Bobby Brown, even well into his 40s, is still known as the bad boy of R&B. In the past few decades, Bobby’s racked up a long rap sheet of arrests, drug-use, arrogant behavior, lewd stage shows, and always rocky (later televised) marriage to and break-up with the late Whitney Houston.
But back in the mid-'80s, Brown was a just a frustrated teenager from Roxbury, Massachussets trying to be the star he always believed he was destined to become. After leaving the hit group New Edition in 1986, his first solo album (boastfully titled King of Stage) faltered. It seemed, at age 17, Brown would just be another music game statistic of a cocky bandmember who’d made the bad decision to go solo.
Everything was riding on Bobby Brown’s follow-up album, Don’t Be Cruel.
Released in 1988, the album’s title track was a hit, but the second single is what sealed the deal. Produced by Teddy Riley, “My Prerogative” was more than just a song with a $10 word as its title. For Bobby Brown, it was a sinister yet triumphant roar of a young lion loudly proclaiming himself king of his (New Edition) pride. “My Prerogative” combined a futuristically funky bassline with prescient lyrics: “They say I’m crazy, I really don’t care/That’s my prerogative/ … Some ask the question, 'Why am I so real?'/But they don’t understand me/They really don’t know the deal.” And in one stanky swoop, Brown leveled the R&B playing field, eclipsing acts like Johnny Kemp, Keith Sweat, Al B. Sure! and his former hit-making brethren, New Edition.
“My Prerogative” went on to be an anthem, Brown’s biggest hit and the song he is most closely associated with. It defined his career and established his brand, spawning sound-alike songs and influenced countless acts to follow (even Britney Spears covered “My Prerogative,” in one of her many attempts to stay relevant). He released two more hit songs off Don’t Be Cruel album, “Every Little Step” (#1 on Billboard’s Hot 100 & Hot R&B/Hip Hop songs) and “Roni” (#2 on both the Hot 100 & Hot R&B/Hip Hop charts) and had other hits, but nothing would ever equal or surpass the impact of “My Prerogative.”