and witty, and exudes an effortless, unaffected cool throughout. And even if he’s rapping about rising to the top instead of being there, his material obsessions are already apparent. Jay-Z the hustler isn’t too different from Jay-Z the rapper: Hustling is about living the high life and getting everything you can, not violence or tortured glamour or cheap thrills. In that sense, the album’s defining cut might not be one of the better-known singles — “Can’t Knock the Hustle,” “Dead Presidents II,” “Feelin’ It,” or the Foxy Brown duet, “Ain’t No Nigga.” It just might be the brief “22 Two’s,” which not only demonstrates Jay-Z’s extraordinary talent as a pure freestyle rapper, but also preaches a subtle message through its club hostess: Bad behavior gets in the way of making money. Perhaps that’s why Jay-Z waxes reflective, not enthusiastic, about the darker side of the streets; songs like “D’Evils” and “Regrets” are some of the most personal and philosophical he’s ever recorded. It’s that depth that helps Reasonable Doubt rank as one of the finest albums of New York’s hip-hop renaissance of the ’90s. – Steve Huey