Was playing a role so deferential to authority a challenge then?

KC: It was exciting. I would never be an assistant, let alone for someone as powerful as Ari Gold. But being someone else for a little bit, exploring someone else’s world? I might not have done it in my own life, but I thought it was interesting for the character to develop something. Even though he may not have had a lot on the page. And thank God for Jeremy, who matched me on that. He could’ve improv’d some shit. Most people see Kid Cudi the all-powerful on stage, the mighty “I Answer To No One” Cudi. It’s just cool to play this little, timid character.

JP: That’s what acting’s about: taking on roles that have different status. In this country, people fall prey to profiling you. You even felt it from those—who shall remain nameless—who said: “Cudi’s too cool. He can’t play that role.”

Right. In the music world, Cudi doesn’t take orders, but he played someone reacting to higher status in the movie. Do you prefer playing characters in positions of power, Jeremy?

JP: I actually play better reacting off lower status than higher status. The irony with Entourage is that Ari Gold was the smallest character on the pilot. I was in one scene. At the time, I was being offered leads, but this show came along, and I was fascinated by it.

Why?

JP: Because the backstage life of Hollywood is Shakespearean. It’s such a great, fertile premise. I needed to do it. I knew who Ari Emanuel was, so I knew that there was a great prototype for this character. I thought, HBO is the place to be. You get street cred from the jump. If you could get in there, put your ego aside, and forget about where you think you should be and play this small role, there’s a lot there. My first 40 movies, I was playing small roles, and seeing a way to make them bigger. I was always the underdog. And by the way: once the underdog, always the underdog.

KC: I agree.

JP: If you’re hungry, you’re going to stay hungry. Not everyone is like that.

KC: I’m like that for sure. [Pauses.] When’s your birthday?

JP: July 26.

KC: Hmm. I’m in January, but was wondering...

JP: This is like Match.com. [Laughs.] You know who else’s birthday was July 26? Mick Jagger, Kevin Spacey...

KC: —Christian Bale. Ten years apart, exact same day, he’s 1974 and I’m 1984. But he’s intense. He’s fucking Batman, bro.

You represent two different generations in Hollywood. Cudi’s getting in now and, Jeremy, you’ve already experienced so much. What do you think the biggest difference is between your Hollywood and his?

JP: We’ve definitely come up in different times. I’ve never experienced a weirder time to be famous. I think it’s never been less cool to be famous than right now, because you’ve got a group of people, and you don’t know what they contribute. Yet they’re taking victory laps; they may be acting out on reality shows. Throwing breast milk at each other, making a great deal of money. So that’s awkward, and strange. There’s a lot of attention being paid to that, and people getting shots for reasons other than...

KC: —artistry.

JP: I came up in a time where you could do a lot of things under the radar. Now, everything is documented. Cudi’s different froms the rest of the people in this generation, because he really can be humble. He’s willing to learn, and grow, and get better. A lot of people of this generation don’t have that patience. They want to blow up now.

KC: Like, right now. I hate that.

JP: They want a shortcut. The reality is there are rites of passage.

For example?

JP: I won the “Fresh Face of the Year” award at 37. My face was not fucking fresh. They were like, “He’s an overnight sensation!” It took me a long time for my career to come to fruition. I don’t know if there’s a lot of patience anymore. I think that could serve a lot of people.

KC: There’s a truth in that.

Specifically?

KC: If I wanted to get my music in anybody’s hands, I had to run into a motherfucker. Face-to-face. And I’d better have had a CD—a big-ass, bulky CD—on me to hand to them, so they could hear my music.

Which is so different from how the music industry works today.

KC: Nowadays, anyone can make some shit in their room. It’s easy to make shit. You don’t even need a keyboard now. People make beats, become an artist overnight, and it’s like, “Where’s the hard work?” I remember me and Dot Da Genius sitting for hours, me being on him about the mix for “Day ’n’ Nite,” being like, “It’s not right. We want people to take us seriously.” We listened to Dr. Dre’s beats. We listened to Timbaland’s kicks and drums. Kanye shit—we needed to sound as professional as that. We didn’t have shit, but we approached it with professionalism. I approached it like, “We have to be over-the-top good.” I don’t think kids have that nowadays. They just throw some shit out there, throw some auto-tune on it, like, “I don’t need anybody to tell me if I’m in key. I don’t need anybody with me that has any musical ear at all.”

JP: But the music industry, isn’t it breeding that?

KC: Yeah. But for me, it works. Like, yes, keep doing all the shit you guys are doing, because all I’m going to do is the right thing, and I’m going to end up looking like the genius. Just doing what I’m supposed to do. Fucking making music. Playing the drums or playing the bass. And I hate playing the bass, bro. I’ve been playing the bass because it’s there and I don’t want anyone else to play it. I also feel like I’m at the tail end of an era. I’m the oldest. Me and J. Cole.

JP: How many years have you been making music?

KC: Six or seven years now. “Day ’n’ Nite” came out in 2007. 808s and Heartbreak was 2008. Those were my first credits.

JP: But before that, how long were you making music?

KC: Since I was 15.

JP: OK, so, for 15 years.

KC: Five years before I moved to New York, I was making music, so that’s what I’m saying. For 10 years, I had time to suck. Nobody got a chance to critique me. Pitchfork didn’t have a chance to hear 19-year-old Scott and rip him to shreds, and shit on his heart. They do that now to the grown Scott, but I’m confident in my art, so it doesn’t really matter.

JP: People need to know you have to walk through that rejection, and it’s only going to fuel you. If you can somehow look at it like it’s a gift, you’re just going to regroup, and work harder, and go deeper. So just embrace it.

KC: If you have that in you to win, it’s just learning. It’s just growing pains.