Black Rob began associating with the label as early as 1996, appearing on the Bad Boy remix to 112's "Come See Me". He was then featured on several other Bad Boy releases including remixes to Faith Evans's "Love Like This" (1997) and Total's "What About Us" (1998), the single "24 Hours to Live" (1997) from Mase and albums by Puff Daddy & the Bad Boy Family (1997) and The Notorious B.I.G. (1999). He also made two appearances on Cru 1997 album Da Dirty 30, as well as albums by Ol Dirty Bastard, Channel Live, The Madd Rapper, Benzino, Tony Touch, and others.

These guest appearances earned him a media buzz and he kept attention with the hit single "Whoa!". Following this, the album Life Story was released in 2000 and rose above Platinum sales. Despite subsequently appearing on releases by P. Diddy and G-Dep, he was unable to follow up with another hit single and seemingly fell into obscurity. His second album, The Black Rob Report failed to perform as strongly as his debut and quickly disappeared from the Billboard 100 charts.

Now he is preparing for a comeback with the support of Duck Down Music Inc. to release his next album "Game Tested, Street Proved" this Spring.