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How Andy Milonakis Went from Having an MTV Show to Rapping with Chief Keef

Andy Milonakis dishes on his surprising second career as a rapper.

Andy Milonakis and Glo Gang. Picture via artist's SoundCloud

Once upon a time, back when I was a wee teen working at the mall, I made friends with a very nice man named Andy Milonakis whose show I’d grown up watching on MTV. At the time, we were both surfing waves of viral hip-hop stardom (mine, admittedly, far more fleeting), and he would give me advice on coping with my new plague of Twitter haters. In fact, it was Andy himself who dubbed me the Rap Game Taylor Swift.


Since those fateful days, Andy Milonakis, already a legendary MTV comedian-turned-YouTuber, has expanded his horizons to include rapping, directing, and talking about food on Twitter. I sat down with him to discuss exactly what the fuck he’s up to after Chief Keef and Gucci Mane dropped mixtapes this week, both featuring Andy Milonakis himself.

Noisey: So you worked with Gucci Mane and Chief Keef?
Andy Milonakis: It’s real, man. The Chief Keef mixtape came out two days ago. I actually didn’t know the Gucci thing was gonna come out already—I thought it would drop in like, six months or something. I knew the date of the Chief Keef mixtape was the 17th, but when I woke up and logged on Twitter, I started getting all these tweets about Gucci Mane. Apparently Gucci’s mixtape dropped the same day… it was a pretty good day for a white boy.

How did that even come to be?
Well I was talking to Chief Keef a couple of months ago, like let’s hang or whatever. Nothing came out of it, we talked about hanging but it never happened. A while later, I unfollowed every single person on Vine because I got so mad about how shitty Vine comedy was, and he hit me up like, “I know you’re not following anyone on Vine and I think it would be funny if you just only followed me.” Two months later, he tweeted at me to come hang out and we ended up exchanging numbers again. We didn’t plan on making music; I’m not really pushy about that stuff. One thing I really hate about the Hollywood shit is when people are really pushy about working on things together. Anyway, he invited me to his house. I called an Uber, and it was so fitting; a big fucking matte black SUV picked me up. I was like damn, do they know I’m going to Chief Keef’s house? I was feeling the rap vibe and had a couple of ounces of (lean) left and I hadn’t drank lean in like a year, so I stopped at this Chinese restaurant on the way to get Sprite and drank lean on the way to his house. We hung out and listened to like 100 beats. He was in the process of making a studio out of his guest house so there was no microphone, but after a while one of his boys was like, “Fuck listening to all these beats, we need a mic,” so we decided to get a studio right then. I called a bunch of studios and we ended up at this studio in Burbank, and I wasn’t even planning on laying anything down but he was texting me from the booth, “Yo, you got something for this? You gonna come lay something down?” I was like, “Oh shit, I didn’t know I was supposed to be writing.” So I wrote a verse, laid it down, and he just kept hitting me up like that for every beat that came on. I ended up writing six songs with him that day. It’s cool because he really wants to do shit with me, and I fuck with him, so I think its smart to do it. It helps me a lot, but I feel like it’s also cool for him because his fans are kind of shocked in a good way.


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What about Gucci?
I wrote a verse and recorded it with Gucci Mane’s engineer. I honestly didn’t know I was on a Gucci track until after the song was done. Fredo Santana, Chief Keef’s cousin, heard the song and was like, “Yo, I’m gonna hit Gucci up and tell him you’re on a song.” Of course, as a white boy that kinda raps part time, I’m thinking, “Oh no, he’s gonna be like ‘fuck that cracker’ and take me off the song.” But he didn’t, and like a week later I was on his mixtape.

I would be dying.
Yeah it’s pretty sick. It’s weird because I’ve been doing it a long time and it’s kinda hard to break through when you’re seen as a funny white boy who raps sometimes. Rappers take shit so seriously sometimes, they’re like “That’s lame, that’s hokey, that’s not my vibe.” It’s cool to fuck with these real heads, people who are respected. Plus, it opens doors to work with more people. Once you break that barrier, it’s easier. With Riff Raff, too; he did a bunch of shit and big rappers weren’t fucking with him in the beginning, but he kinda penetrated through. Then it wasn’t like, “He’s joking”—it was like “Yo, he’s jokey, but I’ll work with him too.”

Does that mean this is the end of Three Loco?
It’s already been the end of Three Loco.

Can you tell me what happened when y’all made “We Are Farmers?”
I was watching TV and that Farmers Insurance commercial came on, and I was like “Yo, that fucking thing is so catchy. That would be so fucking hard as a beat.” I showed it to Diplo and he had DJA turn it into a beat in like, ten minutes. We put it out, and within 24 hours we had a cease and desist letter. I could have picked any obscure sample, but of course I had to pick one of the biggest insurance companies in the world and steal their melody. Obviously we were signed to Mad Decent at the time, but if I wasn’t on a label I would have just been like, “Suck my dick. What are you gonna do bitch? Take me to court. Like fucking, Rocky V. ‘WHAT ARE YOU GONNA SUE ME FOR? SUE ME FOR NOTHIN?’” But yeah, I would’ve told them to eat a fat dick if we weren’t signed but we had to take it down and put a fake version on the EP. That beat sucks compared to the real one.


There’s really never going to be a Three Loco reunion?
I mean, who knows. We might do a couple songs or videos down the line. I was kind of pissed at Riff, we had a little beef for a while, but I talked to him. (Three Loco) had had some deals on the line; not just for an album, but for an independent movie and some other stuff. In the end, it came down to us all disagreeing on what was best for us. I’d always watch that show, Behind the Music or whatever? I’d hear about all the drama that bands go through and think, wow, it must fucking suck to be in a band. There’s so much drama and so much bullshit. Our shit wasn’t that extreme; we had one album, we didn’t do that much. We did a lot of shows for like, one year. It wasn’t drama the whole time, but I don’t really like relying on other people. I just like doing my own thing.

I don’t really fuck with other people like that.
It’s too much. I have a very comfortable drama-free bubble that I live in and sometimes drama comes my way, but I’m good at keeping it out. Drama is not a comfortable way to live. It’s not healthy, mentally, to live like that.

You’re always getting in Twitter beefs, though.
Yeah, but 99 percent of them are fake. Which one are you talking about?

I dunno, I always see people talking shit to you on Twitter. What’s the funniest one you can think of? I like asking this because people are constantly talking shit to me on Twitter.
I ALWAYS have people talking shit to me on twitter… I can’t even think of a funny one. Today someone told me I look like Amy Schumer. I can’t even think of a funny one because the people who are actually funny and creative use their humor for more constructive things than shit-talking on Twitter. Nobody who’s talking shit on Twitter has anything funny to say.

So what’s the next thing you’re working on?
Well, me and Chief Keef are gonna do a video, I have a meeting about that in a couple of hours. I wanna it to be this green screen space adventure. I’m also developing a new comedy show, mainly for my YouTube… I wanna focus more on my YouTube channel this year. It’s gonna be like an “Andy Milonakis Show: 2.0” type of thing. This rap shit’s fun, but I really feel like it would be cool to go back to my comedy roots and make people laugh again. People leave comments and write to me telling me that they miss that type of stuff, so I’m gonna make a brand new show. It’ll be some sketch comedy, man on the street stuff, I’m gonna throw some music in.

I want in on that. You better hit me up about that.
Alright. I’m gonna turn you into a lil cartoon raccoon. We’ll have you digging in a little cartoon garbage.

Kitty Pryde raps and writes and tweets in Los Angeles. Follow her on Twitter.