5 Best Glenn Howerton Moments In It’s Always Sunny In Philadelphia

The long-running FX sitcom “It’s Always Sunny in Philadelphia” is a phenomenal showcase for its central cast of characters, letting them go wilder with their comedy than many other shows would dare. 

Over the show’s 17 seasons, audiences have seen a lot of mayhem from the self-titled “gang,” comprised of twins Dee (Kaitlin Olson) and Dennis Reynolds (Glenn Howerton), their alleged father Frank Reynolds (Danny DeVito), the semi-illiterate janitor Charlie (Charlie Day), and Dennis’ oft-closeted Catholic roommate Mac (Rob Mac). Charlie faked having cancer. Dee had a baby. The gang went to Ireland and threw a body off a cliff. They even did community service at an elementary school in a pair of crossover episodes with “Abbott Elementary,” proving that their comedic range has almost no bounds.

While his co-stars are fairly well-situated in the world of comedy, Howerton is a classically trained actor from The Juilliard School, and his dramatic chops are wildly impressive as well. The actor almost left “It’s Always Sunny” more than once to pursue his other career interests, but thankfully, he hasn’t, because Dennis is an all-time great television character. Howerton brings an impressive amount of depth and nuance to a man that could easily be played like a cartoon, and he’s had some truly killer moments on the show over the years. Let’s take a look at the five best, though there are certainly loads more. 

In the Season 8 episode “Charlie Rules the World,” Dennis becomes frustrated with the gang when they become obsessed with a multiplayer online game that allows them to live out their digital fantasies. In an attempt to gain control over the gang once more, he looks inward, taking a little trip inside a sensory deprivation tank and having a conversation with a version of himself he calls “British Dennis.” Howerton’s fake British accent is passable to American ears and pretty excellent compared to the one Dennis attempts to do once he sees the gang again in the waking world, but just seeing the way Howerton interacts with only himself onscreen is a real treat. 

Not only does Dennis come up with a plan to usurp Charlie’s kingdom, but he declares that he is a god, and it’s one of the first times we really get a glimpse of Dennis’ true megalomania. It’s an idea they would eventually return to for the Season 16 finale, “Dennis Takes a Mental Health Day,” which is another great display of Howerton playing Dennis as a terrifying narcissist. Dennis is a funny character, but a lot of that humor is rooted in the fact that it’s a good thing he’s not a real person, because he’s an absolute monster who has done terrible, horrible things.

At the end of Season 12, it looked like Howerton was possibly going to walk away, with Dennis going off to take care of the family he started on a trip to North Dakota. Thankfully, he came back and has been in almost every episode of the series since, giving fans line deliveries like no one else on television. While the scripts on “It’s Always Sunny” are more loose guidelines than hard rules for which words the cast uses, Howerton is almost always guaranteed to give a spin on the inflection, and the greatest of all is in the Season 14 episode “The Gang Chokes.” 

In it, Dennis becomes concerned about his health and safety surrounded by the rest of the gang, and he decides to go to bed early and get some rest. When his twin sister Dee teases him by calling him old, he replies with “we’re the same age,” except it’s really more like “wE’re thE SAme aGE” because his voice trills throughout the entire phrase. There are dozens of lines that Howerton delivered with just a little extra sauce, from his “not too hard, not too soft” speech in “The Gang Gets Quarantined” through his squealing of “this does not represent me!” on “The Gang Goes on Family Fight,” but his little retort to Dee in “The Gang Chokes” is simply the work of a master of voice control.

Usually Dennis has more puffed-up self-confidence than any human being rationally should, but on some rare occasions, he’s thrown off his game, and it’s always hilarious. Usually his narcissistic shell being cracked results in a full-blown meltdown of some kind, but it’s the smaller losses that are sometimes even funnier. In the Season 13 episode “The Gang Gets New Wheels,” Dennis loses his confidence because he doesn’t have his Range Rover any longer and has started driving a hybrid sedan. After being mistaken for a rideshare, he ends up going to a fantasy football party, where he tries to hit on the only woman there and fails spectacularly.

Howerton has played some sad sacks before, like disgraced Harvard professor Jack Griffin on the NBC sitcom “A.P. Bio,” but he is so overwhelmingly awkward as this swagless Dennis that it feels like you’re almost watching another actor entirely. He’s completely different in both his vocal performance and his physical presentation, and it’s impressive to see. 

Olson usually carries the heaviest load of cringe humor on “It’s Always Sunny,” but with this episode, Howerton showed that he could more than hold his own with his fictional twin. While he was also brought fantastically low in the Season 14 episode “Dee Day,” it’s no longer streaming on most services due to several characters doing racist caricatures, and the goofy awkwardness in “The Gang Gets New Wheels” is much more earnest. 

There are a couple of great meme-worthy Dennis moments that the series returns to in order to remind us that he is an absolute creep, but in the Season 7 episode “The Gang Buys a Boat,” he really takes it up a notch in a way that shaped the character moving forward. 

While he and Mac are buying boat supplies for their new “P. Diddy shrimping vessel” — a joke that hits a bit differently, post-Diddy sexual assault allegations — Dennis explains to Mac that he wants to take women out on the boat because of “the implication.” When asked what “the implication” means, Dennis is adamant that the women are in no real danger, but it’s the idea of danger that might make them sleep with him. It’s absolutely awful behavior, though it definitely falls in line with how Dennis treats women otherwise. This is a man who once tried to describe love as a woman’s head in a freezer, after all. 

While the joke behind “the implication” is really dark, it’s the way Howerton plays Dennis’ frustration with Mac over the whole thing that’s really funny. Mac being mildly horrified and Dennis being convinced he’s just “not getting it” is the real heart of the gag, along with Dennis’ cold, dead stare. By the time the implication comes back to bite Dennis in “The Gang Goes to Hell” when he tries it with a young woman on a cruise ship a few seasons later, it’s already the stuff of “It’s Always Sunny” legend. 

One of the best episodes of “It’s Always Sunny in Philadelphia” follows just Howerton and Mac (who changed his name from Rob McElhenney in 2025) as their characters move away from the rest of the gang and try to live in domestic bliss. In Season 11’s “Mac & Dennis Move to the Suburbs,” there are honestly a ton of great Howerton moments because he gets the chance to be at his most fully unhinged. As Mac and Dennis start driving one another mad and their goofy little McMansion instead becomes a house of horrors, Dennis finally snaps and goes off on his neighbor Wally (Steve Witting) after a bad day in traffic.

“Have you ever been in a storm, Wally?” he asks while he strips naked and strides across the lawn. The whole sequence is phenomenal, and when a fully nude Dennis screams demonically in Wally’s face, for us only to discover that the entire thing happened exclusively in Dennis’s imagination? That’s the kind of Dennis freakout that Howerton has made into a real work of comedic (and dramatic) art.