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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.

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In 2000, of course, the Lunatics—well, one of the Lunatics, Nelly—put St. Louis on the rap map. Hipping the world to a new pronunciation of the letter “R” (an element of the dialect he called “Country Grammar”), Nelly sold an astounding eight million albums, drawing all hip-hop biz eyes to the home of Eero Saarinen’s famed arch. “I’m cheering them because I’m happy for them,” Chingy says, remembering his reaction to the ’Tics’ sudden success. “They broke through, being from St. Louis. That’s not only good for them, but now it’s giving my city an opportunity. Now you can be at a club and you might bump into an A&R or some music-inclined person.”

Sure enough, 3 Strikes were soon doing regional dates, opening for Nelly and the St. Lunatics. Even with the added exposure and filial bond to fame, though, they couldn’t make it happen for themselves. The trio split over personal differences in 2001. Chingy had grown close with the St. Lunatics’ manager, T-Luv, who agreed to help shop him as a solo act. Talk of a solo deal with the St. Lunatics or Universal Records never materialized, but T-Luv hooked the young rapper up with local producers Shamar “Sham” Daugherty and Alonzo “Zo” Lee, a.k.a. the Trak Starz, who helped him with his first solo cuts. “Chingy was the one that stood out of the group, that had the most charisma,” says Sham, comparing the then-struggling rapper to his former partners in 3 Strikes. “He just had the presence and delivery. We decided to sign Chingy to a production deal.”

The Trak Starz were being managed by EbonySon Entertainment, a firm co-owned by Def Jam South vice president (and Disturbing Tha Peace CEO) Chaka Zulu and his brother Jeff Dixon. When Chaka asked to hear some of the artists the Trak Starz were working with in 2002, they played him five of Chingy’s songs. “Out of the five songs, I thought three of them were singles,” says Chaka Zulu. “One of them was ‘Right Thurr.’ It only had two verses on it. So I was like, Okay. And I listened to it over and over again—I really feel this.”

"Chaka must’ve liked the song,” Chingy remembers. “’Cause after that, we went right to the studio to mix and master that song. We finished most of Jackpot and sent it to Chaka and a couple of other people. I hoped that somebody was gonna call back and be like, ‘We’re diggin’ this, and we would like to work with you...’ Chaka and them happened to be the one to call back and be like, ‘We can do something with this.’”

With Chaka Zulu’s contacts and resources behind the project, record labels started sniffing at Chingy. “I think a lot of them were still skeptical, ’cause they was like, ‘Was Nelly a fluke?’” says Trak Star Zo. “But they was still kind of looking, because Nelly sold so many records.” Chaka invested out-of-pocket to press up a stack of “Right Thurr” 12-inches and sent copies to club DJs and radio stations, earning some regional airplay and increased major-label interest—most notably from Capitol Records.

“Then Chaka was like, ‘What y’all think about Chingy being on DTP?’” says Chingy, of the origins of his multitiered deal. “We was thinking, ‘Hey, who cares, as long as we get out? We want to get cash and do the video and put the music out and let’s be heard...’ There’s the Trak Starz contract, and Trak Starz made a contract with DTP to use my service, use my music, through their deal. That’s how the contract went. I ain’t got no straight contract with DTP. Chaka and Jeff were managing me then, but there was no management contract.”

By mid-2003 “Right Thurr” was a massive hit. At the same time, the new DTP affiliate was trying to find his place on a roster with one already established star, Ludacris, and a crew of mostly Atlanta rappers hungry for just the type of success Chingy was enjoying. Folks like Shawnna, I-20, Lil’ Fate and Tity Boi—artists introduced on DTP’s 2002 posse album Golden Grain—had been waiting to release solo efforts, and now they were getting put on the back burner. “There’s a lot of attention on me,” Chingy says. “People are like, ‘How you put him before everybody?’ I’m coming into this bitch like, ‘I’m just trying to do what I gots to do.’ When I first came around, you could sense it. That people was really like, ‘Uh, yeah. Okay. Whatever.’ They didn’t know me. Once you get to know me, I’m a cool guy, good dude. The doors open up and they see the real you. So I was cool with everybody. Luda’s a cool dude. He was busy, just like I was busy working on my stuff. Luda was busy doing his thing, but eventually, as it grew, I came around Luda more.”

“Right Thurr” was followed by the July release of Jackpot. The album spawned two more huge singles—the infectious “Holidae In” featuring Snoop, and the lovey-dovey “One Call Away”—on its way past 2.8 million in sales. Meanwhile, as Chingy’s face became an everyday sight on MTV and BET, his management paperwork was never worked out. “I’m not stupid,” says Chingy. “I was like, ‘When we gonna do the management contract thing?’ They [EbonySon Entertainment] was like, ‘Don’t worry about that. It’s cool.’ I was putting my life in Chaka’s hands. I didn’t have no lawyers of my own. But that’s my own fault.”

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It’s the beginning of October, five months since Chingy first sat down with XXL to discuss his story. Chilling with a couple of Coronas at a long wooden table in a photography studio in central Chicago, the hip-pop star is clearly more confident than he was back in May. Having finished up work on Powerballin’ he’s eagerly awaiting its release, scheduled for November. The first single, “Balla Baby,” has already hit the airwaves to positive response.

Chingy’s in Chi-town for a stop on a monthlong promo tour. He and his crew, the Git It Boyz—Boozie, Rich Money, Wahone, DJ Sno and Chingy’s brother O.G., the first artists signed to Slot-O-Lot—did an on-air interview with Power 92 WPWX last night. This afternoon, the budding CEO’s lanky body is draped in a custom-made, super-sized T-shirt emblazoned with the phrase: I Trust Me—his new personal daily affirmation, he explains. “Trust yourself,” he says. “Ain’t nobody gonna look out for you like you. Ain’t nobody going to help you like you help yourself. And don’t put all your trust into nobody else.”

In February 2004, Disturbing Tha Peace went on a five-week tour in support of Ludacris’ latest album, Chicken-N-Beer. It was while he was out on the road, Chingy says, that he first got the idea that his management situation wasn’t kosher. “While on the tour, I had already sold two million records,” Chingy says. “And I was getting $10,000 a show. If I do my own shows, I’d be getting $30,000, $40,000, so it was weird... At the end of the tour, I was like, Damn, how can I make, like, $30,000 or more doing shows by myself and not make at least that much when I’m on the tour? Then with the merchandise on the tour—me and the Trak Starz were supposed to split the merchandise 50-50. I didn’t know that certain other people were getting a cut of the merchandise money too... I didn’t know what I was making off the merchandise and what I was losing.”

There were other issues: “I do a song for somebody, that could be for $80,000, no management contract here. They [EbonySon] wanted to take 75 of that, or 70 and give me 10. One time I did a song with a particular person and they had told me that it was for this amount of money, and from what I heard from the management it was for this amount of money [thousands less]. So I was confused... Then people would come up to me and tell me about things that they wanted to work with me on. I didn’t know nothing about it. I wasn’t getting told...”

Chaka Zulu maintains that he repeatedly encouraged Chingy to find separate management, but Chingy insisted on having him handle his business affairs. “He said, ‘No. I want you to manage me.’” Chaka says. “So I said, ‘Okay, cool.’ And we didn’t do no paperwork, but he knew the terms: if I manage you, I get 20 percent from any monies I earn you... This is the reason I didn’t want to do a contract: ’cause I didn’t want him to feel obligated to be with me.”

Chaka defends the per-show payment as standard for a consistent run of smaller venues (House of Blues, etc.) during a traditionally slow time of year, and points out that other artists took pay cuts for the tour as well. Neither EbonySon nor DTP received any money from Chingy merchandise, he says, and he insists he made the best decisions possible about who Chingy recorded with, and that Chingy was paid in full for everything he did. “All his money got paid to him,” Chaka says. “And all that stuff was proven when he switched accountants and lawyers and all of that and they did audits. Ain’t no money missing, period.

After the tour wrapped, Chingy hired a lawyer and drafted a letter expressing his desire to sever all business ties to EbonySon Entertainment and DTP. While he says he’s still cool with Ludacris and the DTP artists, he hasn’t spoken to Chaka Zulu since. Chaka says that, technically, Chingy is still signed to DTP as an artist, and whether or not the company’s logo will appear on Powerballin’ is “something that has to be discussed.” Chingy’s lawyer, Eric Kayira, has a different take, offering a carefully worded statement: “1) On album one, Chingy was a Disturbing Tha Peace and Capitol Records artist. 2) Presently, Chingy is a Capitol Records artist and is no longer connected to Disturbing Tha Peace Records. 3) Chingy continues to have a positive and strong relationship, legally and personally, with the Trak Stars. And 4) The parties remain amicable and Chingy simply finds himself at a point of growth where he has now an independent relationship with the support of Capitol Records company.

Steadfast in his decision to leave DTP, Chingy is still loath to lash out. He looks at the situation he’s emerging from as a learning experience. It was his own naivete that got him burned, he says; his own fault. “You leave the gate open for somebody to come and get your dog, they gonna come and get your dog if they want your dog. But I can’t blame anyone. I didn’t have a lawyer or an accountant. I’m knowing now that you’re not supposed to have a manager or accountant that works for the record company... If I had a lawyer, he would’ve got to the bottom of it. He would’ve already been involved and it would’ve already got fixed. I ain’t really gonna blame nobody and I really ain’t gonna blame myself. ’Cause as a young guy coming into it, not knowing nothing, I’m just happy to be doing it. I didn’t have a lawyer, I had no representation, none... Yes, there’s a right and a wrong way to do things, but I felt like nobody’s gonna do nothing to me because I ain’t did nothing to nobody. You can’t point fingers or blame anyone, because I went into the situation wrong. I learned a lot from them. There’s no bad blood.”

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However the legal situation plays itself out, it’s understandable to think that Chingy would want to disengage himself from DTP. It’s standard practice these days for successful rappers to have their own labels, and it must have felt a little weird to have Jackpot, his first album, outsell his boss’ fourth one, Chicken-N-Beer. “I always wanted to be my own man,” Chingy says. “I didn’t want it to be looked at as ‘Ludacris’ and then ‘Chingy.’ I wanted it to be ‘Chingy.’ I thought about it like, I’m fittin’ to go and stand up for me and do what I gotta do. Luda’s already established. I was under his wing. Even if I didn’t want to look at it like that, that’s how it was looking.

“I needed time to think about my next move and wanted to take everything into my own hands,” he continues. “Plus I got the Git It Boyz, and I was trying to get them on. DTP was saying, ‘Yeah, the Git It Boyz,’ this-and-that, but they wasn’t showing nothing. They was just being my hypemen on stage and I wanted to be bigger than that. I wanna be more of an entrepreneur.”

Sure enough, the Git It Boyz are prominently featured on the new album. They’ll have to fight for shine, though, on a track list that boasts some mighty powerful guest-star power. “I am using more people, bigger guest appearances, ” says Chingy, of Powerballin’ collabos with top-billers like R. Kelly and Janet Jackson. Strange company, perhaps, for fellow cameos like Dirty South legend Bun B, Lil Wayne and Nate Dogg. “I had to get a little more street on this one, ’cause the first album, it was more party. This one, I’m keeping it fun, but I did those street cuts. I also have more to say on this album. I been through more.”

Most recently, Chingy’s been going through an increasingly common rite of passage in the rap game. In support of local business, he says, he went out and bought Nelly’s new album, Sweat, as soon as it hit stores. He was grooving to the music, diggin’ the beats, when suddenly, on track nine, a song called
“Another One,” he hears his own words coming right back at his chin. “He said, ‘I like it when you did that right thurr,’” Chingy recites. “Just remember why you do that right thurr. I made it tight to be country...’ That’s false. That’s not true. I understand and I appreciate what he doing, and he did open doors for St. Louis, for us getting in the industry. But I been rapping just as long as dude, flat out. So by Nelly saying that... I just feel like he shouldn’t have said that. Why put me in that category when you said that? In a category like I didn’t do anything on my own? He was threatened by me and I felt disrespected by that because I never said nothing to dude. How you gonna feel threatened when you got millions and millions, and you sold millions of records? Do you and let me do me.

“I ain’t trying to get in no problems with anyone,” he continues, insisting that he won’t be slapping back at Nelly on wax. “But at the same time, I’m a man, and if you talk about me, I’ma respond. But I ain’t into manufacturing the beef stuff. If we got a problem then you need to holla at me and we’ll handle it like that. I’m not into going back and forth on record.”

Chingy’s not about holding grudges. He’s just too nice for that. Some might say, in fact, that he’s just too nice, period. In a rap world that feeds off drama and tension, his laidback, have-fun-and-feel-good style rubs a certain segment of the audience—the heads, the hardcore, the purists, the connoisseurs—the wrong way. (Coincidentally, or maybe not, Nelly suffers the same problem.) Of course, it’s not the worst problem to have—and sales figures prove Chingy deserves the title of rap star. He does, after all, move the crowd—in the direction of the record store. The kid came out of the Midwest with no prior mixtape exposure, no big push from his crew, and he got millions of people to go out and buy his album. And he didn’t have to diss anyone to do it.

“I’m a rapper,” Chingy explains simply. “I rap about some things that I done been through, seen, wanna do, trying to do in life... I ain’t trying to be no threatening person in the game. I’m trying to do this and make money and put out good music. My music makes me feel good. I don’t want to feel bad. I want to be happy.”

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