Simon Rex Is Winging It

The multi-hyphenate “Scary Movie” star discusses luck, living without a plan, and breaking up with weed.
Simon Rex Is Winging It
Courtesy of Henk Steyn Photography

In a strong deviation from his previous work, Simon Rex—aka Dirty Nasty—confides he’s recently completed a kid’s album. “I’ve done all the music I could do about getting my dick sucked and doing coke, so I thought, let me flip things on their head and do a kid’s album. I thought it would be hilarious.” Littered with good morals and cute music, the record was recently purchased by a cartoon animation company, which is currently in the throes of animating the project to life.

Over the course our lighthearted phone conversation, Simon reflects upon his early years as a model, his breakout as an MTV VJ, his ensuing success as an actor, a respected foray into rapping/producing, returning to interviews via his podcast, “Nervous Rex,” and his continued journey following new and different paths.

Growing up, did you always have a funny perspective on life?

Simon Rex: I grew up an only child in the 80’s in San Francisco around a bunch of weirdos. My mom was a hippie and she told me the other day she would make me sit in my room for an hour so I could learn how to be alone. Being alone is what made me entertain myself and I think that’s where it all started.

When I was thirteen-years-old, I was on the jumbotron at an Oakland A’s game. I flipped-off the camera and thirty-thousand people laughed. I remember feeling, “Whoa. That’s fucking magic!” While I didn’t want to get into show business or anything, the [childhood] event must have planted a seed for me to entertain, because years later, the opportunity to do so fell into my lap in a fortuitous manner. I got really lucky. Right place, right time. Ultimately, I think [the funny perspective] came from being an only child.

And was being a VJ what firmly planted you in the entertainment business?

Simon Rex: Again, that was total luck. I was dating this girl while working at a potato sack factory in Oakland. She was a pretty model who moved to Los Angeles and I ended up moving in with her. I started taking her around to auditions and one day, a casting director was like, “What’s up with your boyfriend?” She was like, “Oh he’s not a model.” And they were like, “Well, we want him for this job.” Next thing you know, I get this modeling job and I’m flown to Italy. I stayed in Italy, then moved to Paris and then to New York. So the modeling job was even lucky.

When I was in New York, my modeling agent sent me to MTV. They were interviewing a model and wanted someone to just bounce questions off of. So they sent me as a filler. I was never supposed to be on tv, they just wanted to know what they should ask a male model for this talk show. I made them laugh during the whole thing and they thought I was really funny. At the end they were like, “You wanna be a VJ?” I remember I said to them, “I have no journalism experience, I have no music experience and I’ve never been on tv.” They said, “Perfect.”

The [VJ] job fell into my lap just like modeling. Overnight, I was on tv everyday and everyone started recognizing me. This was back in the 90’s when there was no Internet or social media, so MTV was the only place you could go to see what was cool and what was going on in entertainment, music and sports. All of a sudden, everyone knew who I was. I was twenty-two-years-old or so and it was very weird. No one could ever prepare you for that. Then, [being a VJ] led to acting.

Gus Van Sant, the famous movie director, saw me on MTV and wanted to audition me for a movie. The movie was “Good Will Hunting.” I remember sitting across from Matt Damon and [Gus] handing me some lines. I start reading them with Matt but then [Gus] stops me. He goes, “Simon, I have to stop you. That was the worst audition I’ve ever seen.” I laughed, “Yeah, I’ve never done acting before. I don’t know what I’m doing.” He’s like, “It’s okay, you’re not ready to do this movie. But I’m going to send you to an acting coach.” So he sent me to this acting coach in New York and I started taking lessons and that’s how I got into acting. 

I never went for any of this, it all just fell right into my lap. Right place, right time, all the way. I never thought I’d be in show business. I was just a silly goose working in a potato sack factory and now, here I am.

There must have been some internal alignment with all of these opportunities that kept coming your way or else you wouldn’t have said “yes” to them.

Simon Rex: I think it was simply a matter of saying “yes.” A lot of people say “no.” The lesson is, “Just say ‘yes’ and go for it and see what happens.” I was never like, “No, I don’t think I should, I don’t think that’s the right idea, I see myself as something else.” I was always like, “Yeah, let’s try it.” You have to go outside your comfort zone and if it scares you, then do it. And that’s what I did. I would just do things like, “Fuck it, I’ll do that.” [And the process] worked. Try shit and see what works for you. I always just try and do different things, and at forty-five-years-old, I’m still trying to do different things.

You were open to whatever came your way and could see your path unfold while you were on it.

Simon Rex: I never thought about it like that. I wasn’t thinking, “Say ‘yes’ and go for it.” At the time, I did things because I didn’t know any better. As I’ve gotten older, I look back and realize I saw open windows and just jumped through. I was naïve. Everything happened without a plan.

I’m a big fan of not planning anything, which drives my mom and my friends nuts. I just want to go through life winging it. That’s when the magic happens. When you over-plan, you have expectations. And when you have expectations, you’re always let down. How dope is it when you don’t know anything about a movie, and you walk into the movie and it’s so good? But if you’d read 50 reviews beforehand, you’d be like, “Eh, it’s not what I thought it was going to be.”

Over-preparing for life takes the joy out of the journey.

Simon Rex: Totally, that’s the metaphor. Also, not trying too hard is another interesting conundrum. Like, “Don’t try.” The author Charles Bukowski left two words on his grave: “Don’t try.” At first, I didn’t know what he meant. You have to try, right? But now, I know what he means. If you walk into a job interview and you try too hard, people are going to be turned off. They’ll be like, “Eh, you wanted it too bad.” But if you don’t want it too bad, you’ll get it. If you’re hitting on a girl too hard, she’s going to be like, “Ugh, he’s trying too hard.” But if you just play it cool, she’ll be attracted to you. It’s kind of like the law of attraction. You don’t want to over-try.

Steph Curry, when he’s hitting threes, he’s not trying. He’s just in the zone. When Tiger Woods is golfing, he’s just in the zone. He’s not trying. He’s doing it. He put in the work to get to the point where he doesn’t have to try. So complex, yet so simple.

In terms of putting in the work, how did your music career start?

Simon Rex: When you’re a working actor, you have a lot of down time. If you work six months out of the year in Hollywood, that means you’re working more than 90 percent of people. It also means six months of down time.

I was working a lot when I first moved to Los Angeles around 1998. I was booking a bunch of movies and tv shows, but even then, I still had so much down time. I knew I was going to go nuts if I didn’t pick up a hobby. My friend from New York—Adrien Brody—of all people, taught me to make beats on a little drum machine. This was before he was the Oscar winning actor. We both were in LA, and when I’d go to his place, he’d be making beats on a drum machine. So I went and bought the same drum machine, this little Yamaha keyboard, and started teaching myself how to make beats.

Years later, after making beats as a hobby, my boy was like, “Yo, you should meet these dudes who rap—Mickey Avalon and Andre Legacy.” I was like, “I don’t want to meet any rappers, I’m just making beats for fun.” And they didn’t want to meet me. But my boy forced us to meet and we hit it off and started making music in my spare bedroom. This was like early 2000’s, back in the CD-burner days before the Internet really took off, and I would just burn CDs of me, Mickey and Andre fucking around rapping. I’d hand out [the CDs] to all these socialites and famous people in LA and they started burning the CDs and sharing them throughout Hollywood. Eventually, it just got out there that “Simon Rex has these rappers and the shit is dope.”

Mickey got signed to Interscope. Next thing you know, we’re opening for the Red Hot Chili Peppers touring through Europe in front of 70,000 people, and we’re just looking at each other like, “We were just fucking around in my spare bedroom.” Again, we weren’t trying. We weren’t like, “Yo, we’re going to make it in the record industry and blow up.” We were just having fun and it worked.

Interscope was like, “Okay, we loved what you guys did. Now do it again.” We looked at each other like, “We don’t even know what we did.” All of a sudden, there was a deadline and there were other people involved with their opinions, suits were involved, meetings with this person and that person, and the magic sort of went away. We’d recorded this album for Mickey with Dr. Luke, Katy Perry, Kid Rock, Kesha and all these big artists, but the album got shelved because it had lost the magic. [The album] was trying too hard.

Mickey got off Interscope and we went back to the basics. We still tour, but everyone wants to hear our old shit, like “My Dick.” The shit I made in my spare bedroom.

What’s next on the horizon for you musically?

Simon Rex: Me, Riff [Raff] and Andy [Milonakis] just put out a Three Loco song “Arrogant American Freestyle.” It’s one song that’s actually on Riff Raff’s new album, but we’re probably going to do more. I’m always working with Mickey on the road touring and we always put out a new EP every year. But I’d be lying if I said I’m still into rapping. I don’t feel like rapping anymore. I prefer to just make beats. That’s how I started, as a producer. I just bought a house out in Joshua Tree, so now I spend half my time out in the desert and half my time in Hollywood in the studio, and I’m getting back to just making beats for Mickey, Riff Raff, and Andy. I do it as a hobby, and sometimes the magic happens.

How is cannabis part of your life?

Simon Rex: I smoked weed all everyday from when I was in high school up until recently, but weed suddenly turned on me. And it had worked for me forever. Wake and bake, bong hits, spliffs, edibles, you name it, high all day. When I hit forty, my brain chemistry kind of changed. Instead of making me creative and motivated, weed made me paranoid and insecure. All the things people would say when I used to laugh and hand them the joint were now happening to me.

The other day I got high for the first time in a year. I ate an edible and went to see “1917” in the theater and had my mind blown because I was so baked. [The feeling] was great in the movie theater, but afterwards, I had to go eat dinner and had a mild panic attack. I was so paranoid. 

I’ve tried all the different strains. I’ve gotten the organic outdoor seven-percent THC weed. I’ve gone to the weed shop and been like, “Give me the worst weed you have,” and they’d be like, “Why would you want that?” I was like, “Trust me. I’ve been smoking weed twice as long as you’ve been alive. Give me your worst weed.” They’d give me their “worst,” but I’d still get all heady and stuffed up and tired. It sucks. It’s like my best friend and I broke up. I miss my best friend weed.

Follow @simonrex415 and check out his podcast Nervous Rex now streaming everywhere.

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