If you were scrolling through Twitter or lurking on rap forums back in early 2015, you probably remember the collective "what the hell?" that echoed across the internet. Out of nowhere, Chief Keef—the king of Chicago drill and a man who arguably invented modern mumble rap—started posting photos with Andy Milonakis. Yes, the guy from the MTV show with the bowl cut and the pancakes.
People thought it was a joke. Maybe a one-off skit? But then the music started dropping.
The Andy Milonakis Chief Keef era wasn't just a brief crossover; it was a legitimate creative partnership that resulted in a handful of tracks, a classic mixtape appearance, and some of the trippiest music videos of the decade. This wasn't two celebrities shaking hands for a PR stunt. They were actually hanging out, smoking blunts in the studio, and making music that felt like it was beamed in from a different dimension.
How the Hell Did This Happen?
Honestly, the way they met is peak 2010s internet. There was no corporate middleman or label-mandated collaboration. It started because Chief Keef actually liked Andy’s humor and his previous rap attempts.
Milonakis had been in the rap periphery for years, specifically with Three Loco (his group with Riff Raff and Dirt Nasty). Keef hit up Andy on Twitter, but nothing really came of it at first. Then, in a move only Sosa could pull off, he noticed Andy had unfollowed everyone on Vine. Keef messaged him saying something like, "I know you aren't following anyone, so you should only follow me."
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Eventually, Keef invited him to his house in California. Andy took an Uber—a matte black SUV, naturally—and showed up with some lean. They didn't even plan to record. They were just listening to beats in Keef’s guest house when someone realized they needed a microphone. They ended up at a studio in Burbank that same night, and Andy wrote six songs in one session because Keef kept texting him from the booth, asking for verses.
The Music That Defined the Era
When Andy Milonakis and Chief Keef finally released their collaborations, the production was handled mostly by DP Beats (DPGGP). The sound was murky, melodic, and heavily Auto-Tuned. It fit perfectly into the Almighty So and Sorry 4 the Weight era of Keef’s career.
"G L O G A N G"
This is the big one. If you haven't seen the video, it’s basically Keef and Andy flying through space in a Rolls-Royce. There are aliens. Andy is surfing on the rings of Saturn. It’s low-budget green screen gold. But the song actually goes hard. Andy's line, "Got more pints than a blood drive / pouring fours this is mud life," became an instant meme but also proved he could actually flow over a drill beat.
"My House"
This track was the follow-up, and the video was the polar opposite of the space odyssey. It was just Keef and Andy in the studio, surrounded by so much smoke you could barely see the camera lens. It felt grounded and real, showing that the friendship was more than just a gimmick for a music video.
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"Hot Shit"
Appearing on the Sorry 4 the Weight mixtape in 2015, this track cemented Andy as an honorary member of the Glo Gang. At a time when Keef was distancing himself from major labels and doing his own thing, having a 39-year-old comedian (at the time) as his primary feature was the ultimate "I don't care" move.
Why the Partnership Actually Worked
It’s easy to dismiss this as irony, but there was a weird synergy between them. Chief Keef has always been an outsider. Even when he was the biggest rapper in the world, he didn't play by the industry's rules. He stayed in his house, played video games, and recorded music whenever he felt like it.
Andy Milonakis is the same way. He’s an internet pioneer who became famous by doing weird stuff in his bedroom. They both share a sense of humor that is deeply rooted in "randomness" and internet culture.
Critics at the time were confused. VICE called their collaboration an "out-of-nowhere masterpiece." Some fans hated it, thinking Andy was mocking the genre. But if you look at the studio footage, Keef is genuinely hyped. He wasn't laughing at Andy; he was laughing with him.
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The Impact on Glo Gang
The inclusion of Andy into the Glo Gang circle helped bridge the gap between "street rap" and "internet rap." It paved the way for the "SoundCloud Rap" explosion that would happen a year or two later. Suddenly, you didn't have to be a tough guy from the South Side to be in the room; you just had to be interesting.
Andy even got a shoutout (and a feature) from Gucci Mane around this time. Fredo Santana, Keef’s cousin and one of the most feared figures in the drill scene, was also a fan of the collaboration. If Fredo gave you the pass, you were officially "Glo."
What Happened to the Duo?
Like most things in the fast-moving world of hip-hop, the constant collaborations eventually slowed down. Andy moved more into the world of Twitch streaming, becoming one of the biggest "IRL" streamers on the platform. Keef continued his evolution, releasing dozens of projects and becoming a legend to the new generation of rappers.
They haven't had a major falling out; life just moved in different directions. But the Andy Milonakis Chief Keef era remains a specific, neon-colored timestamp in history. It represents a time when the internet felt smaller and more unpredictable.
Practical Takeaways for Fans
If you're looking to dive back into this specific era of internet history, here is how to find the best of it:
- Watch the "G L O G A N G" Music Video: It is the essential artifact of this partnership. Search for the version directed by Sean Barrett.
- Listen to "Sorry 4 the Weight": This mixtape is peak 2015 Sosa. "Hot Shit" is the track to look for.
- Find the "My House" Studio Footage: There are behind-the-scenes clips on YouTube that show the genuine vibe of their recording sessions.
- Check out "Runnin": This is a lesser-known track produced by Almighty DP that shows their melodic chemistry.
The collaboration proved that genre and background don't matter as much as a shared "weirdo" energy. It’s a reminder that the best parts of the internet are often the ones that make the least sense on paper.