It’s Always Sunny in Philadelphia is about as dark as comedy gets. Following the misadventures of “The Gang”—Dennis (Glenn Howerton), Dee (Kaitlin Olson), Mac (Rob McElhenney), Charlie (Charlie Day), and Frank (Danny Devito)—is sometimes cringeworthy, often disturbing, and always hilarious. The show is somewhat unique as it was created by stars McElhenney and Howerton, and is mostly written by them (along with Day). I tend to ignore the first season of the show because, while there are hilarious moments, Devito had not yet joined the cast. For me, Frank is an essential part of The Gang and It’s Always Sunny in Philadelphia just isn’t right without him. The following are my top 20 episodes (including clips of classic moments from each).
The Gang Gets Invincible (Season 3, Episode 2)
The premise of this Season 3 episode is that (as in the film Invincible) the Philadelphia Eagles are holding open tryouts. The Gang sees this as an opportunity to get out of the bar and do something different, although not all of them are interested in trying out for the team. Dennis and Mac with their competitive streaks are obviously interested, and so is Dee, who wants to prove that a woman can play football. As for Charlie and Frank, they just want to tailgate the tryouts. Dennis, Mac, and Dee do about as well as one might expect but I think the best part of the episode is the tailgating shenanigans, which include Frank tripping balls, the appearance of Green Man, and some classic moments with the McPoyle family. There’s also the scene of Dennis thinking he’s a Football God when he is very clearly not.
The Nightman Cometh (Season 4, Episode 13)
This musical episode is so incredibly good that they turned it into an actual live show. “The Nightman Cometh” centers around The Gang preparing for and performing Charlie’s musical, which he has written in an elaborate attempt to get The Waitress to marry him. What It’s Always Sunny is able to do that most shows can’t is take something truly horrific (in this case, child sexual abuse) and make it darkly funny. The entire premise of Charlie’s musical is a not-so-thinly-veiled attempt to work through his own issues of abuse. This could easily go terribly wrong in the hands of lesser writers but, as Day (who co-wrote the episode with Howerton and McElhenney) explains in GQ‘s oral history of “The Nightman Cometh”:
Any time we deal with that kind of subject matter, I like to think it’s coming from a more intelligent place. A rape joke is not remotely a funny thing; a man writing a musical that he thinks is about self-empowerment, and not realizing that all his lyrics sound like they’re about a child being molested, is a funny thing. The joke is coming from confusion and misunderstanding, which are classic tropes of all comedy.
The highlight of the episode, for me, is “The Troll Toll.”
Mac and Dennis Break Up (Season 5, Episode 9)
The relationship dynamic between Mac and Dennis is one of my favorite things about It’s Always Sunny. This episode highlights their weird co-dependent relationship by having them go through the equivalent of a break-up. Dennis takes off to hang out with Dee and Mac moves in with Charlie and Frank, but Dennis and Mac’s break-up throws off the whole Gang dynamic. Also, they are still obsessed with each other, so it obviously doesn’t last long. One of the highlights of the episode is Dee getting an increasing number of cats stuck in her wall, but I think the break-up itself is the standout scene.
The D.E.N.N.I.S. System (Season 5, Episode 10)
Demonstrate value. Engage physically. Nurture dependence. Neglect emotionally. Inspire hope. Separate entirely.
These are the tried-and-true steps that allow Dennis Reynolds to get so many women. Dennis is unequivocally the worst person in The Gang (and they are all pretty terrible people). He treats women horribly and “The D.E.N.N.I.S. System” is a perfect example of how the show is able to make an absolute monster like Dennis actually hilarious and weirdly charming. The highlight of the episode is Dennis explaining his system to The Gang.
The Gang Reignites the Rivalry (Season 5, Episode 12)
I really like when The Gang gets dark and “The Gang Reignites the Rivalry” has some very dark moments. I mean, they literally poison people in order to win a flip cup tournament. This episode’s best moments come from Dennis, who returns to his old fraternity expecting to be worshipped as an alum only to be disrespected by the actives. As we all know, Dennis does not take well to being disrespected, and things go downhill from there. Also, Frank discovers the joys of Ritteral (i.e. Adderal) and any time Frank is on drugs it’s comedy gold.
The Gang Buys a Boat (Season 6, Episode 3)
The Gang is a mess on land, but in this episode they attempt to take their misadventures to the sea. With the money they made off of their successful Dick Towel venture, they decide to buy a boat, although The Gang (per usual) have different goals in mind. Mac and Dennis want to throw P. Diddy-style parties while Charlie and Frank are more interested in a Forrest Gump-style shrimping vessel. Neither side gets what it wants because they are only able to afford a hot mess of a boat that needs a ton of work. “The Gang Buys a Boat” is pretty hilarious throughout but it also gives us one of the show’s darkest moments: The Implication.
The Gang Goes to the Jersey Shore (Season 7, Episode 2)
As someone who is very familiar with the trashy mess that is the Jersey Shore, this episode holds a special place in my heart. In one of the few episodes where The Gang actually leaves Philly, they take a brief trip to the Jersey Shore where Dennis and Dee used to vacation as kids. Of course, the shore is not at all how they remembered it, and things take several dark turns along the way. Charlie has an interesting night with The Waitress, but the best part of this episode is, without a doubt, Rum Ham.
Sweet Dee Gets Audited (Season 7, Episode 4)
“This is dark…The darkest thing we’ve ever done.”
Frank and Dennis speak those words and, honestly, they’re pretty accurate. In “Sweet Dee Gets Audited,” The Gang attempts to help Dee out of a jam. She’s been caught scamming the government by claiming a false dependent (the baby she had as a surrogate), and in order to avoid getting audited—which would reveal Frank’s cooked books at the bar—The Gang ends up throwing a fake baby funeral for poor little Barnabas Reynolds. Also, there’s a dead dog. The whole thing is just so wrong, but it’s not surprising that even dead dogs and babies are funny on It’s Always Sunny in Philadephia. The episode also has one of the best intros of all time.
The Storm of the Century (Season 7, Episode 6)
This episode perfectly captures the chaos that ensues during every forecasted Nor’easter. I have lived through many of these and it’s always the same panic even though it often ends up being nothing (as it does in this episode). “The Storm of the Century” has so many classic moments that I don’t even know where to begin. There’s Frank looting during Hurricane Katrina, Dee in full panic mode, Dennis’s obsession with the large-breasted news anchor, the big-box store shopping experience, the Y2K bunker…the list is endless. However, I would be remiss not to mention another of Dennis’s complete sociopath moments trying to get some hot chicks to ride out the storm at Paddy’s.
Chardee MacDennis: The Game of Games (Season 7, Episode 7)
Where to begin with “Chardee MacDennis”? This episode follows The Gang as they play a game of their own creation, which is equal parts drinking game, physical and emotional abuse, and complete insanity. If I had to pick one episode to show someone who has never seen It’s Always Sunny, this is the one I would pick because it fully captures the chaotic evil energy of the show (and it’s just plain funny as hell). It makes my list for Dennis’s facial expressions in this clip alone.
The Gang Gets Analyzed (Season 8, Episode 5)
This might be my favorite episode of all time. I love episodes where The Gang interacts with a normal person (in this case, Dee’s therapist) because adding that outsider’s perspective really brings out exactly how fucked up each of their individual personalities is. When we follow The Gang in their own little world, it becomes easy to overlook just exactly how insane they all are. In “The Gang Gets Analyzed,” their crazy is on full display—and to a professional, no less. The best part of the whole thing is that the only reason they are all there in the first place is that they can’t come to an agreement about who should do the dishes. Each member of The Gang’s therapy sessions are hilarious, but Dee’s session is my favorite.
Charlie Rules the World (Season 8, Episode 8)
As someone who spends a lot of time playing video games, I absolutely adore this episode. I have lost track of how many times I’ve watched it and it never gets old. In “Charlie Rules the World,” The Gang discovers online gaming. Dee, Charlie, Mac, and Frank get really into it but Dennis can’t stand it. He thinks it’s a waste of time and instead seeks out real-life experiences (some of which are…interesting to say the least). “Charlie Rules the World” has endlessly quotable lines and probably the most perfectly bizarre ending of any It’s Always Sunny in Philadelphia episode. Not surprisingly, Frank is pretty good at playing the game.
The Gang Dines Out (Season 8, Episode 9)
This is another great Mac/Dennis relationship dynamic episode that really leans into the whole “bickering married couple” angle that It’s Always Sunny likes to play with when it comes to these two characters. The whole episode takes place at Guigino’s, the fancy Italian place frequented by The Gang. “The Gang Dines Out” is a perfect exploration of the interpersonal dynamics of the group as a whole and also of the “couples” (Mac/Dennis and Frank/Charlie). Then there’s Dee, all on her own as usual, just trying to use her Groupon before it expires. This episode has a pitch-perfect ending but it is funny all the way through, with the weird feud between Mac/Dennis and Frank/Charlie taking center stage.
Reynolds vs. Reynolds: The Cereal Defense (Season 8, Episode 10)
As if we didn’t have enough evidence that Dennis is a complete sociopath, in this episode we discover that he eats cereal while driving. This, predictably, has disastrous consequences when Frank rear-ends him, leading to The Gang holding a mock trial at Paddy’s to decide who is at fault. There are a lot of classic moments in this episode, but Mac’s elaborate attempt to discredit the theory of evolution is far and away the best part.
The Gang Broke Dee (Season 9, Episode 1)
Kaitlin Olson does not get nearly enough credit for how amazingly talented she is. In “The Gang Broke Dee,” Olson is at the top of her game. Dee is horribly depressed, which isn’t fun for The Gang because they can’t enjoy berating her when she’s not fighting back. The episode starts pretty dark and only gets worse, with a twist ending that is so horribly cruel and funny that I won’t spoil it here. The episode intro really sets the tone for the whole thing.
The Gang Tries Desperately to Win an Award (Season 9, Episode 3)
This episode is an incredibly meta take on the fact that It’s Always Sunny in Philadelphia has itself never won any awards. It’s inconceivable to me that they aren’t consistently nominated in every single comedy category. In an attempt to win the Best Bar in Philadephia award, The Gang goes to a local award-winning hotspot and decides to copy every single thing that they do there. Any attempt by The Gang to act like normal humans is always a failure, but their attempt to emulate the cheesy banter of the waitstaff at Sudz is absolutely hilarious. To no one’s surprise, things don’t go well, and the episode ends with a classic Charlie musical number.
The Gang Beats Boggs (Season 10, Episode 1)
I love it when The Gang gets shitfaced, and they have never been drunker than they are in “The Gang Beats Boggs.” The premise of the episode is that The Gang is trying to beat Wade Boggs’s drinking record: 64 beers on a cross-country flight from Boston to Los Angeles. The Gang is really committing to the contest, actually booking a flight together and bringing their own beer for when the plane inevitably runs out. Mac is the only sober one, taking on the role of “commissioner” to judge the contest. There’s some mile-high-club action and, as is wont to happen on It’s Always Sunny, somebody gets poisoned. Dee’s drunken slurring and commandeering of the PA system (à la Kristen Wiig in Bridesmaids) is a high point, but I have a soft spot for Charlie and his chicken.
Charlie Work (Season 10, Episode 4)
A health inspection at Paddy’s Pub: what could possibly go wrong? The answer is, obviously, everything. “Charlie Work” is one of those episodes where Day’s manic comedic energy really shines. Charlie attempts to get The Gang to take the inspection seriously while they are in the middle of one of their ridiculous schemes (this one involves live chickens), and the results are predictably hilarious. Charlie is often the butt of everyone’s jokes and is considered the least intelligent one of the group, but in “Charlie Work” we see that he is actually incredibly competent. He’s forced to think on his feet and problem-solve in a very high-pressure situation and he does so successfully. The whole episode is genius but the opening sequence stands out and sets the frenetic pace of the episode:
Chardee MacDennis 2: Electric Boogaloo (Season 11, Episode 1)
“Chardee MacDennis” was so funny they did it twice. In the second installment of everyone’s favorite game, The Gang is trying to sell Chardee MacDennis and invites a board game executive to Paddy’s to demonstrate the gameplay. This game of Chardee MacDennis features three teams, with Frank and the executive playing against Dennis & Dee and Mac & Charlie. If you thought things got out of hand the first time The Gang played the game, this time takes the cake. The episode ends in that dark, twisted territory It’s Always Sunny likes to frequent, even going so far as to include elements of horror. But things don’t get super dark right away; the gameplay has its lighter moments, including Glenn Howerton’s full-Philly accent.
Mac and Dennis Move to the Suburbs (Season 11, Episode 5)
I quote this episode at least once a day (“Newsflash, asshole!; “Seize the goddamn gap!”). If you have never lived in the ‘burbs, you may not fully appreciate the absolute genius of “Mac and Dennis Move to the Suburbs.” It perfectly captures all those little frustrating things that can add up and make a person absolutely snap—and snap they do. Mac and Dennis’s relationship dynamic is always a bit strained, but take them out of Philly and things escalate quickly. Never has the Mac/Dennis-as-married-couple gag been so thoroughly and deeply explored as it is here, and this marriage does NOT end well. The suburban-life montage set to Gnarls Barkley’s “Crazy” is painfully relatable (except for the dark-even-for-Sunny portion with the dog, which is maybe the most upsetting thing the show has ever done).
I could keep going forever when it comes to great episodes of It’s Always Sunny in Philadephia. There are plenty of episodes I love that didn’t make this list, including everything related to the McPoyles and the Ponderosas, and some of last season’s episodes that I just haven’t had a chance to watch enough times yet for them to become favorites. If you’re a fan of the show, we’d love to know what your favorite Sunny episodes are so let us know in the comments or on social media. Until then, can I offer you a nice egg in this trying time?