You probably know the face. It’s that stoic, slightly concerned look of a man holding a puke bucket for a C-list celebrity who’s currently trying to explain the Boston Tea Party while three sheets to the wind. That’s Derek Waters. Most people basically pin him as the "Drunk History guy" and call it a day. Honestly, though? If you look at the full run of derek waters movies and tv shows, you realize he’s been the secret sauce in alt-comedy for over twenty years.
He didn't just stumble into a Comedy Central hit. It was a grind.
Baltimore born and bred, Waters moved to LA and started doing the rounds in the early 2000s. He wasn't some industry plant. He worked at Tower Video. He stocked shelves and watched indie movies he’d never heard of. That vibe—that weird, specific, "I know too much about obscure cinema" energy—defines everything he’s done since.
The Mythic Quest Connection and 2025’s Side Quest
If you’ve been keeping up with Apple TV+, you’ve seen him as Phil in Mythic Quest. Phil is... well, Phil is a lot. He’s the office punchline. He’s the guy who seems like he might dissolve into a puddle of anxiety if someone looks at him too hard. For years, fans thought Phil was just a background gag.
Then came 2025.
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The spinoff Side Quest actually gave him room to breathe. Waters recently talked about how he thought his character was basically dead in the water, but the showrunners brought him back to explore what he calls a "tormented man." It’s a mix of that signature deadpan humor and some surprisingly heavy drama about work-life balance and anxiety. It’s arguably some of his best acting work because it moves past the caricature.
Why Drunk History Still Matters (And Why It Vanished)
We have to talk about the elephant in the room. Drunk History was massive. It started as a web series on Funny Or Die back in 2007 after Jake Johnson (yep, Nick Miller from New Girl) told Waters a story about Otis Redding that was so incoherent Waters envisioned a reenactment.
The show ran for six seasons on Comedy Central. It won Emmys. It featured everyone from Lin-Manuel Miranda to Winona Ryder. Then, in 2020, it just... stopped.
The Cancellation Confusion
Comedy Central was shifting toward adult animation. They wanted more South Park and less live-action production. Even though Season 7 was technically greenlit and partially prepped, the pandemic and the network’s pivot killed it. Waters has been pretty open about it being a bummer. He still has a first-look deal with Comedy Central through his production company, Be Nice or Leave Productions, but the legal red tape of "owning" the Drunk History name makes a revival tricky.
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He’s mentioned in recent interviews that he’d love to do specials. He even joked about filming them in his backyard again, just like the old days. But for now, the show exists in that weird streaming limbo where we all just hope for a surprise drop on Paramount+.
The "Derek & Simon" Era
Before the booze-fueled history lessons, there was Derek & Simon. This was a partnership with Simon Helberg. You know, Howard Wolowitz from The Big Bang Theory.
They were a sketch duo that caught the eye of Bob Odenkirk. Think about that. The guy who created Mr. Show and became Saul Goodman saw something in them. They made web shorts like The Pity Card (which featured Zach Galifianakis) and A Bee and a Cigarette. It was awkward, cringe-heavy comedy before that was even a mainstream thing. If you want to understand the DNA of derek waters movies and tv shows, you have to go back to these shorts. They are the blueprint.
Film Credits You Probably Missed
Waters pops up in movies constantly, usually as the weirdest guy in the room.
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- Hall Pass (2011): He plays Brent. It’s a Farrelly Brothers movie, so it’s exactly as chaotic as you’d expect.
- The Brothers Solomon (2007): A cult classic. If you haven't seen it, find it. He’s in there with Will Arnett and Will Forte.
- For Your Consideration (2006): Christopher Guest movies are the gold standard for improv-adjacent comedy, and Waters landing a spot here early in his career says a lot about his reputation among "comedian's comedians."
- Girlfriend’s Day (2017): He reunited with Bob Odenkirk for this Netflix noir-comedy about greeting card writers.
He’s also done a ton of voice work. He was in American Dad! as Gorney and played a self-centered weasel named Dipster in a 2012 web series called Weasel Town. He has this ability to play "uncomfortably earnest" better than almost anyone else in Hollywood.
What’s He Doing Now?
Beyond the 2025 release of Side Quest, Waters has been leaning into directing. He directed a music video for Ben Folds in 2023 for the song "Exhausting Lover." It involves a Motel 6, a Hot Wheels track, and dancers in animal costumes. It’s very Derek Waters.
He’s also been working with RepresentUs, a nonpartisan nonprofit. He’s using his platform for more than just laughs, focusing on making voting easier and fighting corruption. It’s a pivot, sure, but it fits his interest in how the "system" (historical or political) actually functions.
Actionable Ways to Catch Up on His Work
If you’re looking to dive into the Waters filmography, don’t just stick to the hits.
- Watch "Derek & Simon: The Show": It’s harder to find now, but some clips are still on YouTube. It’s essential viewing to see his chemistry with Simon Helberg.
- Binge the "City" episodes of Drunk History: The show was best when it focused on specific locations like Charleston or Detroit rather than just "Famous People."
- Check out Side Quest on Apple TV+: Specifically for his performance as Phil. It’s the most "human" he’s been allowed to be on screen.
- Follow Be Nice or Leave Productions: This is where his new development deals will eventually land.
Waters is one of those guys who has stayed relevant by being a great collaborator. He’s not trying to be the loudest person in the room; he’s the one making sure the loudest person is actually funny. Whether Drunk History ever officially returns or not, his fingerprints are all over the last two decades of smart, weird television.
Keep an eye on his guest spots too—he has a habit of showing up in shows like New Girl, The League, and It's Always Sunny in Philadelphia just long enough to steal a scene and disappear. That’s the Derek Waters brand: show up, be weird, make it memorable, and move on to the next project.