Born in a Boston housing project in 1969, Brown displayed his onstage prowess at an early age: during the intermission of a James Brown show at Boston’s Sugar Shack, his mom put four-year-old Bobby—the youngest of five children—on stage to dance. At 7 or 8, he became serious about singing and dancing, performing at school talent shows and forming his own band, Bobby and the Angels. A mischievous child—he routinely stole new pairs of sneakers—Brown was an average student and ran around with the proverbial wrong crowd, experiencing street violence at a young age when seeing his best friend stabbed to death. At 11, he entered a talent show with friends Michael Bivens, Ricky Bell and Ralph Tresvant and captured the attention of producer Maurice Starr. The group of friends—later known as New Edition—released a string of bubble gum pop hits—“Candy Girl,” “Mr. Telephone Man,” and “Count Me Out”—before Brown left in 1986 to strike out on his own.

His first album, King of the Stage, peaked at No. 88 on the Billboard 200—not exactly an auspicious debut—but it did produce the hit “Girlfriend.” Brown’s next effort—the chart-busting Don’t Be Cruel—propelled the 20 year-old into superstardom overnight. With hits like the title track and “My Prerogative,” Brown’s use of gospel sounds with hip-hop lyrics spawned a new style called New Jack Swing. Soon Bobby Brown imitators began popping up and the star rode the wave of his new-found celebrity. Meanwhile, he experienced his first public brush with the law in 1989: he was arrested in Columbus, Georgia for simulating a sex act on stage. He was fined $600 and continued his performance. In 1990, Brown’s record label, MCA, cashed in on his popularity and released a remix album, Dance!…Ya Know It!, which reached a respectable No. 9 on the charts. He then contributed the theme song to “Ghostbusters II” (1990), On Our Own, which sold over two million copies.

In the summer of 1992, Brown released his third solo effort, Bobby. Though not as big a hit as Don’t Be Cruel, the album did double-platinum business. That same summer, the singer wed the most unlikely woman possible—the squeaky clean pop diva, Whitney Houston, whose talent as a singer and reputation as the Good Girl stood in stark contrast with Brown’s limited vocal range and Bad Boy image. But the two professed true love, so who could argue? Turned out the media had plenty to say about the unusual coupling, as Brown and Houston routinely defended their nuptials in public. The two met at the 1989 Soul Train Music Awards and began dating after Houston invited Brown to her birthday party. But almost as soon as they were married, Brown’s career took a noticeable slide. He was arrested in 1993 for another charge of lewdness on stage—again in Georgia—when he feigned a sexual act on a female dancer. Though Houston’s career skyrocketed on the success of “The Bodyguard” (1992)—both the movie and the soundtrack—Brown suddenly found himself in the backseat, largely ignored and even vilified by the media.

His legal troubles began in earnest in February 1994 when he was arrested at an Atlanta jazz club for failure to appear in court for traffic violations. After a bench warrant was issued, police were tipped off to his presence and converged on the club. Then in April, he found himself in trouble with the IRS for failure to pay back taxes—a bill reportedly totaling $3 million. On the career front, another remix album, Remixes N the Key of B, was released, but resulted in weak sales. Meanwhile, the lawyer fees continued to mount in April 1995 when Brown was arrested for assault at a Disney World night club. He and two members of his entourage beat a club patron to a pulp, resulting in several sutures to repair the man’s face and reattach his ear. After being placed into the back of the squad car, an agitated Brown banged his head against the window and urinated on the seats. Charges were later dropped after settling with the victim out of court.

Things went from bad to worse when security at a West Hollywood hotel room was summoned to Brown’s room after a noise complaint. For some reason, he kicked the guard in the back and was arrested soon after. Meanwhile, Houston began expressing her displeasure with her husband’s behavior in public. The last straw came in September after a drunken Brown blew up after not being invited to a meeting for “Waiting To Exhale” (1995), a romantic drama starring Houston, Angela Bassett and Loretta Devine. With tail between legs, Brown took Houston’s cream-colored Rolls Royce and returned to familiar environs—Boston. While parked outside a nightclub in his old neighborhood, Brown witnessed his sister’s fiancée, Steven Sealy, get shot multiple times by two gunman. Though unscathed, Brown was shaken-up by the incident. Later that year, Brown and Houston reconciled their differences and returned to being a married couple.

In 1996, Brown was cast by actor Martin Lawrence in “The Thin Line Between Love and Hate,” playing the friend of a womanizer (Lawrence) who learns the lesson of feigning expressions of love to the wrong woman. He then reunited with his former New Edition mates for an album and subsequent tour. Though the new release, Home Again, sold millions and topped the Billboard charts, the tour was plagued with false starts and clashing egos. The rejuvenation to his career was temporary, however, as Brown’s personal troubles continued unabated. In December 1996, he was arrested for drunk driving in Miami after a single-car accident that resulted in a crashed Porsche, four broken ribs and a mauled street sign. Earlier that year, he checked into the Betty Ford Clinic for problems with alcohol. While in rehab, he got into trouble with the tabloid press after allegedly calling his wife a lesbian. Brown called the report a “fabrication.”

Despite a limited contribution to New Edition’s reunion album and later walking off the tour after feeling “disrespected” by the rest of the band, Brown tried to re-ignite his solo career, releasing his fourth original album, Forever, in the fall of 1997. Instead, Brown produced a weak and uninteresting album that stalled at No. 66 on the Billboard charts. Accusations of spousal abuse hit Brown in 1997 when he reportedly struck Houston in a hotel lobby. Adding fuel to the fire, the couple was later seen leaving a yacht in Capri with Houston’s face sporting a fresh gash. Both vehemently denied rumors of abuse. Then in June 1998, a woman accused Brown of sexual assault, but the Beverly Hills district attorney dropped the charges for lack of evidence.

In 1998, he was convicted in Fort Lauderdale, Florida for his 1996 drunk driving incident. A weeping Brown was sentenced to five days in jail, a year probation, suspended license, a $500 fine, 30 days in a rehabilitation center and 100 hours of community service. A year and a half later, Brown was arrested for violating the terms of his probation and faced 90 days in prison. Then as the new millennium brought in a new century and new promise for the world, it was the same-old, same-old for Brown. By May 2000, he was in front of a Fort Lauderdale judge for once again for violating probation—his third time. Dressed in prison blue, Brown was deemed a flight risk and was jailed pending his court date.

The pile-on continued when a former girlfriend and mother of his children filed a complaint in New Jersey, claiming Brown owed over $25,000 in back child support while the deadbeat dad was serving time. Meanwhile, rumors of drub abuse rocked Houston, whose fragile frame and fading voice fueled the rumors that the former pop diva was abusing cocaine. The rumors were denied, of course, but the physical evidence was apparent. Brown tried to revamp his career in 2001, appearing in small roles in a pair of movies: the urban comedy “Two Can Play That Game” and the heist drama “The Score” starring Robert De Niro and Edward Norton. Then in 2002, Brown was charged in Atlanta for marijuana possession and trafficking. Though he could have been set free, police held on to the repeat offender after discovering a warrant for dodging a court date relating to his 1996 drunk driving incident.

In early 2003, Brown made an appearance on “The 30th Annual American Music Awards” (ABC), but was spotted by a DeKalb County judge, who issued a warrant for Brown’s arrest for leaving the state of Georgia while awaiting a court date. Later that year, he was sentenced to fourteen days in jail and sixty days of house arrest after being nabbed by police the prior week while dining with his family—again for violating the terms of his probation relating to the drunk driving incident. He rounded out the year by turning himself in after giving his wife a bruised cheek and cut lip. After Houston accompanied him to the police station, Brown was released on his own recognizance.

After serving a sixty day sentence in DeKalb County for violating probation, Brown vowed to never return to jail. Two days later, he was sentenced to ninety days for back child support totaling $63,000. A teary-eyed Brown professed he hadn’t the funds to pay his former girlfriend, Kim Ward, but accounts were somehow settled the next day and he was released. With their personal lives already a media circus, Brown and Houston allowed themselves to be filmed for a reality television series. “Being Bobby Brown” (Bravo, 2005- ) first aired in June 2005 and showed the infamous singer demonstrating how Preparation-H could be used to prevent wrinkles, celebrating a romantic evening with his wife after being released on bail, picking the lock on a hotel mini-bar and dancing a jig at a Chinese restaurant. The sad legal saga continued just a month before the first episode aired when a judge issued a warrant for Brown’s arrest after his failure to appear for a child support hearing.