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 1999 and rose above Platinum sales. Despite subsequently appearing on releases by P. Diddy and G. Dep, he did not make another hit single: his second album, The Black Rob Report failed to perform as strongly as his debut and quickly disappeared from the Billboard 100 charts. In his earlier years Black Rob headed the street rap team which he named "Alumni". In 2005 Jemal Mosley from Off The Block Entertainment started managing Black Rob's career. In 2010 he parted from Bad Boy, and signed to independent label Duck Down Records. As of 2010 he was working on a new album titled Game Tested, Streets Approved due to be released the following year.
Black Rob also started his own independent label, Box and One with Jemal Mosley.
Ross has a history of arrests starting in childhood and continuing after his record label signing and album release. He was sentenced to seven years in prison in 2006 after failing to appear in court for his sentencing (which was to be 2 – 6 years initially) on a charge of grand larceny from 2004, in which he pleaded guilty to criminal possession of more than US$6,000 worth of jewelry stolen in a hotel. He was released from prison in May 2010, and was interviewed by BET two hours later.