Early internet star turned celebrity Andy Milonakis revolutionized live streaming and virality, but he still has regrets

Andy Milonakis is 45 now but shows no signs of slowing down.
Since creating his own television show in 2003, he's been a rapper, actor, performer, and live streamer.
A pioneer of the internet age, Milonakis feels he gets "judged" for his appearance.
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Andy Milonakis has spent the past two months in the mountains on the island of Crete, Greece at his grandparent's house. Almost every day, he livestreams the gorgeous landscape to thousands of viewers on Twitch.

The 45-year-old television star, content creator, rapper, influencer, and comedian has managed to keep his career alive for nearly two decades after he went viral pre-YouTube. Listing his accomplishments sounds a bit like you created a career with a random generator: he achieved mainstream success on MTV with "The Andy Milonakis Show," voiced a microwave in a children's television show, started a rap group with actor Simon Rex, and pioneered real-world live-streaming on Twitch.

Insider spoke to Milonakis about his career, how he got his start live streaming on Twitch and what he hopes he can achieve in this next phase of his career.

Milonakis was the first viral star to get his own television show

Milonakis was born in 1976 in Katonah, New York with a congenital growth hormone deficiency that gives him the appearance and voice of an adolescent.

After high school he moved to Queens in the late 90s and dabbled in the world of comedy, taking improv and writing classes at the Upright Citizens Brigade theater while working in tech support at an accounting firm as a day job.

In the late 90s, he was an early participant in internet comedy with his "child actor" website, where he posted photos of himself "making really weird faces" and wrote with "really bad grammar that's misspelled on purpose to just make me seem totally out of my mind."

"Back then, nobody succeeded making comedy on the internet, it wasn't even a thing," Milonakis said.

Brian Lynch, the future screenwriter of "Minions" and "Hop" invited him to be a part of his website AngryNakedPat.com in "1999 or 2000" Milonakis recalls. By the early 2000s, before YouTube was founded, Milonakis had posted over 100 videos on the site. In 2003, he was debating giving up on the videos because they weren't getting many views] but he felt the sudden urge to purchase a plastic ukulele from a lady selling them from a shopping cart.

"My friends invited me to a Superbowl game and I just, I didn't really like sports. So I was like, I'm going to make a video about it," Milonakis recalls.

Filmed on a grainy webcam, Milonakis changed his life trajectory after he posted his breakout viral hit, "The Superbowl is Gay." The three-minute clip of Milonakis calling everything from DVDs to McDonald's "gay," outdated and somewhat offensive humor by today's standards, went viral at the time. Radio stations across the country contacted Milonakis for interviews.

One of those original viewers was Jimmy Kimmel, who had started hosting his Jimmy Kimmel Live show and found an affinity for the comedic actor. Over the next couple of years, Milonakis would make guest appearances on the talk show, with Kimmel saying in a 2005 Washington Post article that "his comedy is something that probably would have been around a long time ago if kids had access to video cameras and editing machines and the Internet."

Kimmel's endorsement led directly to MTV, according to Milonakis. An executive had been badgering Kimmel for a television show to pitch, which started as scrounged together clips from the web and Jimmy Kimmel Live. With the talk show host spearheading the pitching process, it led to a pilot, which was one of 20 vying for a spot to be made into a television show. Milonakis' show eventually won out.

The Andy Milonakis Show premiered on MTV in 2005 and ran for three seasons. The show was an absurdist, surrealist nightmare that used random people as actors. Man on the street segments where he plays up his childish persona are intertwined with celebrity appearances from early aught icons like Hillary Duff and Lil Jon.

The show was a massive success and turned Milonakis into a traditional celebrity. Over the next two decades he made appearances or lent his voice to shows like Adventure Time, The Kroll Show, and Crank Yankers. But ultimately the world of TV wouldn't be where he made his biggest and longest impact.

He appeared on Snoop Dogg's internet news show, hosted his own YouTube cooking show called "Andy's Hungry Voyage," and had a fairly successful rap career.

Milonakis' YouTube channel has half a million subscribers and has pulled in over 100 million views since it was created in 2006. "G L O G A N G," his 2015 music video featuring Chief Keef has over five million views and his group Three Loco with Riff Raff and actor Simon Rex has over 10 million views across their dozen or so videos from 2012.

Andy joined Twitch and pioneered the world of IRL streaming

In 2016, Milonakis started to gain renewed attention with his Twitch streams. After initially streaming PS4 and PC games, Milonakis turned to "Pokemon Go," the highly successful mobile game where users capture Pokemon by exploring the real world.

On that first stream, Milonakis recalls, he went from "a couple hundred viewers to 1,200." Over the next year, he'd gain 200,000 followers, who watched him order tacos, walk around Los Angeles, and hang out with other streamers.

Milonakis quickly fell into a crew of influencers who streamed on Twitch's "IRL" section, who frequently did outrageous stunts for clicks.

"I would walk up and down Hollywood Boulevard with like the craziest people, the weirdest drunks," Milonakis said. "I would be drunk, like making out with chicks and like just doing stupid sh--."

Several members of Milonakis' crew found themselves in hot water. One was banned from Twitch after police were called on him without cause while he was on an airplane. Another was arrested live on stream in 2019.

"At the time, it seemed fine I guess, but looking back it sounds like hell," Milonakis said. "And then once I wizened up, I was like, 'Oh, man. Why do I just have to be here? I can be traveling.'"

In June of 2017, Milonakis met up with streamer EXBC in South Korea and fell in love with the idea of IRL streaming while traveling, which led him to Japan and Greece. Until the pandemic hit in 2020, Milonakis was traveling as much as he could, streaming to thousands in the process.

"I really do love the ability to be my own boss and fly all over the world and stream it live," Milonakis said.

Milonakis says he regrets a lot

Milonakis has been making videos online for 20 years and regrets a large amount of time where he said he worked at "10% capacity," he said.

"I don't want to live my life where I just constantly am a workaholic and I don't enjoy life, but I feel like I could've given it a lot more," Milonakis said. "I'm not beating myself up over it, but it could have been pretty dope to work harder during those years."

Milonakis has no plans of slowing down. His idol is Anthony Bourdain and hopes to one day create a show with his unique brand of humor, spitballing the idea of going to the best "sushi place in Japan and taking the food very seriously" but then dress up "as a ball of rice doing a rap video."

"I think a lot of people write me off as that stupid, weird kid, which I am in a lot of ways, but I feel like I have more to offer," Milonakis said. "I feel like when people kind of judge me and look at me in a weird way, I feel like I have my head on my shoulders and I feel like I'm very socially aware. I know how to talk to people and know how to treat people. And when I do really weird, crazy shit, I feel like people don't expect that of me."

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