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There’s a party going on right here. Fresh from rocking a crowd of 13,500 at the Nikon at Jones Beach Theater in Long Island, NY, Wiz Khalifa is unwinding in his dressing room. The sold out show was the latest stop on the Under the Influence of Music Tour. It’s midnight, all the beer is gone, and the strategically placed incense sticks have all burned out. But a bunch of people are still floating around, as are an endless supply of joints, plastic red cups filled with Bombay gin and lemonade, and the sounds of classic hip-hop breaks and beats.

It’s all fun and games as Wiz—who’s been rocking the same torn-up, skintight jeans for three days—kicks it with his inner circle.

There are Taylor Gang members Tuki Carter, Wiz’s personal tattoo artist, and Berner, the aptly named weed guy who’s working with Wiz on a clothing line called Freshko. He’s also famous for his web video series, “Stoner Girls Gone Wild.”

There’s Chevy Woods, Wiz’s longtime friend and trusty sidekick. There’s Benjy Grinberg, founder and CEO of Pittsburgh rap powerhouse Rostrum Records. It’s been a busy day for Benjy since both of the tour’s headliners, Wiz and Mac Miller, are signed to Rostrum.

Then there’s Brian Brick, owner of the clothing store Timebomb, a staple of Pittsburgh hip-hop and one of the first places to sell Rocawear, Phat Farm, and Ecko in the City of Steel. There’s a little bit of all of them in Wiz, who is, after all, a fully tatted stoner rapper entrepreneur whose come-up put Pittsburgh hip-hop on the map.

Brick and Wiz are discussing one of Wiz’s favorite groups, Three 6 Mafia. “There are kids these days who don’t even know Juicy J’s old shit,” says Wiz. “Before, Juicy was cadences, he’s more lyrical now.” Though he’s down with the Taylor Gang, Juicy’s headlining the Smokers Club Tour today. But an unexpected guest has come by to hang out: J. Cole.

Wiz has known the Roc Nation rapper for years. “We met in the streets when we were both out thugging,” says Wiz. “We ain’t have no money and no deal. We rose in our situations together. We share a lot of the same experiences.”

Those would be the experiences shared by all newly minted rap stars—the delicate balancing act of chasing chart success while maintaining underground respect. And make no mistake, whether you prefer his crossover hits or his harder mixtape cuts, 24-year-old Cameron Jibril Thomaz is by all means a star. He’s got the Billboard hits, the plaques, and the national tour to prove it. More important, Wiz has done what so many young spitters dream of, but only a select few actually pull off: He’s evolved from local star to indie signee to Internet celebrity to major-label superstar.

These days Wiz is Uncle Snoop’s favorite nephew. He’s the only one in the industry Kanye West respects. And in Wiz’s own terms, he is the O.N.I.F.C. (Only Nigga in First Class). Watching him balance work and play, juggle commercial expectations and creative vision—all while maintaining relationships with fans and friends alike—is an object lesson in the trials and tribulations of rap stardom circa 2012.

But right now, he’s just having fun playing a game with Cole. The game revolves around identifying the samples behind classic rap records like the Charmels’ “As Long as I’ve Got You” (sampled on Wu-Tang Clan’s “C.R.E.A.M.”), Bobby Caldwell’s “My Flame” (Biggie’s “Sky’s the Limit”), and the Five Stairsteps’ “O-o-h Child” (2Pac’s “Keep Ya Head Up”), all of which are bumping through a Bose speaker dock from a playlist on Wiz’s iPhone.

Guests around the room have to name the rap record that used that particular sample. If they get it wrong, they have to guzzle a shot from a one-liter bottle of Bombay. If they get it right, whoever asked the question takes the shot.

“Who’s the white boy that doesn’t know this sh*t?” asks J. Cole, of no one in particular.

One white boy who would probably recognize all the samples (but has no time to play because he’s too busy recording on his tour bus) is Wiz’s labelmate, Mac Miller. The Pittsburgh mixtape sensation, whose indie releaseBlue Slide Park debuted at No. 1 on the Billboard albums chart last year, was recently sued for $10 million by Lord Finesse over a 2010 mixtape cut. It seems the Diggin’ in the Crates Crew wasn’t cool with Mac diggin’ intheir crates.

“The game has changed,” Wiz says. “Not to say anything against Mac, but to any artist [who wants to] make their situation stronger, make sure the songs that you publish sell more than your mixtape stuff. That will help you stand up against that because nobody can say that you’re building your career off it.”

Wiz ought to know; he’s built quite a career himself. Hits like the Stargate-produced smash “Black & Yellow” and the Benny Blanco–produced follow-up “No Sleep” have raised him to the top of the rap game. Still, the hustle never stops. One of the two huge Prevost tour buses parked outside contains a makeshift recording studio. He’s come a long way since the days when he rolled back and forth from Pittsburgh to New York in Benjy’s black 1997 VW Jetta. He’s gone from performing in front of 20 people to averaging 20,000 a night, and from earning four figures a performance to six.

Midway through, Wiz and Cole’s sample game takes an unexpected detour as they start debating who knows the lyrics to Canibus’ “100 Bars” better. (To his credit, Cole can recite the first few bars of the song.) Later, when Cole describes a woman with a particularly fat ass, Wiz replies “I can’t even hear this man, I got a fiancée.” They play on into the wee hours of the morning, throwing back shots of gin until Cole winds up barfing in the bathroom while Wiz pats him on the back. It’s all part of the balancing act.

To read the rest of the cover story head over to Complex

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