If you spend a decent amount of time on the Internet, you’ve likely heard of or seen Andy Milonakis on some corner of the Internet. Best known for The Andy Milonakis Show, he is a rapper, comedian, actor, and Internet personality.
For those who follow Andy Milonakis’ Internet existence, you may also know that the comedian is an avid poker player. Currently, Milonakis spends his time streaming on the platform Twitch and rapping under numerous pseudonyms — one of them fictional. Considering his highly varied skill set and interests, Milonakis certainly isn’t the first rapper known for his poker ventures.
In 2016, Soulja Boy inked a $400 million deal with World Poker Fund Holdings for a five-year-long endorsement. Fresh off his success producing and writing his own records since debuting in 2007, the online gaming provider praised Soulja Boy’s impact and influence on social media. The endorsement deal saw the rapper joining WPFH’s newly launched “celebrity-owned social gaming site” at the time.
Of course, Andy Milonakis’ trajectory takes on a different form when it comes to blending his love for comedy, poker, and rap music. In this post, we’ll take a look at how the comedian-rapper has balanced his multiple interests throughout his career and on the Internet:
Comedy
Arguably what launched Milonakis’ oddball career is his penchant for comedy. The Andy Milonakis Show, which aired on MTV and MTV2 from 2005 to 2007, is a sketch comedy series featuring Milonakis and a supporting cast of his actual neighbors and people from the Lower East Side, Manhattan neighborhood. The sketches border on absurdist and silly humor. The show had guest stars like John Stamos, Snoop Dogg, Jimmy Kimmel, and Hilary Duff throughout its three-season run.
Milonakis’ television work also includes voicing Neptr on the fantasy animated series Adventure Time and as the show’s announcer for Jimmy Kimmel Live! from 2003 to 2004. Afterward, Milonakis took his comedic talents to the Internet, where he streams a variety of content on Twitch, including IRL streams in locations like Greece, Japan, and South Korea. During these IRL streams, fans often come up to the comedian, at times to do pranks such as acting like an NPC game character in the background.
On the Internet, Milonakis’ comedy work extends beyond video content on Twitch and YouTube. The comedian is active on social media platforms like X (formerly Twitter) and shortform video platform TikTok, on which he refers to himself as a “silly boy rapper” who “had a comedy show on MTV”. Milonakis also implements his absurdist humor in the immersive Grand Theft Auto Online roleplay server, NoPixel — but more on that later.
Poker
Aside from spreading his comedic talents on the Internet, Milonakis also uses his Twitch platform — where he currently has over 640,000 followers — to share his passion for poker and casino gaming. In 2020, the comedian-rapper signed a one-year contract with online poker provider ACR Poker (formerly Americas Cardroom) to stream online poker games on his Twitch channel.
Milonakis’ interest in poker also led him to join ACR Poker for an online celebrity poker game for coronavirus relief in 2020, where he landed in the top three players, besting ACR CEO Phil Nagy on the way to the top. The comedian uploaded the video of his time “Knocking out Celebrities” in the poker tourney onto his YouTube channel, in which he shared poker tables with actors Jason Bateman, Sarah Silverman, and Jon Hamm. After a lucky hand, Milonakis also joked he was “gonna get fired” for having “just knocked out the CEO of Americas Cardroom.”
Set up as a stay-at-home poker tournament, the All In for America charity tournament took place online and was hosted by professional poker commentators Justin Kelly and Michael Loncar. Poker pro Ebony Kenney eventually won, but other names in attendance included superstars like Matt Damon, Ben Affleck, and Tobey Maguire, as well as Breaking Bad actor Bryan Cranston, who came in fifth place.
Rap
Finally, if you think you’re not familiar with Andy Milonakis as a rapper, it’s probably because he raps under a dozen different personas and rapper names. In 2010, Milonakis released his EP, “Gazpacho,” featuring seven tracks with a picture of a real-life bowl of gazpacho as the album cover. No doubt, Milonakis’ rap career is as much a mix of his love for comedy and absurdist humor as his work as an Internet personality.
Aside from his work as a solo artist, Milonakis was also in the comedy hip-hop group ¡Three Loco! with fellow rappers Simon Rex and Riff Raff. Simon Rex, like Milonakis, has a vast background in comedy, having starred in three of the horror parody Scary Movie films. ¡Three Loco!’s official release is the group’s debut EP under the group’s name, but the trio has also worked with producer and rapper Dame Grease on a song called “Off With Your Head” while he was mastering DMX’s “Undisputed” album. Dame Grease also went on to work with Riff Raff on other solo releases, including his “Hologram Panda” album.
While ¡Three Loco! was officially disbanded in 2014, Milonakis hasn’t stopped his rap music endeavors. As previously mentioned, the comedian-rapper is also active on GTA Online’s immersive roleplay server NoPixel. On the server, Milonakis plays Lollypop, or Ed Laurie, who is a “rapper proficient in freestyle raps.” The fictional character is recognized as co-owner and artist of the fictional Wu Chang Records and boasts a fictional criminal record consisting of jaywalking, reckless endangerment, and assault and battery — more than normal activities on any GTA Online server. On his YouTube channel, Milonakis has uploaded a few of his raps as Lollypop, all of which openly references fictional GTA Online and NoPixel elements.
Even if you aren’t wholly familiar with Andy Milonakis and his strange career, there’s no denying that very few rappers have had as prolific and flexible a career as the comedian-rapper. Paired with his seemingly random ability to dominate poker tournaments, Andy Milonakis is certainly a one-of-a-kind artist among his peers.