He sold three million records and still gets the Rodney Dangerfield treatment. Is he a Nelly clone? Ludacris’ DTP sidekick? A Pop-Tart rapper for bubblegum babes? Nah, son. He’s Chingy. A young MC with a bright-ass future.

Words Vanessa Satten
Images Michael Lavine

I have this problem of thinking that nobody’s gonna try to do me wrong.” On a warm day this past spring, Howard “Chingy” Bailey, Jr. sprawled chest-down across the thick red cushions of an L-shaped couch and cracked a shy smile. The 24-year-old rapper seemed comfortable, well at home in his new four-bedroom mini-mansion in the suburban St. Louis enclave of O’Fallon. Relaxing in a white T, sweats and socks—no shoes allowed on the white carpet—Chingy had banished his family and friends from the living room because they “distract” him. He laughed softly before continuing: “I really got that problem. That nobody’s ever gonna try to do me wrong because I ain’t never do nothing to them. I know that’s a problem. That’s just the type of dude I am. I don’t do nothing wrong to people, so I be expecting nobody to do me wrong.”

No two ways about it, Chingy is a nice guy. And if recent history is any indication, he just might prove that nice guys can finish first. In 2003, Disturbing Tha Peace Records—in conjunction with Capitol Records and Trak Starz Productions—introduced his mischievous Midwest twang to the world via the addictive synth pulse of “Right Thurr.” The song turned into a summer smash, proving that St. Louis rap had more to offer than Nelly, and making DTP’s principals—Atlanta’s golden boy Ludacris and his partner Chaka Zulu—look like geniuses. Chingy’s first full-length offering, Jackpot, debuted at number two on the Billboard Top 200 album chart in July; seven months later, it had spawned three top-10 singles and earned three platinum plaques.

Now, in the industry’s ultra-competitive fourth quarter, the almond-eyed heartthrob is gearing up to release his second effort, Powerballin’. Although it’s been just over a year since the last album, things are different this time around. Not only has Chingy become an instantly recognizable, totally bankable, multi-platinum-selling rap star, he’s dealing with some of the trials and tribulations that have come to seem like mandatory requirements for the position. Citing iffy money and management practices, Chingy has ended (or is in the process of ending) his affiliation with DTP. He’s starting his own company, Slot-O-Lot Records. Meanwhile, in what seems like an inevitability in the post-50-Cent era of beef-for-profit, Nelly set thestage for a St. Louis pop-rap battle with a less-than-friendly reference to his crosstown rival (his archrival, perhaps) on his recently released album, Sweat.

Born March 9, 1980, Chingy grew up on St. Louis’ North Side, in an area called Walnut Park. “The place where there are drugs, guns, gangs,” Chingy explains of his origins, “suffering little kids who don’t have families, bums.” He lived in his maternal grandmother’s house, sharing the two-bedroom space with up to a dozen relatives, including four of his five siblings. “I don’t come from any sort of money,” he says. “My mama was working, and my father was hustlin’, doing him, so we had something, but nothing too much.” When he was 10, Chingy’s parents split and he began shuttling between various residences.

Having written rhymes since he was eight, Chingy got with a neighborhood friend, Justin, and started a rap group. Calling themselves L.S.D., for “Lethal Substance Of Dope,” the two preteens practiced a routine and signed up for local talent shows. “There wasn’t much of a hip-hop thing here at that point,” Chingy says of the early ’90s ’Lou. “There were people trying, but you could count how many on your fingers. But we were trying to make it happen. We were young, trying to hook up performances. And people liked what we were doing, so they would give us a little bit of a chance.”

Throughout his adolescence, Chingy had some minor scrapes with the law. (When he was 12, he was sent to a juvenile detention center for stealing a car. “I knew that was somewhere I did n’t want to be,” he says of the month-long stint. “So I was like, When I get out of here, I’m gonna make sure I don’t come back. Ever.”) But for the most part, he kept his nose clean, attending McCluer North High School, working at a Burger King and focusing on his music.

When Chingy was 16, rapping under the name Thugsy (a.k.a. “H Thugs”), he and Justin brought in a third partner, and L.S.D. became Without Warning. In 1996 the trio signed to a local start-up called 49 Productions, put together a CD of their songs, and hit the road. With limited financial backing, they found themselves performing in such disparate places as Georgia, Colorado, California and Alaska. “We wasn’t really making any money,” Chingy says. “And we spent more than we made anyway, so we weren’t really getting anywhere. So we just moved on back to square one. Just trying to meet people and get in the studio.” The group soon dissipated.

By the time he graduated high school in 1999, Chingy had fathered a son, Mykel. He did some small-time hustling and worked odd jobs to pay the bills, but he was always looking to stay involved with rap. He started another trio, called 3 Strikes, with two other guys he knew from growing up. One of them, Ahmad had an older brother, Ali, who rapped in a fivesome from the University City section of town, the St. Lunatics, which had been making noise locally for a few years.