Photography shot exclusively for XXL by Travis Shinn

Drama students are such precious little creatures. Grown-up problems like mortgage payments and job security are not yet a concern. Aspiring actors care deeply about their craft. And they are eager to learn. That’s why they have lined up outside of Pace University’s Michael Schimmel Center, in Lower Manhattan, for a taping of Bravo’s Inside the Actors Studio. Tonight they will hear from a real pro.

Backstage, the program’s thespian star of the night skips up a side staircase, turns the corner and strides down the corridor toward his dressing room. He’s wearing a tailored navy-blue suit, a black T-shirt, black Nike sneakers and a pinky ring that’s visible from down the hall. The greenroom, filled with a congregation of lawyers, managers, record executives, A&Rs, publicists, assistants and production assistants, empties. Some folks just loiter in the hallway. Most make their way into the dressing room to get closer to the night’s guest.

Inside the Actors Studio is a show where actors are interviewed in front of an audience of drama students. It’s been on for 16 seasons, is seen in over 125 countries and has featured some of the biggest names as guests, including Al Pacino, Johnny Depp, Robert De Niro, Angelina Jolie, Will Smith and the evening’s interview subject, Sean “Diddy” Combs.

The rapper and major music mogul has starred in two feature films (Monster’s Ball and Made), one Broadway play turned TV movie (A Raisin in the Sun) and one direct-to-DVD sequel (Carlito’s Way: Rise to Power). Tonight he’s here to plug his latest film, Get Him to the Greek, a raucous comedy co-starring Russell Brand and Jonah Hill, set for release this month. He plays Sergio Roma, a savantlike record executive known for his hit records and loud mouth. Sound familiar?

The two-hour interview with James Lipton, the program’s oft-parodied 83-year-old host, goes smoothly. The guest talks about his childhood and his long, storied history in the music industry, starting as Puff Daddy, up to Diddy. (Although he’s gone through several official name changes—P. Diddy in 2001, Diddy in 2005—it seems he’ll always be Puffy or Puff to most fans and folks around him.) He beat-boxed as Lipton jokingly freestyled. He even reluctantly rose from his chair and Diddy-bopped. He also spent very little time actually talking about acting. In fact, the subject wasn’t broached until 80 minutes into their chat. Still, Lipton thinks Puff was worthy of a visit to Inside the Actors Studio.

After the taping, Diddy’s dressing room is calm. His mother, Janice Combs, sits quietly. His good friend, the unsigned rapper Jay Electronica shows off his iPad, while Diddy’s artist Cassie gets half of her head shaped up by a barber. Meanwhile, Diddy huddles with his manager, Chris Lighty of Violator Management, and co-manager James Cruz. “He went in,” Puffy says about Lipton’s methodical and agonizingly obsequious interview. “It was surreal for me to be on Inside the Actors Studio. It was surreal for me to be on that stage.”

Even Puff seems amazed to have scored this gig. And by now he should be used to winning.

After all, Sean Combs is the most successful entrepreneur to emerge from hip-hop. He surpassed Russell Simmons back in the 1990s, when the Def Jam co-founder backed away from the music industry. Even his contemporaries, booming businessmen such as Jay-Z and 50 Cent, either lag behind or travel down a road Diddy paved. His label, Bad Boy Records, set the precedent for Roc-A-Fella’s and G-Unit’s partnerships with Def Jam (1997) and Interscope (2003), respectively, when the boutique label signed a deal with Arista/BMG back in 1993.

He was a 360 artist before the term even existed—his business was founded on hip-hop but not limited to it. “Diddy is someone who taught young artists how to turn hip-hop into an industry,” says Jimmy Iovine, chairman of Interscope Geffen A&M, where Diddy is now signed as a solo artist, and Bad Boy is signed as a label. Under the terms of the deal, any new artist signed to Bad Boy will be distributed through Interscope, while currently signed artists (and the Bad Boy catalog) will go through Atlantic Records, where Diddy signed a deal in 2005. Besides being an entertainer, he’s a businessman. His vast empire includes Bad Boy Worldwide Entertainment Group, Sean John Clothing, Inc., Blue Flame marketing, which has counted Pepsi and Hewlett Packard as clients, and Justin Combs Publishing, which houses the songwriting credits of artists like The L.O.X. and 112. The latest, non-musical business deal, however, is with the Diageo liquor company. In 2007, Diddy entered an equal-share venture with Diageo to spearhead Cîroc vodka’s brand management. It’s been a fruitful partnership. In the second half of 2007, Diageo shipped 60,000 cases of Cîroc worldwide. That number jumped to 400,000 cases for 2008–2009.

All told, Puffy’s unconfirmed net worth is reportedly more than $350 million. It’s quite a résumé. And he knows it. “I am the champion of hip-hop,” he says. “Hands down, undisputed, I’m the undisputed heavyweight champion of hip-hop.”

It’s a week after the Inside the Actors Studio taping, and Diddy sits in Los Angeles’ Paramount Recording Studios. “We are going to have to deal with those facts. There is nobody that can fuck with me with what I do, which is getting busy. We are going across the board, as an entrepreneur, innovator, motivator. Who was there first? Who traveled to Europe first? The first. The first. The first. The first. I was the first.”

He lets the words hang in the air. “I was the first on the jet. I was the first running the marathon. I was the first donating millions of dollars. I was the first. I was the first with the 10 million records sold. I was the first with the label. I was the first with the renegotiations. Fuck a Forbes list—I was on the cover of Forbes. There is going to be someone that will pass me, but as long as I’m on the court, they are not going to be badder than me, because there is too much catching up to do…There is not one muthafucka that’s here now who is going to outwork me. That is not going to happen, not right now. Maybe if I slow down, but to this day, no one can fuck with me when it comes to getting busy and working.” —Thomas Golianopoulos

To read the full Diddy cover story be sure to pick up the June issue of XXL, which is on stands now!!!