It’s Always Sunny in Philadelphia is now the longest-running live-action comedy show of all time, an impressive feat considering its humble beginnings. Despite its long-standing success, no other series has managed to replicate its formula, although perhaps they may be too scared to try. The humor in It’s Always Sunny is predicated on the audience’s understanding that they’re watching a series with no interest in redemption arcs or lesson-learning for its characters.
In 2021, It’s Always Sunny put out its 15th season, and FX has already renewed the series through season 18. Most series reaching such a milestone would see an understandable downturn in quality, but for It’s Always Sunny, for the most part, that hasn’t been the case. Sure, while creating this list there were certainly some seasons with more standout episodes to choose from, but there was always more than one episode to choose from when deciding what each season’s strongest outing was. Here are the best episodes from each season of It's Always Sunny.
“Underage Drinking: A National Concern” (Season 1, Episode 3)
Kaitlin Olson famously campaigned for Dee Reynolds to be just as depraved as the rest of the guys in the group. It’s episodes like this one that make it clear why she got her wish. This episode is the first to show the entire gang being equally slimy, as they allow high schoolers to drink at their bar because it’s good for business. Dennis (Glenn Howerton) and Dee become embroiled in teenage love affairs, while Charlie (Charlie Day) just becomes embroiled in the drama. Mac (Rob McElhenney) has no real issue with his friends dating high schoolers and is mostly just jealous that none of the said adolescents think he’s cool.
“Dennis and Dee Go on Welfare” (Season 2, Episode 3)
Not many other shows would have two of their main characters become addicted to crack, but that’s the type of storyline It’s Always Sunny makes light work of. When Dennis and Dee try to manipulate the welfare system to avoid work, they go so far as to buy crack cocaine in order to fit the bill. Meanwhile, Charlie has his hands on Frank’s money, which the latter put in Charlie’s name in order to keep his wife from getting her hands on it, leading to Charlie and Mac purchasing tuxedos, a limo, and a whole lot of sex workers and booze. Of course, Frank (Danny Devito) gets wise to the activity on his account and shuts it down before Mac and Charlie can actually pay for any of this.
“The Gang Gets Held Hostage” (Season 3, Episode 4)
Not only a highlight for the entire gang but a McPoyle highlight as well. Everything about this episode works and is a sign of the show really hitting its stride. Frank is terrified that Dennis and Dee are going to kill him in order to gain their inheritance, and with Charlie’s paternity in question, he also stands to gain from Frank’s hypothetical death. While this is being worked out via walkie-talkie communication and Frank crawling through the vents at Paddy’s Pub, the McPoyles burst in, intent on holding the gang hostage. The McPoyles turn up the heat (literally), no one quite understands what Stockholm Syndrome is, and the gang cracks under pressure pretty quickly. The anticlimactic ending is the hilarious cherry on top of this soupy sundae.
“The Nightman Cometh” (Season 4, Episode 13)
Charlie, who you may recall is illiterate, writes a musical and casts the rest of the gang as the Dayman (Dennis), a barista princess (Dee), a troll (Frank), and the Nightman (Mac). This is all a ploy to profess his love to the waitress (Mary Elisabeth Willis), but none of his friends are doing quite what he wants. Dee is deeply uncomfortable with her character's seemingly sexual desire for a young boy (played by her brother), and Frank can’t stop saying “boy’s hole” instead of “boy’s soul.” And Mac insists on doing karate onstage. Not only is this the best episode of the season, but this commitment to a ridiculous bit makes for one of the most beloved episodes of the entire series so far.
“The Gang Gives Frank an Intervention” (Season 5, Episode 4)
On It’s Always Sunny, characters are their best when they’re at their worst. Over the seasons, we’ve seen each character get pretty low, but “The Gang Gives Frank an Intervention” is one of the series's best outings in that regard. When Frank’s behavior gets sloppy enough that he’s trying to bang his dead wife’s sister, Dennis, Dee, and Charlie decide that he needs an intervention. Mac decides that he needs to beat him to it. The gang brings in a therapist to help with their intervention, and her inclusion and responses to their antics elevate just how insane they’ve become. Their intervention starts with everyone getting drunk on wine in cans until Frank shows up, led there by a false claim of a fire in the bar (for which he brings his gun). This is an episode that ramps and ramps, and never gets to be too much. It’s a big, hilarious, wonderfully-written and acted mess.
“Who Got Dee Pregnant?” (Season 6, Episode 7)
When a television show does an episode where each character tells their version of events in order to solve a mystery, you’re pretty much guaranteed a good time. In “Who Got Dee Pregnant?”, Dee is tired of everyone bullying her for gaining weight, so she angrily tells them that she’s pregnant, which none of her friends have noticed. She insinuates that one of them is the father, leading the guys to spend the entire evening trying to piece together the night of the Halloween party, which they believe to be the night Dee got pregnant. Everyone’s account of that night is what you’d expect, but that’s what makes it so funny: Charlie remembers kissing the waitress, Dennis remembers hooking up with the hottest girl at the party, Mac remembers heroically winning a fight, and Frank remembers arguing with Artemis about whether they should have sex in a dumpster (again).
“CharDee MacDennis: Game of Games” (Season 7, Episode 7)
Sometimes, a series will introduce a new “old” thing, and it just doesn’t work. It can feel contrived and raise questions as to why we haven’t seen it before. This is not one of those episodes. Of course, the gang created their own board game for slow days at the bar, and of course, the prize for winning is simply humiliating the losing team. Having the gang explain the game to Frank is a useful tool in showing how this game really only makes sense for them to play. Who else would write a rule where cheating is encouraged, but only punished if caught? Who else would have a competition that involves throwing darts at their friend’s hand? Who else could make it all this funny?
“The Gang Dines Out” (Season 8, Episode 9)
Continuing on the theme of “who else could do this?” is the next episode: Who else could turn seeing your friends at a restaurant into a complicated power play about “paying tribute?” Aside from the hilarity of this excellent bottle episode, “The Gang Dines Out” may just be the nicest we’ve ever actually seen the gang be towards each other.
Dennis soothes Mac’s insecurities about their friendship by serenading him in front of the entire restaurant, and we learn that Charlie and Frank celebrate the anniversary of their moving in together. But the sweetest moment (in It’s Always Sunny terms) comes at the end, when Dee, dining alone, breaks up what’s about to be a fight between the rest of the gang by tying a waiter’s shoelaces together and causing him to trip and spill a plate of spaghetti. This act earns her a rare stamp of approval from her friends, who end their night enjoying each other’s company (and ruining everyone else’s).
“The Gang Tries Desperately to Win an Award” (Season 9, Episode 3)
Otherwise known as “The Gang Gets Meta”. Despite its successful run and devoted fanbase, It’s Always Sunny has been ignored by all the major prestige television awards. The writers address this in an episode that has the gang declaring that they couldn’t care less about Paddy’s Pub winning any awards before doing all they can to do just that.
In order to do so, the gang spies on another bar, clearly modeled after the sort of sitcoms that do win awards. This bar features bright visuals, will-they, won’t-they subplots, and female characters that don’t need to be funny because they’re likable and cute. The gang decides to try their hand at this, but bright colors look garish in their dingy pub, and Mac chokes Dee when she tries to flirt. Frank’s burlesque club in the office and Charlie’s “fuck you” serenade solidify the fact that the gang has no intention of changing.
“Charlie Work” (Season 10, Episode 4)
The camerawork on It’s Always Sunny is solid, but not often a focal point. 10 seasons in, and the series goes for a special Charlie episode that follows Charlie doing his best to get the bar ready for an impromptu health inspection in an episode that gives the appearance of being done in one shot. Aside from the inspired camerawork that keeps the viewer locked in with Charlie and heightens his sense of urgency, this is just another hilarious episode of It’s Always Sunny. Charlie is in the rare position of being the most responsible member of the gang, and he has to basically wrangle his friends in order to pass the health inspection.
“Mac and Dennis Move to the Suburbs” (Season 11, Episode 5)
It’s Always Sunny is great at handling running gags. The show never beats its audience over the head with these recurring jokes, but instead remembers them from time to time, occasionally bringing them to the forefront for a worthy storyline. In “Mac and Dennis Move to the Suburbs,” Dee has had enough of the guys crashing at her one-bedroom apartment, so the two get a place out in the suburbs. Mac and Dennis love each other, sure, but it’s always funny to remember that Dennis also kinda hates Mac. At the very least, he finds Mac very, very annoying, and this dynamic plays out beautifully as the two enact some sort of romantic thriller. Their stubborn refusal to lose a bet with Frank means they can’t leave, so the two slowly go insane.
“Hero or Hate Crime?” (Season 12, Episode 6)
Most shows would have one of their main characters come out to their friends over the course of an emotional episode. But this is It’s Always Sunny, so Mac finally comes out over a lottery ticket dispute with Frank (For the record, there is an episode, “Mac Finds His Pride,” that does give a bit more weight to his coming to terms with his sexuality.) Just as Frank uses a homophobic slur to save Mac’s life, Mac finds a lottery ticket (dropped by Dee, who bought it with Dennis’s money). What follows is a dispute over who the ticket should belong to, and a whole lot of airing of the gang’s dirty laundry, including Dee and Charlie confessing that they’ve taken up smoking, and Dennis’s attempted grooming of a young woman through Dee.
“Times Up for the Gang” (Season 13, Episode 4)
How on earth was the gang, made up of five people with horrible attitudes about women, going to adapt to the #MeToo era? The answer is, of course, that they won’t, but it’s fun to watch them sweat (literally) in “Times Up for the Gang.” At a seminar about sexual misconduct in the workplace, each member of the gang is confronted with their own gross behavior.
Opening remarks have barely begun before Frank is calling his lawyers to ask about statutes of limitation, and Mac and Dee are surprised to learn that being gay and being a woman does not automatically prevent you from engaging in sexual misconduct. No amount of PowerPoint slides can teach Charlie that stalking isn’t romantic, but Dennis has words of comfort for them all: they don’t have to change. They just need to learn to be sneakier about their bad behavior, like he is. While maintaining the status quo for the show and its characters, this episode nails the behavior and attitudes of sexual predators while providing some relief through comedy.
“The Janitor Always Mops Twice” (Season 14, Episode 6)
It’s honestly surprising that an episode like this didn’t come sooner, but regardless of timing, “The Janitor Always Mops Twice” is a standout. A black-and-white film noir take on the mystery of Frank getting “diarrhea poisoned” lets the gang flex their best impressions of fast-talking criminals and detectives in what’s clearly another one of Charlie’s elaborate fantasies. Perhaps the highlight of the episode is the adaptation of the gang’s constant put-downs of Dee, who clearly wants to be seen as “a knockout blonde with a body that would make a statue blush.” Instead, the guys can’t help but see her as a goon - “You’re giving off big goon vibes, Dee.”
“The Gang Carries a Corpse Up a Mountain” (Season 15, Episode 8)
It really is kind of amazing how good this show continues to be. The season finale of season 15 is the strongest of the latest season and proves that the show is still going strong. Once again, an episode centered around an absurd premise (Charlie asks his friends to help him carry his father’s body up a mountain to be thrown off of a cliff as per family tradition) shows how awful each character can be, but also their dedication to one another and their bond at the end of the day.