When his second album, Don't Be Cruel, hit #1 US in 1989, Brown was just a few weeks shy of his 20th birthday. This made him just the fourth teenager to have a #1 album in America, following Ricky Nelson, Stevie Wonder and Tiffany. Debbie Gibson became the fifth when her album Electric Youth hit #1, replacing Don't Be Cruel at the top spot.
He was 12 years old when he formed New Edition with his childhood friends Ricky Bell, Michael Bivins,
Ronnie DeVoe and Ralph Tresvant. He was the first to leave the group, getting out in 1985 because he felt he was being exploited. Brown says the group members were getting $500 a week while their record company was making millions.
Growing up in the Roxbury area of Boston, he had it rough. He was one of eight children in a poor family. Unsupervised most of the time, he ended up hanging out with gang members, and when he was 10 years old he was shot in the knee during a skirmish. A year later, his good friend Jimbo Flint was stabbed to death at a party.
In 1989, he had his own 900-number: 1-900-909-BOBB. Callers would be greeted (for a fee) by a different goofy message from Brown each day. At its peak, it got about 12,000 calls a day.
Soon after his 1988 album Don't Be Cruel was released, he went on tour with Al B. Sure! and New Edition on New Edition's Heart Break tour. When the tour started, he was the opening act and given about 10 minutes to perform. By the end of the tour, his album was taking off and many in audience were there to see him. He ascended to second on the bill and his set was extended to 45 minutes. After this tour, he set out on his own just weeks later, filling the same venues as a headliner.
Brown had a tumultuous marriage with Whitney Houston from 1992-2007, part of which was chronicled on the reality series Being Bobby Brown. The pair had one child, daughter Bobbi Kristina.