Oh, Dennis Reynolds, the resident sociopath of It’s Always Sunny in Philadelphia. Thanks to Glenn Howerton’s mastery of comedic timing, there’s an argument that Dennis is the show’s funniest character. That said, a similarly strong argument could be made for Rob McElhenney’s Mac, Danny DeVito’s Frank, Kaitlin Olson’s “Sweet” Dee, and Charlie Day’s Charlie. In other words, it’s a show where all five scheming, foul-mouthed protagonists are pretty much tied for first. And, given how the show has been running for 20 years now, each of those characters have received episodes that expand their respective personalities in noteworthy ways. And it’s not always in an episode where they’re fronting the A-plot.
What follows are some of those episodes for Dennis. “Some” because Season 4’s “Dennis Reynolds: An Erotic Life” and the “Mac and Charlie Die” two-parter didn’t make the cut, nor did Season 6’s “Mac Fights Gay Marriage” and “Dennis Gets Divorced.” Yet they too are incredibly important. “An Erotic Life” shows us just how much of a sex symbol Dennis deems himself to be. Meanwhile, the “Mac and Charlie Die” duology has him explain what a glory hole is, and it’s glorious. Then there’s that Season 6 duology, which introduces none other than Maureen Ponderosa…the woman he marries, divorces, pays for her transition into a cat, and, ultimately, “maybe” murders.
1) “The Gang Exploits a Miracle” (Season 2, Episode 7)
Dennis’ extreme, unhealthy vanity was a presence in the character even early on. His cohorts seem to acknowledge this as well. For instance, he, Mac, and Charlie just kind of accept and agree upon the fact that their dynamic is “The Looks, the Brains, and the Wildcard.”
But this is something Dennis takes too far, and too much to heart, the very moment the concept of his fading looks pops up. For instance, in Season 7’s “How Mac Got Fat,” which sees him get a chemical peel and die his hair black. Then there’s the Season 2 masterpiece “The Gang Exploits a Miracle,” which sees both the A and B-plot firing on all cylinders. As for the B-plot, it really just comes down to Dee telling Dennis his face looks fat, at which point he begins to starve himself (and, at one point, equate his vain attempt to decrease the size of his already slender face to “Jesus and Moses out in the desert”).
2) “The Gang Finds A Dumpster Baby” (Season 3, Episode 1)
Dennis’ vengeful nature is the ultimate quality of his that has grown as the series has progressed. If he’s wronged, you better believe he’ll come back with a quickly yet thoroughly thought-out plan carried out via manipulation and fueled by vindictiveness. He comes back with both barrels, in metaphorical terms. It’s just, later in the show, you wonder if that metaphorical nature might be swapped out for a literal one.
The best early days example of this is in “The Gang Finds a Dumpster Baby,” where a hippy turns him away when he tries to become an environmentalist. On one hand, he wants to do this because he just watched An Inconvenient Truth and wants to combat the “sad, throwaway culture” we’re living in. On the other hand, you know he’s just in it to inflate his ego. Either way, he gets rejected, which sets him down a course of sleeping with the condescending hippy’s girlfriend after planting in his head the idea of tying himself to a tree. Then, after sleeping with the girlfriend and untying the man, he waves on a bulldozer to tear down the tree.
3) “America’s Next Top Paddy’s Billboard Model Contest” (Season 4, Episode 3)
Dennis’ neediness is pretty well tied to his vanity. His opinion of himself always comes in first place, but he also needs that inflated view of self positively reinforced by a third party, even if he has absolutely no respect for that third party.
This is especially true if that third party he has something he wants, usually something that will help further inflate his already bloated vanity. Like a billboard. Then again, that bloated view of self can mislead Dennis, like when he’s in a contest to be on the aforementioned billboard and his competitors are actual stallions. To watch him play a losing man’s game of that type is compelling stuff.
4) “Mac and Dennis Break Up” (Season 5, Episode 9)
Dennis likes to think he’s independent. He likes to think he genuinely doesn’t need anyone, especially Mac. But he’s wrong and Season 5’s “Mac and Dennis Breaks Up” proves it.
When Dee insinuates that they would be lost without one another, Mac and Dennis decide to go their separate ways for a short time. For Mac, this makes him needier than ever. The same thing happens with Dennis, but in his case it’s arguably even stronger and less expected. He just wants to watch Transporter 2, but Dee has her attention locked on getting a cat out of her wall. So, still in her apartment, he gets Charlie over to watch the movie with him. But, given how the situation involves cats, Charlie’s attention also moves to the wall. Dennis pathetically sits in the background asking if they’re ready to watch the movie. That is, until he swallows an apple seed and goes to the toilet to emit the most hilarious vomiting sound in television history.
5) “The D.E.N.N.I.S. System” (Season 5, Episode 10)
It’s always been hinted at that Dennis has the confidence to do well with women. But it wasn’t until Season 5 that he, quite excitedly, explained just how he does so well.
As it turns out, he just flat-out plays horrible mind games. The entirety of his system in “The D.E.N.N.I.S. System” is so on-brand for him that it’s naturally one of his best episodes. But it’s also just a well-constructed 20 or so minutes of television. There’s also charm in knowing that the actress playing the latest target of his system is his real-life wife.
[RELATED: 10 Best It’s Always Sunny in Philadelphia Episodes]
6) “The Gang Buys a Boat” (Season 6, Episode 3)
“The Gang Buys a Boat” is a great episode for the entirety of the gang, but mostly for Dennis, and this is all because of one scene.
Dennis’ monologue about “the implication” is both his most iconic and a notable turning point. This is the first time we truly see Dennis as a full-on predator (even more so than in “The D.E.N.N.I.S. System”). He even has a name for his process of making women feel trapped. The fact that Howerton sells it all in a way that’s funny, even through a dead-eyed stare, is seemingly something only he can do.
7) “The Storm of the Century” (Season 7, Episode 6)
Charlie has the Waitress, Dennis has Jackie Denardo. Or, in Dennis’ words, “Charlie, I might be in love with this woman…not for the right reasons, mind you.”
He’s referring to the newscaster’s breasts. Their size is really the only thing he knows about her. And their size is enough to make the ultra-confident man quiver and studder when he finally comes face-to-face with her. Denardo actually came back twice after “The Storm of the Century,” once in Dennis’ daydream in “The Gang Saves the Day,” which has every member of the gang hallucinate their ultimate dream, and once in Season 14’s “Paddy’s Has a Jumper,” in which she only shares screentime with Frank (who is equally enamored with her).
8) “The Gang Gets Quarantined” (Season 9, Episode 7)
“The Gang Gets Quarantined” is really a great episode for all five characters. For Frank because it focuses on his descent into paranoid insanity revolving around his newfound fear of hair. For the others, because they’re locked in Paddy’s bathroom experiencing alcohol withdrawal.
The first one to experience withdrawal is Dennis, who has been obsessing over the gang getting their harmonizing right so they can open for Boyz II Men. Meaning, he’s been refraining from drinking to spare his throat. All of the gang ends up vomiting uncontrollably and getting the shakes, but Dennis ends up looking like an absolute ghost. To prove to Mac and Dee that he’s feeling fine, he asks them if a sick man could belt out a drawn out, high-pitched note (by belting out that drawn out, high-pitched note), to which Mac replies, “Yeah, dude.”
9) “The Gang Misses the Boat” (Season 10, Episode 6)
“The Gang Misses the Boat” is an interesting episode and, given how it has Charlie and Dee have sex, an important one. But it’s also important for Dennis as it’s arguably the first time we really see him lose control over his temper. His Range Rover has been submerged in water and, instead of getting it out, he attempts to sell it. Finally, he meets an interested buyer who isn’t put off by it being submerged. But then the prospective buyer lets slip that he’s going to be purchasing it for his daughter, as a “Starter car.” To that, Dennis lets loose with one of his most iconic rants to date.
“I have contained my rage for as long as possible, but I shall unleash my fury upon you like the crashing of a thousand waves! Begone, vile man! Begone from me! A starter car? This car is a finisher car! A transporter of gods! The golden god! I am untethered, and my rage knows no bounds!”
10) “Mac & Dennis Move to the Suburbs” (Season 11, Episode 5)
“Mac & Dennis Move to the Suburbs” has screentime for Charlie, Dee, and Frank, but this is really the two title characters’ episode all the way through. As the years have gone on, Mac (especially after officially coming out of the closet) has grown increasingly obsessed with Dennis and, in turn, Dennis has become increasingly dismissive of Mac.
This episode essentially locks them in a location that’s far away from their big city comfort zone and it works like a charm. Both characters go insane in their own ways, with Mac chopping up a dog (which he names Dennis) and feeding it to Dennis in a bowl of mac and cheese and Dennis, well, fantasizing about stripping naked and screaming at a neighbor.
It’s Always Sunny in Philadelphia returns for its Season 17 debut (the second part of the Abbott Elementary crossover) on July 9th.
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