By 1988, Bobby Brown’s career was in freefall. Two years prior, he was dismissed from New Edition, the pop-R&B quintet he started with four Boston friends — Ricky Bell, Michael Bivins, Ronnie DeVoe and Ralph Tresvant — in part because of his rebellious streak. Though the group’s label, MCA Records, quickly signed him to a solo deal, his first solo release, 1987’s King of Stage, failed to match the highs of his New Edition days. Initially, signs of success showed — lead single “Girlfriend” topped the R&B charts for two weeks, and pushed the album to No. 12 on the R&B side — but any buzz faded once second single “Girl Next Door” stalled at No. 31. With no crossover hit in sight, the album maxed out at No. 88 on the Billboard 200.
“It was really a solo New Edition album,” Brown told Fred Bronson, author of The Billboard Book of Number 1 Hits, in the early 1990s. “The voice was there, the voice they remember from ‘Candy Girl.’ It didn’t work out for me. We had to regroup and find out what my identity was as a singer.”
To forge that identity, Brown enlisted a new slate of producers, including Teddy Riley, Gene Griffin and, most notably, the rising team of Antonio “L.A.” Reid and Kenneth “Babyface” Edmonds, who were all architects of a fusion sound termed new jack swing — a blend of dance-pop and hip-hop’s syncopated rhythms with R&B vocal style. As the album — Don’t Be Cruel – took shape, Brown, too, flexed his lyrical and thematic boundaries, forgoing most of the bouncy, bubblegum pop and yearning ballads of the New Edition era in favor of a rawer swagger, in the footsteps of Janet Jackson’s similar transformation with her third album, Control, in 1986.
And like Control, Brown’s Don’t Be Cruel exploded. The run started on July 23, 1988, when the album debuted on the Billboard 200 at No. 74 and the title track and lead single opened on the Billboard Hot 100 at No. 88. From there, both jumped up their respective charts, each cracking the top 10 by October. With the single “Don’t Be Cruel” peaking at No. 8 that month, the album danced around the lower reaches of the Billboard 200’s top 10 until a reinforcement arrived in the form of the even more successful second single, “My Prerogative.” The track, which Brown co-wrote with Gene Griffin, with additional uncredited help from Teddy Riley and Aaron Hall, ascended to No. 1 on the Hot 100 in January 1989, and, thanks to that push, carried the Cruel album to the top of the Billboard 200 the next week, on Jan. 21, 1989, nearly six months after its arrival.
The new Bobby Brown and new jack swing dominated 1989, with Cruel leading the Billboard 200 for six straight weeks and finishing the year as the chart’s No. 1 album. Though “Prerogative” was its only Hot 100 No. 1, the album maintained its strength with additional hits “Roni” (No. 3) and “Every Little Step” (No. 3). Brown’s star power was so strong at the time, in fact, that he paused promotion on Cruel to release a single from the Ghostbusters II soundtrack, “On Our Own,” which raced to No. 2. After that brief interruption, he resumed his Cruel streak with a fifth top 10, “Rock Wit’Cha” (No. 7).
While the early 1990s offered personal and professional wins for Brown — his next album, 1992’s Bobby, yielded two Hot 100 top 10s and he married superstar Whitney Houston and reunited with New Edition for an album and tour in 1996 — his career stalled in the latter part of the decade and into the 2000s as legal and personal troubles mounted. He was repeatedly arrested for drug and alcohol-related offenses, and his troubled marriage to Houston sparked tabloid headlines and a panned reality TV show, Being Bobby Brown, before their 2007 divorce.
Since, the singer has largely remained on the touring circuit with New Edition in 2011, and the group was the subject of a three-part BET miniseries, The New Edition Story in 2017, with Tyler Marcel Williams and Woody McClain portraying the R&B star at various ages. “I’ve been through so many things in my life,” said Brown at a screening in Boston on Jan. 8, 2017, two weeks before the series’ premiere. “But I’m sane, I’m sober, and I’m alive. And there’s so much I’m thankful for.”