What The Hell Happened To Andy Milonakis?

Updated September 30, 2015 at 8:57 PM

A chubby kid sits on an office chair strumming a banjo. Based on the zebra-print blanket and unadorned walls behind him, he’s probably in a guest room of a family home. It’s unclear when he last brushed his hair.

“The Super Bowl is gay,” he sings, totally deadpan. “Super Bowl, Super Bowl, Super Bowl is gay.”

These are among the most complex lyrics of the song that follows, in which a variety of things -- including the Raiders and also water -- are declared “gay.”

“We thought [the] video was hilarious,” Jonathan Kimmel told The Huffington Post over the phone, recalling the absurd clip. “That’s before we knew we shouldn’t be saying those things, of course,” he added, now with mock sternness in his voice.

Another thing he didn’t know -- that Jonathan and his brother Jimmy Kimmel didn’t figure out until they managed to track that chubby kid down -- is that he wasn’t just a kid.

“I thought he was a child when I first saw him online,” Jimmy said. “When we contacted him, we were very surprised to find out he wasn’t.”

Andy Milonakis, now 39, was 26 at the time. He was working in IT, using his knowledge of computers to upload videos to a comedy website called Angry Naked Pat. He was also being charged massive overages for all the traffic his clips were getting because, well, that’s how the Internet worked in 2003.

If you were ever to call Andy Milonakis’ cell phone, you’d be transported back to the early aughts, thanks not only to the nostalgia of hearing his youthful voice but the reggae ringback tone that plays before he picks up.

“I guess ringback tones aren’t a thing anymore,” he explained. “I just really like reggae.”

Like the theme song that opened “The Andy Milonakis Show,” it’s a helpful introduction to what follows, a way to ease into the fact that Milonakis does what he likes and doesn’t really give a crap what you think either way.

He’s a comedian, so, of course, he enjoys getting an audience to react. But working for the crowd has never been what drove him as an entertainer. To be totally honest, he always saw all the wacky shit he was filming as just that.

“I never thought of it as a means to make money or get any kind of success, because that never happened on the Internet,” Milonakis said. “I just thought of it as a fun outlet, something that seemed cool at the time.”

That would sound like a line, if YouTube even existed in 2003. User-generated content had only begun to emerge. “The Super Bowl Is Gay” was one of the first viral videos. It was arguably the first viral video to land its creator a TV show.

“It was pioneering in that it was the first show ever born from the Internet,” said Daniel Kellison, a producer on “The Andy Milonakis Show” and Jimmy’s partner at Jackhole Industries (now Jackhole Productions).

"It's crazy, considering the fact that most people still think he’s a teenager," Jonathan added. "He’s like the grandfather of all these kid Youtube stars."

Once Jimmy found Milonakis, he secured releases for more of his videos and recruited him to do correspondence pieces on “Jimmy Kimmel Live!” Milonakis moved to Los Angeles to keep working for the show and Jimmy tried to add him to the roster as an announcer, but ABC balked.

“Andy was much too weird for their liking,” he said. “And the writers didn’t know what to make of him either.”

Half guilty for talking Milonakis out of Queens and half knowing his humor had the potential for something bigger, Jimmy tried to figure out a way to turn his proto-YouTube star’s intriguing weirdness into a show. He reached out to MTV, where he knew an executive named Tony DiSanto, and pitched him the idea.

Miloankis’ videos might appear simplistic, but, as Kellison put it, “It’s not easy to be that simplistically funny.”

“There’s something about Andy that’s so appealing,” said Rob Anderson, a co-producer on “The Andy Milonakis Show” (and Kellison’s half-brother). “It’s his free associative ability, his willingness to be genuinely strange in a way that most people can’t pull off.”

Understanding that deceptive brilliance, Jimmy approached DiSanto. “The idea for Andy's show was you didn’t know it would be imaginary or not,” Jimmy said. “You didn’t know if the show existed in what appeared to be a child’s imagination or if it was real.”

Given Jimmy’s blessing, MTV bought the show and gave Milonakis and his team a form of carte blanche that is rare for network television. (See: The pilot, which begins with Milonakis eating chicken fingers from a massive, chicken-head Pez dispenser.)

“It was such a wonderful confluence of events that led to this. Jimmy finding Andy, Andy finding MTV,” Anderson said. “You know, there’s an assurance, that Jimmy Kimmel is there and he’s going to take care of everything. That’s a lot of why it worked.”

Along with director Tom Stern, Jonathan Kimmel and Milonakis, Anderson set up the concept for the show. Their goal was to take Milonakis’ “lunacy” and smooth it out into a cohesive universe. Together, they set up a low-fi aesthetic with simplistic R. Crumb-style framing and an outerglow of the imaginary. Inspired by Paul Reubens’ Pee-wee, they created a world which allowed for a brand of absurdity that toed the line between seeming like reality and a child’s games of make-believe.

The key to that homemade aesthetic -- to the show in its entirety, really -- was renting an apartment on the Lower East Side. Stern and Anderson wanted to replicate Milonakis’ early video-making set up. He grew up in Queens, which wasn’t ideal for shooting purposes, so they scouted places that seemed like family homes in the city. The spot they eventually found on Grand Street was perfect, mostly for what lay outside.

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The cast was handpicked from the surrounding neighborhood. Recruiting sessions consisted of PAs hunting the streets with a camera to find the likes of Andy’s sidekick Ralphie. There was also the constant curveball searching for a new lineup of characters for each episode’s man-on-the-street bits -- an effort that would often require 10 hours of shooting for minutes of footage and even, according to Jonathan, incurred an attempted investigative piece by a New York paper accusing them of “harassing" residents.

As Milonakis and his crew remember it, though, the community loved them.

“It was like we were celebrities when we would go out on the street,” Stern said. “People were excited to see us.”

“We basically had a sketch show where most of the members of the troupe were over the age of 65,” Jonathan added, mentioning that he and the rest of the crew were like a surrogate family for the older woman who played Rivka.

Milonakis always had a passion for that wild card humor, and the Lower East Side proved the ideal environment for his antics. “The Andy Milonakis Show” featured celebrity guest stars ranging from Fergie to John Stamos, though Milonakis loved working with strangers the most.

“There’s something really awesome about that performance,” he said. “You can’t force it. With actors it’s awkward, it’s different than just some dude from the neighborhood.”

The randomness of the street segments was true to the tone of the show as a whole. (Though perhaps that doesn’t need to be said, since it had a reccuring character who was a piece of bologna.)

“The way it was structured was to not be structured as much as humanly possible,” Jonathan said.

For each episode, a team of writers would pitch hundreds of sketches built around the idea of Andy’s persona. From there, Jonathan, Anderson and Stern would consult MTV. The final product usually came from Milonakis working within that skeleton of approved skits, though most often he was given a loose framework, rather than dialogue, with most of the lines being improvised.

Even though the goal was to produce something that looked like videos made by a kid, the reality was this was a grown-man with a team of people behind him. It was all much harder than it looked. Writing and appearing in bits was exhausting. (OK, fine, that and, Milonakis admitted, maybe also all the partying he did at the end of the day.)

For a while Kellison actually had Milonakis sleep in the Lower East Side apartment to save money. Jonathan remembered banging on the door one morning for over an hour before he and the crew could get their leading man awake.

“Note that I’m laughing while I say this!” Jonathan clarified. “But, yeah, he’s a sleeper.”

When the show came to an end in its third season, after losing steam with the move to MTV 2 and a new set in LA, Milonakis was ready to be done.

“It was definitely bittersweet,” he said. “But after three years I was kind of beat down. I’ve had a lot of jobs in my life, I’ve worked at Blockbuster Video, I’ve worked at Kinko’s, I’ve worked at an air conditioning place, I worked at fucking General Electric. I’ve had so many jobs, pumping gas, busboy, and this is, hands down, [was] the hardest I have ever worked in my life.”

Milonakis at the 2006 MTV Movie Awards. (Photo: SGranitz via Getty Images)

It’s interesting to consider what kind of reactions “The Andy Milonakis Show” might have encountered if he didn’t look like a 14-year-old. Certainly, the food-smashing bits would have been a bit harder to digest. Less tiny old people would have interacted with him on the street.

“I think it’s really one of the great disguises,” Jimmy said, reflecting on Milonakis’ appearance. “Nature gave him the best possible comedy disguise and I think people respond differently because of that.”

The show’s tone hung on the notion that Milonakis was a child. His age wasn’t necessarily kept secret, but Jimmy found an air of mystery to be appealing. He convinced Milonakis not to do studio interviews to maintain a certain enigma within “The Andy Milonakis Show” universe.

The goal was to allow the mystery to perpetuate the idea that Milonakis was as young as he looked. Jonathan, Stern and Anderson committed to that concept by keeping things clean. They tossed in the occasional curse word, but never moved into the blue, preserving the innocence they had built.

“I think one year we even won an award in Christian Excellence or something like that,” Kellison snorted. “That wasn’t our intention, but it was very true to the show.” And much of that is what allowed MTV to give Milonakis and his team the okay on some of the zanier sketches.

“On a lot of other shows, you have a fight with the standards and practice people because you want to go dirtier or show more,” Anderson said. “In this situation those constraints were ours. It worked, because the point was to play into some ambiguity of the childlike nature of the whole thing.”

Milonakis with his hip-hop group Three Loco in 2013. (Photo: Tom Briglia via Getty Images) — Milonakis with his hip-hop group Three Loco in 2013. (Photo: Tom Briglia via Getty Images)

More than a decade after becoming a public figure, Milonakis takes a similar stance to talking about his hormone condition.

It’s an item of interest the Internet has dedicated entire message boards to solving. Each of Milonakis’ videos, new and old, are met with a constant stream of comments about his age. A Milonakis truther tweets approximately every 45 minutes.

“I don’t talk about that,” he said, firmly at first, then softening a bit. “It’s weird. It’s just another thing for people to talk about and I like keeping that low-key. Let them keep guessing, you know?”

Considering Milonakis' current visibility, he deals with a lot of nonsense on the Internet. He usually laughs it off or responds with a joke, but he's still human, and sometimes it gets to him.

"People can be really mean," he said. "Have you ever met someone who was a successful, happy person that sits and writes shitty things to people on YouTube? I know a lot of people say stuff like that just to deflect negativity, but that’s an honest question that I ask myself."

These days Milonakis is doing a lot of anything and everything. For a while, he had a music group called Three Loco. He made a video with Chief Keef. He did a travel video series. A cooking series. He was recently on "The Kroll Show." Now, he’s deciding what to focus his energy on next.

On some level, it may seem like he’s reverted to the lower echelons of the Internet legend-building he started. But being less famous doesn’t make him a failure.

We have this way of talking about celebrities, like all they want is to be the most famous they could possibly be. Like there are no other options. Milonakis is objectively less relevant now than he was circa 2006. That doesn’t change the magic of his chubby kid Cinderella story. Being plucked from his day job by one of the biggest names in late night and building a television show out of some silly videos he made for fun is amazing even though it’s since, sort of, come to an end.

Ten years after the show aired, the way everyone Milonakis worked with talks about him is reflective of his brilliance as something that endures.

“He’s just such an original voice,” said one writer, Aaron Blitzstein. “Andy is 100 percent Andy, and that doesn’t happen anymore with people in comedy.”

“It’s such a total pleasure to work with someone with Andy’s sensibility,” Anderson said. “He’s he’s such a wonderful, genuinely eccentric, interesting guy.”

Even Kellison, who came across a bit flippant (read: Hollywood-producer-y) on the phone, donned an air of respect before hanging up. “I’ll tell you one more thing,” he said, growing stern. “The secret to Andy, and to anyone who succeeded in our world, is that he’s supremely talented.”

There’s a lasting impact to Milonakis’ humor and the surrealist whimsy he dove head first into back in 2003. There are so many deliberately bizarre programs and comedians now. It’s the model upon which the entirety of Adult Swim is based. But in so many of those new shows, and with so many of those new performers, you can see the strings. There’s a clear strain in mounting to a level of absurdity that just comes naturally to Milonakis.

“A lot of comedians try not to give a fuck, but they really do,” he said. “I’m not trying to appeal to anyone. I just get a kick out of pushing my weirdness to the limits.”

It’s there throughout our phone call, a sense of humor in his tone that is wacky, silly, kind and innocent all at once. This piece started after I tweeted at him a few weeks ago. Before I spoke to the Kimmels and the rest of the crew, there was a 50-minute conversation which came after he wrote something about "fapping" to the "The View."

I replied, asking for an interview, thinking, "Wow, what the hell happened to Andy Milonakis?"

A few minutes into our conversation, I felt guilty for ever wondering, but the answer is this: he's still a sweet guy, living his life and doing weird shit with no more motivation than making himself laugh.

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