Shane Gillis and John McKeever didn't just stumble into a hit. They basically built a comedy fortress. When you look at the Gilly and Keeves cast, it’s easy to focus solely on Shane because, well, he’s everywhere right now. But the "cast" is really more of a revolving door of Philly-area legends, stand-up killers, and McKeever's weirdly talented friends. It’s a collective. Honestly, it’s closer to a garage band than a traditional TV show production. They started with zero budget, filming sketches in houses that probably hadn't been dusted since the nineties, and somehow created the most culturally relevant sketch comedy since Chappelle's Show.
If you’ve watched "ISIS Toy Drive" or "Uncle Daycare," you’ve seen the core DNA of this group. It’s not just about the lines. It’s about the specific, grimy energy of the people on screen.
The Anchors of the Gilly and Keeves Cast
Obviously, Shane Gillis is the face of the operation. He’s the "Gilly." After the whole SNL debacle, Shane didn't go away; he just went home to Pennsylvania and started making exactly what he wanted. His ability to play a "lovable moron" or a "menacingly confident idiot" is the engine. But John McKeever—the "Keeves"—is the secret sauce. While he spends most of his time behind the lens directing, his appearances in front of the camera are usually the highlight of any sketch. McKeever has this specific brand of high-strung, frantic energy that balances Shane’s slow, deliberate delivery.
Then you have the guys who are in almost everything.
Steve Gerben is the MVP. If you don't know Gerben, you haven't been paying attention. He’s the guy who looks like he’s perpetually having the worst day of his life, which makes him the perfect foil for Shane’s bullying characters. In "The Special Day," Gerben’s performance is nothing short of heroic. He’s a writer and comedian in his own right, often collaborating on the scripts, and his timing is pinpoint accurate. He isn't just a "sidekick." He’s a foundational pillar of the Gilly and Keeves cast.
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The Philly Comedy Pipeline
A lot of the people you see in the background or playing bit parts are actual stand-up comics from the Philadelphia and New York scenes. This isn't a cast of "actors" who went to Juilliard. These are people who spend their nights in windowless basements telling jokes to twelve people.
- Matt McCusker: The co-host of Matt and Shane's Secret Podcast. He doesn't show up in every single sketch, but when he does, it’s usually legendary. His natural chemistry with Shane is something you can't manufacture in a casting office.
- Tommy Pope: A Philly comedy powerhouse. He’s got that specific Delco/Philly vibe that makes the sketches feel authentic. He often plays the "straight man" who is slowly losing his mind.
- Chris O'Connor: Another frequent flyer. He’s often the guy trying to maintain some level of sanity while the world collapses around him.
- Brian Six: Also known as Beezer. He’s part of that tight-knit crew that brings a level of grit to the comedy.
These guys aren't just there to fill space. They understand the "vibe" of McKeever’s directing. There is a specific pacing to a Gilly and Keeves sketch—it’s fast, it’s visually dirty, and it relies heavily on reaction shots. If the cast didn't have that shared shorthand, the sketches would just be funny scripts. Instead, they feel like weirdly high-def home movies.
Why the Casting Works Better Than SNL
The problem with mainstream sketch shows is that they try to be everything to everyone. They hire a "diverse" cast of performers who have never met before and tell them to be funny together. Gilly and Keeves does the opposite. They hire their friends.
This creates a level of comfort that allows for genuine risk-taking. When Shane is playing a guy who thinks he’s in a movie while getting arrested, the other actors aren't just waiting for their turn to speak. They are reacting in a way that feels lived-in. You see it in sketches like "Sleepover." The chemistry between the kids (and the adults) feels like a real, albeit dysfunctional, family.
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The production value is surprisingly high, too. Despite the DIY feel, McKeever is a technical wizard. He knows how to make a suburban kitchen look like a cinematic set piece. But the set only works if the people in it belong there. You wouldn't put a polished Hollywood actor in a Gilly and Keeves sketch; they’d look like a sore thumb. You need someone who looks like they just finished a shift at a Wawa.
The Role of Guest Stars and New Faces
As the show grew, especially with the release of Gilly and Keeves: The Special, the cast expanded. We started seeing more recognizable faces from the broader comedy world.
Think about the "Dublin" sketch or the parodies of historical dramas. They’ve brought in guys like Foley and Kevin Ryan from the Are You Garbage? podcast. This isn't just "influencer casting." It’s about building a universe. By bringing in other comedians who share their sensibilities, they’ve created a sort of "Cinematic Universe" of degenerate comedy. It’s smart. It keeps the fans of the podcasts engaged while providing a platform for some of the best-underrated talent in the country.
Breaking Down the "Vibe" Actors
There’s a category of the Gilly and Keeves cast that I like to call "The Vibe Actors." These are people who might not even be "comedians" in the traditional sense, but they have a look or a presence that McKeever exploits perfectly.
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You’ll see older guys playing dads or neighbors who just have "the look." They have the authentic Northeast aesthetic—the tracksuits, the slightly weathered faces, the skeptical squint. This realism is what makes the absurdity of the dialogue work. If the world looks real, the crazy stuff Shane says is ten times funnier.
Key Standout Performances to Rewatch
- Steve Gerben in "The Special Day": I mentioned it before, but his commitment to the physical comedy and the sheer pathos of the character is insane.
- John McKeever in "Trump Speed Dating": While Shane does the heavy lifting with the impression, McKeever’s hosting energy is what grounds the sketch.
- Tommy Pope and Chris O'Connor in "Family Meeting": The tension they build is palpable. It feels like a real argument you’d overhear at a diner in South Philly.
The Production Behind the People
It’s worth noting that the cast also doubles as the crew. In the early days, and even now to an extent, everyone was pitching in. This "all hands on deck" mentality translates to the screen. There’s no ego. If Shane needs to be the butt of the joke, he is. If a guest star needs to take the lead, the regulars step back.
This lack of hierarchy is rare in entertainment. Usually, the "star" wants the most lines. In Gilly and Keeves, the "star" is often the one getting yelled at or looking the most ridiculous. That’s why the cast is so beloved; they’re a unit.
Actionable Insights for Fans and Creators
If you’re looking to dive deeper into the world of the Gilly and Keeves cast, or if you're a creator trying to emulate their success, here is the real-world takeaway:
- Follow the Podcasts: To truly understand the cast, you have to listen to Matt and Shane’s Secret Podcast, Stoner Dadz, and Dad Meat. That’s where the "lore" of the cast is built. You’ll hear them discuss the sketches months before they come out.
- Watch the Credits: Don't just skip them. Look at the names. Many of the people in these sketches are writing and producing their own content. Following the "Philly Tree" will lead you to some of the best comedy being made today.
- Study the Directing: If you’re a filmmaker, watch how McKeever uses his cast. He doesn't over-direct. He lets the natural awkwardness of the performers breathe. The "silence" in a Gilly and Keeves sketch is often funnier than the dialogue.
- Support Independent Comedy: The reason this cast exists is that they bypassed the traditional gatekeepers. They didn't wait for a network to say "yes." They used Patreon and YouTube to fund their own vision. Supporting their independent specials ensures we get more of this cast and less of the "sanitized" stuff on cable.
The Gilly and Keeves cast is a testament to what happens when talented people stop asking for permission and just start filming with their friends. It’s raw, it’s frequently offensive, and it’s consistently the funniest thing on the internet. Whether you’re there for Shane’s impressions or Gerben’s suffering, the ensemble is what makes the engine purr.