25. Mac and Dennis Move to the Suburbs (s11e5)
“Newsflash, asshole! I’ve been hearing it the entire goddamn time!”
Losing your mind after a move to the country might not be the most original plot, but Mac and Dennis do it so well it feels new. I’ll take any opportunity to watch Glenn Howerton explode, and this slow build toward madness makes for what is probably his best explosion ever. I don’t usually like an imbalance of participation from the gang, but in this case the long stretches of Mac and Dennis alone are vital to the mood, and I think they’re very much worth it. Besides, Frank and Charlie’s mysterious Russian hat scheme is a beautiful gag that could only work from a distance.
24. The Maureen Ponderosa Wedding Massacre (s8e3)
“What are you doing? Are you doing the speech from Jaws?”
As far as genre episodes of Always Sunny go, this is the most successful. “Massacre” isn’t a parody of a horror film… it is a horror film. And with the utterly bizarre McPoyles involved, it’s ambiguous just how real all the horror elements are. It turns out there’s a reasonable(ish) explanation for everything, but at the time the terror is really palpable. It’s an episode so exciting and strange that Guillermo del Toro’s wonderful guest spot as Pappy McPoyle hardly even stands out.
23. The Gang Dines Out (s8e9)
“Yeah dude, Charlie’s looking right at me.”
Sometimes all a script needs to work is an artificial barrier between the characters. And what better barrier than one in the gang’s own minds, as for reasons unknown they settle into a Godfather-esque standoff. Charlie and Mac’s extended eye lock across the room is very high on my (as yet unwritten) list of the show’s funniest scenes. It’s also a rare episode when the gang show real affection for each other. Frank has prepared a heartfelt speech for Charlie on their anniversary. Dennis serenades Mac. And everyone, in a moment that may never have been seen before or since, thinks Dee is funny and salutes her. It’s a bizarre and sweet standalone episode that uses its self-imposed constraints to full effect.
22. The Gang Beats Boggs (s10e1)
“It’s Wade Boggs style.”
Bottle episodes are great — they force the gang together to interact in unpredictable ways. And there’s nothing quite like being stuck on a plane. But while the enclosed space breeds anxiety in the viewer, it winds up being almost incidental. Because this is an episode virtually without conflict. (Notwithstanding the frat boy Frank may have murdered, but who’s counting deaths?) All we’re counting here is beers, as the gang engage in one of their more sublime just-for-the-hell of it pastimes. They are not flying to LA to see a baseball game. They’re not flying to LA for anything. They just want to recreate a glorious moment in history, and they’ve bought five round-trip cross-country plane tickets to do it. All they want is to honor the memory of Wade Boggs, who is in fact so alive that he guest stars as his own ghost. The gang may ruin a flight for a plane-full of people, but by their own logic Charlie achieves the impossible dream, and we can’t help but root for him. “Boggs” is a joyful, heartening celebration of life, and of achieving something great just because you feel like it.
21. The Gang Group Dates (s10e2)
“I’m a five star man!”
Is it immediately evident that the words ‘rate’ and ‘rape’ are only one letter apart? Probably not. But once Dennis announces that he will “rate every single woman in this restaurant,” it sure is. “Group Dates” is a surprisingly subtle look at the double standards to which men and women are held for their sexuality. When the women he dates are given even a modicum of the power he usually wields over them (or, more accurately, when he becomes aware of their potential to wield that power), Dennis goes absolutely insane. Does he learn anything from it? God no. And neither does Dee, whose attempts to empower herself backfire when she misjudges the male standards she’s being held to. That’s because this is Always Sunny, and in the end the best the gang get is a moving speech about the importance of self-deception. But while they may not have grown, we as the audience have, with one of the show’s finer examples of pure, hilarious, conscientious satire.
20. Mac and Charlie Die Part One (s4e5)
“Of course it’s gonna be with class! You think I’m not gonna die with class?”
Mac and Charlie have been friends since childhood, and when they team up there’s a certain childlike logic you don’t see in any other pairings. And that wonderful, stupid, seat of your pants thinking is in top form when they try to fake their own deaths. Their increasingly unhinged attempts to destroy Dee’s car so the police will think they’ve been vaporized in it are absolute gold. Every dumb new take on the plan is fully embraced, and no one’s really in charge as Charlie discovers his teeth come right out of his head, Mac becomes obsessed with a pawned wedding dress, and both get addicted to poppers. It’s an episode that does stupidity and chaos very, very well.
19. CharDee MacDennis: The Game of Games (s7e7)
“Gentlemen, suck my dick.”
It’s always fun to see the gang navigate the wide world, but some of the finest episodes are completely within the confines of their circle, where bizarro logic reigns supreme and is corroborated five times over. This plays extremely well with CharDee MacDennis, a game of arbitrary and obtuse rules that everyone agrees they have to adhere to unflinchingly. It’s an expert stroke to make Frank the fish out of water, our focalizing point for learning the rules of the game. By season 7 it’s hard to think of him as an outsider still, but it’s a necessary and wholly logical tweak. It’s also a lovely spin on the gang’s usual attempts to explain their logic to other people, as Frank is the most willing participant they’re ever going to find. It’s a wonderful, fun episode that makes you appreciate the gang’s dynamic and, just once, actually wish you had friends like them.
18. Time’s Up for the Gang (s13e4)
“Now you may ask, ‘Would a woman really text that, Dennis?’ …Their phones did.”
With well-established terrible characters, Always Sunny is in a choice satire position, able to address any hot button issue by turning the gang loose and letting them riff on it for 20 minutes. This method worked fabulously last year with language and “Hero or Hate Crime?,” and the same formula pays off again this year with sexual misconduct and “Time’s Up for the Gang.” I wrote a much longer breakdown of the episode here, but in short, what makes “Time’s Up” so good is its ability to tackle such a progressive subject while keeping the gang decidedly unprogressive. It’s a line the show is very skilled at walking, and this episode walks it on a whole other level, with the master stroke of making Dennis the rational voice, but for all the wrong reasons. It’s those wrong reasons that keep the episode feeling so true to Always Sunny, and that manage, just maybe, to trick a large portion of the fans into appreciating a conscientious message in spite of themselves.
17. Reynolds vs. Reynolds: The Cereal Defense (s8e10)
“Until another smartest guy came around. Galileo. And he disproved that theory. Making Aristotle, and everybody else on earth, look like a… BITCH.”
Internal arbitration with the gang is a wonderful thing, and nowhere does it shine brighter than with the court case of the century. Their grip on what a trial actually is is a little shaky. There’s no judge. There’s no jury. It’s not clear who the defendant is, and everyone wants to be the “persecutor.” But by God they make some compelling arguments. Mac’s take-down of evolution is convincing stuff, and beautifully far gone from the issue at hand. The moment a regular customer finishes his drink and takes off for the day is a fantastic touch. There’s rarely a scene without at least one barfly in the background, but the reminder that this deeply complex inanity is taking place in the middle of a working business, as it is every time, is still hilariously jolting.
16. Who Got Dee Pregnant? (s6e7)
“YOU WILL CALL HER!”
Working pregnancy into tv shows has always been an issue. Just how many improbable babies did the women of Friends have, anyway? It’s especially hard when the characters aren’t at a point in their lives when having a baby makes much sense: case in point, Sweet Dee. The show handles it beautifully, though — for half a season of loose-fitting shirts and carefully placed towels, it’s never even mentioned and the audience is none the wiser. Then out of nowhere, Dee is very visibly pregnant and, it’s revealed, has been talking about it for some time now. We just haven’t heard anyone say anything because no one cares. Only when Dee tells the gang that one of them is the father do we get a whole episode devoted to the issue. It’s classic Always Sunny treatment, and it’s a lovely solution. It also makes for a genuinely fantastic Rashomon-style episode of pieced together memories in which we get to see how each member of the gang sees themselves and how they fit into the group… At least when they’re brown out drunk. The fact that Mac sees Dee as a screaming ostrich is an outrageously good touch. (Particularly since that is, in reality, Rob McElhenney’s baby). And the gang’s brief conviction that it’s Dennis who’s gotten his twin sister pregnant is truly horrifying. It’s short-lived, but the fact that it’s entertained at all is a fantastic testament to the show’s use of the grotesque, especially around something usually so sacred on other tv shows. It’s a fantastic episode that gives a perennial actors’ issue its own bizarre treatment and makes a complex, profoundly funny whodunit in the process.
15. The D.E.N.N.I.S. System (s5e10)
“Whoops. I dropped my monster condom that I use for my magnum dong.”
This is one of the show’s most beloved classics, and it deserves it. An early glimpse into Dennis’ complete lack of empathy, it’s also an unsettling look at how willing the gang are to go along with him. But God, is it funny. The delicate ecosystem, in which Mac and Frank apparently swoop in and sleep with the women Dennis has abandoned, is astoundingly creative. It’s with these revelations of the complex structures forever lurking under the surface that the show is at its best. The episode culminates, as it must, with the rest of the gang grossly misunderstanding Dennis’ system and ruining everyone’s efforts. And while this is Dennis at an unprecedented level of despicability, you still feel a twinge of empathy for him as no one else can grasp the nuance of his art. Or at least I do. Maybe Dennis and I have more in common than I’d like to admit.
14. The Waitress is Getting Married (s5e5)
“Little green ghouls, buddy!”
Whenever I’m trying to get someone to watch Always Sunny, I lead with Charlie’s dating profile. It is, I truly believe, one of the most universally funny things in existence. The entire episode is a gem. From Dee’s miserable bachelorette party to Charlie’s miserable date, it’s cringe humor at its best. And unlike so many episodes, it has a satisfying, almost uplifting ending as Charlie gets revenge on the man who’s broken the Waitress’ heart and is about to break Dee’s. We all know that box is filled with hornets. It’s a good thing he popped a quick H on it, after all.
13. The Gang Gets Analyzed (s8e5)
“We’ll make an adjustment to it, and we’ll make a tradition out of it.”
This episode is a gem. A showcase of the gang’s foibles, a longform effort to explain something to an outsider, and an extreme reaction to a small problem, it’s a confluence of some of Always Sunny’s finest tropes. Kerri Kenney plays the perfect straight man, horrified by the gang’s dynamic but actually able to make progress with some of them. Everyone’s individual session is a beautiful look at what makes them tick, a stark contrast between things we’ve taken for granted and a cold medical perspective. But while the sessions feel very true to the gang, they still manage to be surprising and outstandingly creative. Frank’s haunted memories of youth in particular come on so suddenly and from so far out of left field that it’s downright disorienting. The episode wraps perfectly, with Kenney finally breaking down and ordering Dee to do the fucking dishes. The gang are a powerful force, and not one easily overcome.
12. Sweet Dee Has a Heart Attack (s4e10)
“That right there is the mail. Now let’s talk about the mail. Can we talk about the mail, please, Mac? I’ve been dying to talk about the mail with you all day, okay? Pepe Silvia! This name keeps coming up over and over again. Every day Pepe’s mail’s getting sent back to me. Pepe Silvia, Pepe Silvia. I looked in the mail, well this whole box is Pepe Silvia! So I say to myself, I gotta find this guy. I gotta go up to his office, I gotta put his mail in the guy’s goddamn hands, otherwise he’s never gonna get it. He’s gonna keep coming back down here. So I go up to Pepe’s office and what do I find out, Mac? What do I find out? There is no Pepe Silvia. The man does not exist, okay? So I decide awww shit buddy, I gotta dig a little deeper. There’s no Pepe Silvia? You gotta be kidding me. I got BOXES full of Pepe!”
This episode is a classic in every sense of the word. It may be the epitome of solid, well-crafted, still-early Always Sunny insanity, when the characters really start to lose it and the show hits its stride. Everyone begins with a reasonable goal in mind: staying healthy. But the descent into madness is swift, grotesque, and very deliberately cinematic. Frank winds up in a straight recreation of One Flew Over the Cuckoo’s Nest (Danny DeVito’s very first movie role) complete with Tim Sampson, the son of Will Sampson, the actor who played Chief in the original. There are no jokes in this storyline — it simply is. It’s played for the thrill of familiarity, and for the comic audacity of just plunking an actor in one of his old films. It’s a great sign of the artistic risks the show will later be willing to take. But the real gem, of course, is the mailroom storyline, where Mac’s dreams of recreating The Secret of My Success are derailed by Charlie’s descent into A Beautiful Mind madness. Born out of Charlie’s addled reading of “Pennsylvania,” it gives us one of the show’s best monologues, and one of its most-loved memes. It’s pure gold.
11. Mac Day (s9e5)
“You know what’s badass? Being alive.”
Ostensibly this is another great look into the myriad rules the gang have decided to live by — each member gets a designated Day to impose their will on the others. It’s a fantastic concept. But rather than just being played for laughs, “Mac Day” affords us with some real character development. Maybe not for Mac himself, whose greatest defining characteristic is denial, but for the audience, who get to see the full extent of that denial and how it reflects upon his friends. Seann William Scott as Country Mac is an inspired addition, representing all the things City Mac would or could be but isn’t. And his death is the perfect end cap — the gang can reflect on how he wasn’t quite as awesome as he seemed, and City Mac can reign uncontested with his mess of delusions that seem just a little sadder and more profound now. RIP Country Mac. I’m sure you’re not actually burning in Hell.