The Many Heartbreaks Bobby Brown Has Endured in His Life

The Grammy winner's personal blows include the deaths of two of his children in six years, the demise of his marriage to Whitney Houston and their shared struggles with drug abuse.

By Natalie Finn Nov 20, 2020 8:00 AMTags
Watch: Bobby Brown's Son Bobby Jr. Dead at Age 28

Every little step along the way, Bobby Brown has seemingly always had to take the good with the bad.

The 51-year-old artist defied his hardscrabble upbringing in Boston—one of eight kids born to a construction worker father and teacher mom who at one point got involved with the wrong people and stashed a brick of cocaine in their freezer—to blow up big with New Edition as a teenager. He moved on to a successful solo career, selling millions of records and winning two Grammys. Over the years he fathered seven children.

But his eventful life has been pockmarked by tragedy, the latest coming Wednesday with the death of his son Bobby Brown Jr., his third-eldest child and one of his two with ex Kim Ward. The 28-year-old was found dead at his Los Angeles-area home, the cause unknown as yet. Authorities say they don't suspect foul play.

"Please keep my family in your prayers at this time," Bobby said in a statement Thursday night. "Losing my son at this point in our lives has devastated my family. There are no words to explain the pain."

Celebrity Deaths: 2020's Fallen Stars

Bobby's attorney Christopher Brown said that Bobby Jr. "was not feeling well a couple days before his death, with flu-like symptoms. This is a tragic loss and we will let the authorities conduct their investigation of his death."

The loss comes five and a half years after the death of daughter Bobbi Kristina Brown, Bobby's only child with Whitney Houston, who spent six months in a coma after being found unconscious in her bathtub—just a few years after Houston herself drowned in a bathtub.

Even for a man who at an early age got used to struggling as much as he's succeeded, there's been a lot to handle.

Maury Phillips/Getty Images for BET

In fact, Brown has credited a tragedy he experienced at the age of 11 for inspiring him to make something of himself.

In 1981, his best friend Jimmy Flint was fatally stabbed right in front of him after confronting a guy outside a party who was trying to steal his bike (the bike itself one of a pair Jimmy and Bobby had stolen hours beforehand). In his 2017 memoir Every Little Step, Bobby called Jimmy's death, which sent him reeling, the "catalyst" that prompted him to get serious about making music.

"After I emerged from my deep funk," he wrote, "I vowed to myself that I had to get out of OP [housing project Orchard Park] and Boston. It was the only way I could see myself surviving to my eighteenth birthday."

Whitney Houston's Highs & Lows

He started boxing at a local gym and performing in talent contests around town—one of which was fatefully sponsored by talent manager Maurice Starr.

Long story short, Bobby ended up forming New Edition with his childhood friend Michael Bivins, the two of them having already performed together in a local dance crew called the Transitions, and a few other local kids, Ricky Bell, Ronnie DeVoe and Ralph Tresvant. With Starr ushering them along, they released their first album, Candy Girl, in 1983.

Bobby was the youngest member and, as he remembered it, they often handled their issues like the kids they were.

"We had plenty of fights," he recalled with a laugh to Rolling Stone in 1989. "Plenty, plenty of fights." (However, he also insisted at the time, they weren't into drugs as the rumors would imply. "We was into girls," he said. He later quipped in his book, "Once we started, they couldn't keep enough condoms on that damn bus." He also revealed that he got shot in the leg one night, running away from then-new girlfriend Kim's possessive ex-boyfriend.)

Jeff Kravitz/FilmMagic, Inc

After a few years, Bobby quit the group to go solo. (Ricky, Michael and Ronnie went on to form Bell Biv Devoe.)

"When I was in New Edition, I was forced to grow up," the Don't Be Cruel artist told Rolling Stone in 1989. "It was rough for us, being kids. I think I still have the youngness in me, but when it's time for business. it's time for business, I just don't want to be taken advantage of." (The group had tangled with Starr over what they felt was his unfair share of their earnings. At the time of the interview, Bobby had his brother Tommy and mom Carole Brown managing his affairs.)

By then a man of faith, which he continues to be to this day, Brown added, "No matter what happens in life, you gotta deal with the problems. I was always taught this by my mom and dad. No matter what, you can't let them break you down. Once they see that you're broke down and you can't take it no more, boom, right over the edge you go. That's when you lose it all."

He wrote that he made enough money off of "Girlfriend," his first solo hit, to move his parents and siblings from Boston to Los Angeles, feeling blessed and totally unprepared for the trappings of fame and fortune still in his future. 

A slew of arrests, starting in 1990, for battery, DUI, drug possession, failure to pay child support and more were ahead of him, but in the late 1980s Bobby said he wasn't doing any other drugs aside from smoking weed and drinking alcohol. His 1988 song "My Prerogative" served as a musical retort ("Everybody's talking all this stuff about me / Why don't they just let me live") to the rumors. 

He was dating Janet Jackson when he met Whitney Houston at the Soul Train Music Awards in April 1989 and the "I Wanna Dance With Somebody" singer, six years his senior, asked if she could hang onto the jacket he wore onstage. They exchanged numbers, she invited him to her birthday party, and it was on from there.

Ron Galella, Ltd./WireImage

"Even while I was in it, it would feel like those fifteen years of our lives flew by in a blur," Bobby wrote in his book. They got married on July 18, 1992, and welcomed Bobbi Kristina on March 4, 1993.

As the years went by, their turbulent love affair became known more for its lowlights: Whitney's battle with drugs that resulted in the vocal decline of one of the most revered pop stars of the 1980s and 1990s, the way in which they seemed to bring out the explosive worst in each other, their surreal 2005 reality show Being Bobby Brown that perhaps hastened the end of their marriage in 2007.

It was widely assumed that Bobby had brought Whitney down, but in more recent years, it's become clear that her own demons existed long before she met her husband.

Bobby recalled trying cocaine for the first time in the 30 days leading up to their wedding, Whitney having told her 23-year-old groom to get all the rock star antics—drinking, drugs, women, whatever—out of his system before they tied the knot. He didn't know his bride used cocaine on occasion until their wedding day, when he walked in on her before the ceremony snorting a line and she said, "Okay, well now you know—I do coke sometimes."

Bobbi Kristina Brown's Life in Pics

It would be a hobby they'd eventually share. Then it was onto crack and snorting heroin.

Meanwhile, being one half of the most famous couples in the world, let alone the music business, didn't prevent Bobby's past life from getting the drop on him, either.

On a trip back to Boston in 1995, another friend, Steven Sealy, who was also engaged to his sister Carol at the time, was fatally shot while he was sitting in Bobby's Bentley—bullets that he believed were meant for him, Bobby shared in his book. It took almost 20 years for Carol to start talking to him again.

In one of several sections of Every Little Step in which other people close to Bobby weigh in, Landon Brown, Bobby's eldest child (mom is Melika Williams), recalled going to live with his dad and Whitney in 1998. After a few months, Bobby had to briefly go to jail for a DUI.

"How are you doing, Dad?" Landon remembered asking on the phone. To which Bobby replied, "How the f--k you think I'm doing, I'm in jail!"

F. Scott Schafer/Bravo/NBCU Photo Bank

Bobby lamented, "Our daughter was growing up in the middle of all this. She often saw her mother and father high, and was around the two of us when we were f--ked up." They tried to hide it, "But how much quality time can you spend with your daughter when you're high all the time?"

Bobby and Whitney weren't yet divorced when he started dating Alicia Etheredge, but they were acrimoniously separated.

"I think if anyone ever knew us, if anybody ever spent time around us... they would know how we felt about each other," he reminisced of Whitney on Today in 2012. "They would know how happy we were together." But Being Bobby Brown was indeed a "wakeup" for them. "We [were] able to see that our drug use had affected our relationship, had affected the love that we felt for each other," he said.

His daughter LaPrincia Brown, his other child with Kim Ward, recalled that, after Bobby moved out, this was around the time Nick Gordon started spending a bunch of time with Bobbi Kristina, and the two of them would smoke pot with Whitney. The teen was already drinking alcohol on nights out with her older half-sister, LaPrincia remembered remorsefully—but she suspected Bobbi Kristina was already consuming alcohol at home too.

Reality TV Curse: 23 Divorces That Came After Cameras Invaded

Bobby and Whitney finalized their divorce in 2007. He and Alicia welcomed son Cassius in 2009 and got engaged the following year.

Kevin Mazur/AMA2009/WireImage

But then a slew of loss followed. Bobby's mother, Carole, died unexpectedly of a heart attack in 2010. She was 69 and had resettled back in L.A. to be closer to her new grandchild and to help care for her estranged husband, Bobby's father, Herbert Brown, who'd been battling cancer. He lost that fight on Dec. 11, 2011, at the age of 82.

Then, on Feb. 11, 2012, Whitney was found drowned in the bathtub in her suite at the Beverly Hilton, her death later attributed to heart disease exacerbated by cocaine use.

"I felt like I was trapped in a particularly vicious place in hell," Bobby wrote. Bobbi Kristina, 18 at the time, was briefly hospitalized in her grief after mixing Xanax and wine and becoming lethargic.

To put it mildly, Bobby wasn't on good terms with his ex-wife's family, and he didn't approve of most anything they did after Whitney died, from her huge, televised funeral, to their participation in the reality show The Houstons: On Our Own later that year.

Kevin Mazur/BET/Getty Images for BET

In the meantime, Bobby married Alicia in Hawaii on June 18, 2012—two months after being arrested for DUI. He checked into rehab that August as part of his plea deal to avoid jail time. But then he was arrested again in October after failing a field sobriety test, and in February 2013 he was sentenced to 55 days in jail.

That at least marked the end of his run-ins with the law, if not other troubles.

On Jan. 31, 2015, Bobbi Kristina was discovered unconscious, submerged in water in her bathtub, eerily reminiscent of what happened to her mother. She remained in a coma until she died on July 26, after which she was buried in New Jersey next to Whitney. She was 22.

Her father was too distraught to do much, so he willingly let his late ex-wife's family take over all the funeral preparations. In his book he called the service "lovely, a fitting memorial for my baby."


Bobbi Kristina had been living with Nick Gordon at the time of her accident (there was initial confusion over whether they were married or not—they were not), and the following year he was found liable in her death. But there was no way the troubled young man, who opened up about his own drug use on Dr. Phil, was going to be able to pay the $36 million in damages awarded to Bobbi Kristina's family.

"It's not a mystery to me," Bobby told ABC News in 2016, referring to his daughter's fate. "The same thing that happened to my daughter is what happened to Whitney...There's only one person that was around both occasions. Only one person who says they were there to protect them…and he didn't."

In a sad, if not shocking, coda to the whole saga, Nick died in a Florida hotel room on Jan. 1 after an accidental heroin overdose. He was 30.

Jason LaVeris/FilmMagic

In Every Little Step, Bobby credited Alicia for helping him put his life back together after his marriage to Whitney, the love of his life, crumbled.

"Then I had to find a way to get through the loss of my child," he wrote. "But I take one day at a time, keep putting one foot in front of the other—and continue to be a strong, loving presence for Landon, LaPrincia, Bobby Jr., Cassius and Bodhi [his daughter born in 2015]. Not to mention Alicia. That defines me, more than anything else you might have ever heard or read about me."

He and Alicia welcomed another daughter, Hendrix, in 2016.


The artist, who was due to hit the road again this year on the RBRM Tour before the pandemic put a stop to most concerts, continues to take it one day at a time, processing the good along with the sad. On the fifth anniversary of Bobbi Kristina's death, he wrote, "There's no way to explain how I feel. I miss you so much little girl you stay in my heart on my mind every day daddy loves you."

But now he has lost Bobby Jr., who was a musician like his dad. Landon wrote in tribute to his half-brother on Instagram, "I love you forever King."

Bobby's last Instagram post before his son's death was on Nov. 17, a photo of a Thanksgiving dinner that included the question, "What are you thankful for?"

Asked in 1989 if he might have been happier when he was poor, an unknown guy living in Boston, Bobby—already feeling the need to rediscover himself amid the pitfalls of fame at 20— told Rolling Stone, "Yes, very much so."

Thinking it over, he added, "I am poor. I'm poor in happiness."

Latest News