From a very young age, Bobby Brown knew that he was destined to be in the spotlight. The road he walked to achieve his fame and fortune certainly hasn’t been easy, but the 55-year-old is among the prestigious club of Grammy Award winners and his marriage to the late Whitney Houston has been retold countless times throughout film and television.

The 90s in particular were a pivotal decade for Brown, who met his future wife shortly before they began, not long after launching his solo career after his exit from New Edition. Plenty of change was in the air for the Massachusetts native at this time, including fatherhood, jail time, drive-by shootings, film/TV roles and struggles with substance abuse. Let’s deep dive into some of Bobby Brown’s biggest career moments.

1990

By the time the 90s came about, Brown had already established himself as an R&B pioneer, even without his New Edition bandmates by his side. It was at this time that he took home his first Grammy Award – Best Male R&B Vocal Performance for “Every Little Step,” which came from his second studio album, Don’t Be Cruel. That same project earned the Boston-born entertainer two American Music Awards, a Soul Train Award and a People’s Choice Award. Public ceremonies such as these kept Brown in the public eye for most of the year, including his old group’s reunion at the MTV Awards as well as his performance of “Tap into My Heart.” The song was expected to appear on an LP titled Mystical Magic, but that was ultimately shelved for reasons unknown.

Other opportunities that came the singer’s way in 1990 include a feature on Glenn Medeiros’ “She Ain’t Worth It,” which brought his second number one hit on the pop charts, a collaboration with Babyface on “Tender Lover (Remix),” and a stint on HBO’s family show, Mother Goose Rock ‘n’ Rhyme, where he voiced all three of the famous Blind Mice. On the less flattering side of things, Brown was charged with disorderly conduct for refusing to leave a restaurant following his brother’s arrest – the first of several run-ins with the law throughout this decade.

1991

As his solo career continued to take off, Brown was navigating some chaos and excitement in his personal life. Kim Ward, whom he was in an on-and-off relationship with for over a decade, gave birth to their son, Bobby Brown Jr. in 1991. Unfortunately, her pregnancy was full of emotional turmoil after finding out about her co-parent proposing to Whitney Houston while finishing her first trimester. The recording artists became fast friends after crossing paths at the 1989 Soul Train Awards. After a few years of getting to know her, Brown felt ready to build a steady life with his new lover by his side. Of course, things were nothing short of rocky for them as they began a union out of infidelity.

While things in love were tense at times, Brown was at least able to patch up relationships with New Edition members. He appeared on Ralph Tresvant’s “Stone Cold Gentleman,” which went on to be a top-five R&B hit, and many of the group’s stars came together for “Word to the Mutha!” around the same time. When heading out on his Don’t Be Cruel tour with Al B. Sure! enlisted as his opening act, Brown was once again at odds with the law after simulating sexual acts onstage while performing.

1992

As the New Jack Swing era came to a close, Brown’s Bobby LP managed to deliver some iconic hits to close out this chapter in music history. “Humpin’ Around” is his best-known track from ’92, but “Get Away” and “Good Enough” remain in rotation for many. The 14-song effort was certified Platinum by the RIAA and sold over three million copies; though impressive, the numbers weren’t enough to live up to his past releases. While he handles most of the titles on his own, Brown did connect with Debra Winans for “I’m Your Friend,” Aqil Davidson on “That’s The Way Love Is,” and his wife, Houston, for “Something In Common.”

The former boyband member spent this year and the next touring, but he also found time to tie the knot while dodging tabloid photographers and reporters looking for dirt on his relationship. Houston and Brown’s ups and downs kept them in the media consistently, largely thanks to rumors of infidelity, substance abuse, and domestic disputes, all of which only became worse with time.

1993

The success of “Humpin’ Around” and other Bobby hits followed Brown into 1993, when his and Houston’s first and only child, Bobbi Kristina, was born. The infant later appeared in her parent’s music video for “Something In Common,” and her dad continued his casual string of television appearances with an episode of Out All Night. From an outsider’s perspective, it might’ve looked like things in the Brown household were wholesome, but the new parents both admitted years down the road that their drug use only became more severe as they spent more time together.

“It was a shocker to me seeing her sniff for the first time. It was then I realized we had more in common than I thought. I was new to it and I guess she had been doing it for a while,” the East Coaster shared in a 2022 A&E documentary, as per DailyMail. “That became a problem for us in our marriage. After I got married that is when I started using hard drugs. We were going through the stresses of stardom, fame, money, drugs and rock’n’roll. We started not working, getting high and it became a part of our daily routine.” Things got so bad that Houston once had to pay a $400K ransom for her husband, who had been kidnapped by drug dealers, the National Enquirer notes; the alleged incident was never reported to police, but lives on in pop culture infamy.

1994

At the time of Bobbi’s birth, Brown was already a father of three. His first son, Landon, was born in June 1986 to Melika Williams. The aforementioned Ward is the musician’s second baby mother – she gave him La’Princia in 1989 before her co-parent’s namesake came in 1991. Then came his and Houston’s only baby, though the married pair was hoping to have more children together. Sadly, the “I Wanna Dance With Somebody” hitmaker suffered a miscarriage in 1992, before her successful pregnancy, followed by two more in 1994 and 1996. It was surely an emotional time for both her and Brown, especially coupled with their drug use and pressure from being in the public eye. In terms of his music, the K-Klass remix of “Two Can Play That Game” became Brown’s biggest single in the UK at the time, peaking at number three on their chart.

1995

As he approached the end of his contract with MCA, Brown and the late Tupac Shakur were in talks to have the former sign his next deal with Makaveli Records, or the proposed Death Row East imprint. The “All Eyez On Me” artist was shot and killed in Las Vegas before these plans could come to fruition, leaving the father of seven with no concrete plans for the future. It wasn’t until September 1996 that ‘Pac lost his life, but in 1995, Brown found himself in the wrong place at the wrong time when Steven Sealy, his sister’s then-boyfriend, was murdered in a targeted drive-by shooting. Brown left the scene of the crime with his life, but he was beyond shaken up after witnessing the tragedy.

The rest of the year was full of more turmoil for the struggling creative, including an incident at an Orlando nightclub where Brown and two friends were accused of beating a patron before urinating on a cop car and committing acts of vandalism. Elsewhere, he was cited for battery after authorities accused the genre-bending star of kicking a security guard investigating noise complaints coming from Brown’s room.

1996

1996 was a far more quiet year for Brown, with one of his most noteworthy releases being Martin Lawrence’s A Thin Line Between Love and Hate film. He was also on set for an episode of Family Matters, and lent his vocal talents to the New Edition reunion album, Home Again, leading the charge on songs like “Hit Me Off” and “You Don’t Have to Worry.” As we previously noted, this was when Houston was dealing with her third miscarriage, heightening emotions in the Brown household beyond their normal levels.

1997

After several years without a solo project to share with fans, 1997 saw Brown return on Forever. Its only single, “Feeling Inside,” wasn’t particularly successful, though it did mark his last release under MCA and take him on the road until 1998. In the time before his solo tour, the former reality star was performing across the nation with New Edition, which didn’t go as smoothly as planned. In his A&E documentary, Brown blames his drug use for his late 90s flops.

“I used to smoke preempt – crack cocaine inside weed. You roll them up. I was so high,” the embattled artist admitted of how addiction and paranoia began taking over his life. “I thought Whitney was trying to kill me, I ended up running through a field, I had a 57 magnum on me, cocaine, crack, and weed in this. My addiction affected my career big time.”

Late 90s

The final few years of the decade weren’t easy for Bobby Brown. From being convicted of two misdemeanors from a 1996 car crash that resulted in spending five days in jail to having a warrant issued after his probation officer reported that his urine tested positive for cocaine, the industry icon found himself in trouble with the law time after time.

Thankfully, some of these periods helped Brown to get his head on straight again, allowing him to move towards sobriety after a rollercoaster of a decade. His legacy continues to live on.