It’s hard to believe it’s been 25 years since the release of Bobby Brown’s groundbreaking Don’t Be Cruel. New-jacking the title from an old Elvis Presley song (of which most of his fans couldn’t care less about), in 1988 Brown’s brilliant sophomore album changed that decade’s R&B game, making the music more youthful and aggressive.

Dropping from Black pop heaven in June of that year, the entire album would go on to become the one of the main soundtracks of the summer. From the bouncy title track produced by L.A. Reid and Babyface—which also severed as the first single—to the hard-hitting “My Prerogative” constructed by Teddy Riley and Bernard Belle, the disc took Bobby Brown out of his R&B pigeonhole and elevated him to an international superstar.

As a budding music writer, I was impressed with Bobby’s macho swagger and slanted flattop Gumby haircut. He was on stage grabbing his nuts and looking menacing; off-stage he was hanging-out and partying. I respected Michael Jackson, but he only sang about being bad; Bobby Brown was a bad boy for real. As rock critic Chuck Eddy once wrote in Spin, “Bobby slayed anybody who got in his way.”

Steve Manning, Bobby’s first publicist, recalls: “Bobby knew he had talent and he wanted everybody else to know it too.” But having been kicked out of New Edition in 1986, and releasing a lukewarm solo album, King of Stage, the same year, not many consumers or record executives had much anticipation for Brown’s 1988 follow-up.

King of Stage wasn’t the blockbuster that chocolate cities across America expected. Instead of highlighting Brown’s rebellious side, songs like “Girlfriend” and “Girl Next Door” weren’t all that much different from New Edition’s material. While “Girlfriend,” written and produced by Cameo leader Larry Blackmon, soared to number one on the R&B charts, King of Stage failed to generate much buzz. “The album sold about 500,000 copies, but Bobby fans didn’t feel the record represented him,” says former MCA Records publicist Juanita Stephens. “They kind of dismissed it.”

A newly hired young executive named Louil Silas Jr. was determined to mold Brown into the soul sensation he believed him to be. With no one at the company really paying attention to Bobby’s career, Louil put relative newcomers L.A. Reid, Babyface and Teddy Riley in the studio with the underdog singer.

Babyface and Antonio “L.A.” Reid were the musical beacons behind their own group, The Deele, as well having produced the Whispers’ classic, “Rock Steady.” The duo had also worked with Silas on tracks for upcoming MCA acts Pebbles and The Boys. “Louil was one of the few people who wasn’t afraid of [SOLAR Records boss] Dick Griffey, which was the reason we got our shot to do Bobby,” Babyface says.

Visiting the production duo in their Hollywood apartment, Bobby listened to the Babyface-sung demos of “Don’t Be Cruel” and “Every Little Step.” Says Babyface, “We wrote songs that were sweet and nice, but they also had a little edge to them. Bobby was pretty agreeable when he heard the material.”

Not long after that initial meeting, Brown began recording with L.A. and ’Face at Silver Lake Studios in Los Angeles. “Bobby had a pure vibe and a passion that was unmistakable, but he just needed a little guidance,” says Babyface, who cites Don’t Be Cruel’s third single, “Roni,” as his personal favorite. “We just went in and recorded without problems. We didn’t spend a lot of time in the studio. But listening to Bobby Brown record those songs, it was obvious that he had star power.”

Meanwhile, on the opposite side of the country, a Harlem-raised youngster named Teddy Riley was preparing his own brand of funk to present to Brown and Silas. “I came from the streets, so I made street music,” Teddy Riley says of the New Jack Swing sound that he invented in his living room in the St. Nicholas Houses.

“I also added in a little gospel,” he says, “as well as the groups I had seen at the Apollo when I was a kid”—groups like Parliament and Al Green. Having experimented with this new sound on Johnny Kemp’s “Just Got Paid,” Keith Sweat’s “I Want Her,” Al B. Sure!’s “Nite and Day” and his own group Guy, Teddy was ready for the New Jack Swing sound to gain worldwide popularity.

Screenwriter Barry Michael Cooper—who coined the term “new jack swing” in a 1988 Village Voice article and also wrote the screenplay for New Jack City—says, “On Don’t Be Cruel, both Teddy and L.A./Babyface propelled soul into the digital age: New Jack Swing. Teddy invented it, and L.A./’Face refined it. The music was an amalgam of soul, hip-hop, jazz, gospel and fusion. It was an operatic soundtrack to the street cinema of their collective existence. And it worked.”

Having worked alongside Teddy on the amazing tracks “My Prerogative” and “I’ll Be Good to You,” musical arranger Bernard Belle told writer Andrew Knyte, “Bobby Brown was a ball of energy, and he was never tired. In the studio, if you told him to do something and it didn’t come out right, he’d be willing to do it over and over and over again. He was going to do whatever it took to get the project done when he was in the studio while we were recording for the Don’t Be Cruel album. That’s the best way to describe Bobby back then—he was hungry.”

While Bobby was jetting between coasts, putting in the hours to complete his project, MCA staff barely realized the boy was working at all. “There was no buzz in the office about the Bobby Brown record,” states publicist Juanita Stephens. “In fact, Don’t Be Cruel and New Edition’s new album [N.E. Heartbreak] was set to ship the same day. Anticipation was high for New Edition, but I had to be fair to both.”

When Don’t Be Cruel was released on June 20, the record was so strong it gave 19-year-old Bobby a whole new identity. He wasn’t a kid anymore. The power and greatness of that music defined a new movement in Black pop. Although a few months later he became the opening act on the N.E. Heartbreak Tour (also featuring Al. B. Sure!, Troop and Levert), as Don’t Be Cruel neared the triple-platinum mark, Bobby started headlining his own worldwide tour.

Some nights, he’d be on stage non-stop for nearly three hours. Strolling out in a bowler hat and dripping with gold chains, Brown’s show was all about music and seduction. “To see Bobby Brown on stage was like watching James Brown, Jackie Wilson and [Russian ballet dancer Vaslav] Nijinsky all at once,” says Barry Michael Cooper. “His shows left me speechless.”

Putting the same energy into his videos for “My Prerogative” and “Every Little Step” (the song that won him a Grammy in 1990) just made him that much more popular. Driving the mostly female crowd into frenzies with his intense choreography and poetry of the pelvis, Bobby was in his glory.

Still, even if he was trying to soulfully mack the girls, the guys in the audience also loved Bobby because he came off like your badass little brother or bugged-out homeboy. Unfortunately, he seemingly didn’t have the same kind of creative discipline to maintain his success.

Beginning in the early 1990s, Bobby went from being an untouchable superstar to becoming a public spectacle as drug accusations between he and Whitney Houston became popular tabloid fodder. In addition, there were numerous arrests, crazed incidents, drunken outbursts and an attempt to murder him in his hometown of Boston. His brother-in-law Steven Sealy was killed, gunned down in Whitney Houston’s Bentley while Bobby sat in the passenger seat.

After courting and marrying the late pop diva in 1992, things only got worse. “Bobby’s private life was also his public life,” explains Cooper. “Bobby was not able to sustain his career because it almost seemed that not only did he not duck scandal, he invited it. Scandal was both his badge of honor and his scarlet letter. Somewhere along the way, he could not differentiate between the two.”

While Bobby Brown might’ve become the Sly Stone of the new jack generation, there’s no denying the cultural impact of Don’t Be Cruel. While Justin Timberlake, Chris Brown and Drake often cite Michael Jackson as their main influence, it’s obvious they all owe heavy stylistic debts to Bobby Brown.

Cultural critic Michael A. Gonzales has written cover stories for VibeUptownEssenceXXL, Wax Poetics and elsewhere. He’s also written for New York and The Village Voice. Read him at Blackadelic Pop and follow him on Twitter @gonzomike.