Heavy D. has managed perhaps the ultimate balancing act. He's remained a positive figure with close ties to his mother and is arguably the most admired male rap figure among African-American feminists. At the same time he's been willing to take chances musically, never embracing hardcore gangsta-rap, but yet able to include snatches of pop, R&B, reggae and funk into his music without being assaulted with cries of sellout. He's even survived the tragic death of longtime friend and original Boyz member Troy Dixon aka T-Roy in 1990.

During the early '90s, Heavy D began to expand his business opportunities, launching not only an acting career, but also beginning to develop his skills as a music industry mogul; by 1996, he had become one of the presidents of Uptown Records. He didn't abandon his recording career, even though his albums weren't quite as popular as they were in the late '80s. Both 1992's Blues Funk and 1994's Nuttin' But Love were moderate hits, with both albums reaching gold status. Even though his success was consistent, it wasn't splashy, so it came as a bit of a surprise that his sixth album Waterbed Hev debuted in the Top 10 upon its spring 1997 release. Such a placing confirmed that Heavy D was one of the few hip-hop stars from the late '80s that neither burned out or faded away -- he has become one of the few rap artists able to carve out a lasting career.