Can rap be funny? Can a funnyman rap? And just what the hell is Rick Ross smiling about? We hit the beach with the Bawse and Andy Samberg to find out. It’s going to be a hot summer.

By now you’ve seen a few sides to William Roberts, better known to the world as Rick Ross. There’s the corrections officer smiling awkwardly in a grainy photo; there’s also the mogul-in-the-making who calls the shots for his newly minted Maybach Music Group imprint. And, of course, there’s the heavy-set rapper who spits pitch-perfect coke rhymes and makes everyone forget the C.O. and eagerly anticipate what the mogul might do with an army behind him. Yup, we’ve all seen those sides to Rick Ross, but we’ve never seen the humorous, witty “character” whose personality is as large as his waist-line. Until now. Rap critics, feel free to call him a character, ’cause that’s what he is—a character who cracks jokes, takes off his shirt faster than the girls at Sue’s Rendezvous, and is totally comfortable in his own heavily tatted skin.

We’d like to take all the credit for bringing out Ross’ comedic side, but that nod goes to Saturday Night Live funnyman Andy Samberg. The 32-year-old comic vet whose television skits turned viral videos (“Dick in a Box,” “Lazy Sunday”) have racked up more views than “2 Girls 1 Cup” is slowly solidifying his place as an SNL legend. You may scoff at the thought of a gangster rapper and a parody rapper sharing the same stage (or the same cash wave for that matter), but the connection isn’t too far-fetched when you’re dealing with two people who are into setting up their crews for success. At the height of Maybach Music and Lonely Island hype, Ross and Andy bonded over dick jokes, dissing comedians, and drug-lord nicknames. Just let it be known, if these two guys ever pop up on an SNL digital short together, we’re coming for the check, Lorne.

Both of you have new albums. Andy, what’s the science behind Turtleneck & Chain?
Andy Samberg: Songs about our dicks, fake rap, and other fake music.

Rick, you have God Forgives, I Don’t. What’s the direction with that?
Rick Ross: It’s beautifully violent. It’s street music at its finest.

Beautiful violence and penises. Your marketing departments must love you. Do you guys expect any other similarities out of your respective albums?
A: They’re both going to come out. [Laughter.] They’ll definitely both be available on iTunes. CD. In the future we’re going to get them out on laser disc.
R: Fuck, yeah!

Rick, can we expect some dick jokes on God Forgives, I Don’t?
R: There will be a few “suck my dick” and blow job mentions here and there.

Already you’re making a connection.
A: Rick, did you ever see the biopic on Don King? My favorite line from that is when he’s in the bathroom talking to a dude while he’s taking a piss and the guy asks, “Hey Don, aren’t you going to wash your hands?” and he’s like, “Shit, I wash my hands before I touch my dick!” 
R: [Laughs.] That’s true, though.

When did you both decide that you wanted to be rappers?

My favorite line from the Don King biopic is when he’s in the bathroom, and he’s like, ‘Sh*t, I wash my hands before I touch my d*ck!’   —Andy

A: I’m a comedian, and I decided I wanted to be a comedian when I was eight years old watching old Saturday Night Live episodes. I never decided to be a rapper because I’m not a rapper.
R: But he hangs with cool-ass rappers.
A: I’ve been lucky enough to chill out with rappers because of my love for rap music.

What about you, Rick?
R: Hanging out at an arcade and they had a big-ass screen on the wall. Some fine chicks walked in and they had biker shorts on. I was in fourth or fifth grade at the time, and I was like, “Damn, these are the finest chicks I’ve ever seen.” I just saw the way they reacted to Big Daddy Kane when “The Symphony” came on. I started doing the flattop right there. [Laughter.]

Rick, is there anyone you don’t fuck with comedically?
R: I fuck with my homie right here. We don’t fuck with Carrot Top. 
A: I don’t think I would step to Carrot Top, though—he’s jacked as hell. [Laughter.]

But maybe if you were rolling with the Bawse…?
R: He’s got the Bawse with him now.
A: That’s true, yeah, I’d go at it.
R: Yeah, we said it. Fuck Carrot Top!

Andy, who’s the softest dude in rap?
A: I’m not really in a position to call anyone in rap soft. Probably me.

Rick, if you got into acting, what kind of role would you play?
R: “The Weed Head.” The Bawse weed head. Testing the strains that I got my team growing for me. That’s what I do, I count the money and I test the product. Read more…