Jay Z’s Reasonable Doubt has been described as one of hip-hop's most mature debut albums ever. If the Brooklyn upstart already sounded like a sage veteran on his '96 opening statement, that’s because, well, he kind of was one. He had already been recording for a full decade.

The man born Shawn Carter was just 16 in 1986, when High Potent, the Brooklyn crew he'd joined under his mentor Jaz-O, released its lone single "H.P. Gets Busy." Jay would go on to play sideman for Jaz on his fellow Marcy Houses native's solo singles “Hawaiian Sophie” (1989) and “The Originators” (1990), before making cameos on records by Big Daddy Kane, Big L and Original Flavor.

While Jay officially only released one single—“In My Lifetime”—prior to Reasonable Doubt, some fascinating demo recordings from this period have emerged via mixtapes and the Internet over the years, offering a peek at his growth from gimmicky rapid-fire rhymer to the sophisticated don of Reasonable Doubt. Though spotty in terms of audio quality and dated, occasionally, by Jay's propensity for double-time flows, this material combined with some of Jigga's more choice cameos represents at least an album's worth of notable, yet mostly little-known, pre-Reasonable Doubt material.

Here's a look at Jay Z's Best Songs Before "Reasonable Doubt"

Written by Jesse Serwer (@JesseSerwer)

RELATED: 20 Underrated Jay-Z Songs
RELATED: 50 Things You Didn't Know About Jay-Z
RELATED: The 100 Best Jay-Z Songs