Title(s): Former CEO of Jive Records
Artists They Worked With: Too $hort, Schoolly D, Whodini, A Tribe Called Quest, Boogie Down Productions, E-40

Who the hell is Barry Weiss and why is this old guy the best A&R man in hip-hop history? Answer: He built the most powerful and lasting roster of hip-hop and hip-hop-influenced R&B and pop music in history as the head of Jive Records.

This begs the question: How much credit should the head of a record label get for a career’s worth of signings that often came to his attention via the A&R people who worked for him? For example, it took the late Sean “The Captain” Carasov—a young, wiry British expat on Jive’s staff—to bring A Tribe Called Quest to his attention. What’s more, label heads like Weiss had the best managers and lawyers coming at them all the time with the choice cuts and prime properties. So Weiss had easier access than most to the best of hip-hop culture in the late 80s and early ‘90s.

But Weiss deserves credit because, unlike many of his contemporaries, he nearly always made the right decisions with his artistic judgment and checkbook. You cannot front on the man who invested in the following artists: Whodini. Too Short. Schoolly D. Steady B. Boogie Down Productions and KRS-One. DJ Jazzy Jeff & The Fresh Prince, which launched the career of Will Smith. Souls of Mischief. UGK. Spice One. Keith Murray. R. Kelly. Aaliyah. And in later years, T-Pain and Chris Brown. Weiss’s shrewd but dignified business practices gave E-40, a Bay area artist already making hundreds of thousands of dollars on his own without a label, the incentive to sign with Jive when other bigger labels were clamoring for his business.

(And let’s not forget that Weiss is also responsible for greenlighting a few other projects you might have heard of: The Backstreet Boys. N’Sync and Justin Timberlake. Brittany Spears.)

Extra credit goes to Ann Carli, who’s creative genius for packaging art and soothing sensitive artists was a crucial ingredient in Jive’s early success; and Jeff Sledge, discovered by Stu Fine at Wild Pitch but a longtime member of Jive’s promotion and A&R team.