The 25 Best It's Always Sunny In Philadelphia Episodes, Ranked
In August of 2022, a clip from the "It's Always Sunny in Philadelphia" 2009 episode "The Great Recession" went viral. It was the scene where Mac and Dennis realize that Paddy Bucks, their self-created currency designed to beat the nationwide economic downturn, is a sham that they don't even understand. To call it funny is an understatement. It was attached to a tweet about crypto investors and the failing crypto market of 2022; to call the Paddy's Bucks clip prophetic is also an understatement.
This is the lasting appeal of Rob McElhenney, Charlie Day, and Glenn Howerton's groundbreaking FXX show in microcosm. The half-hour comedy primarily set at Paddy's Pub is about the worst people on Earth (Mac, Charlie, Dennis, Sweet Dee, and the latter two's father, Frank). They do reprehensible things with startling frequency. Within their consistent awfulness, though, is an equally constant incisiveness about toxic masculinity, white supremacy, social structures, and the human condition at large. Paddy Bucks are just the tip of the comic iceberg.
So even if it proves disastrous, we're attempting to rank the 25 best episodes of "It's Always Sunny in Philadelphia," one of the best TV comedies to ever air. I promise to be a wild card and wear kitten mittens throughout. Rev up your starter cars, finisher cars, and transporters of gods, because here we go.
25. The Gang Beats Boggs (Season 10, Episode 1)
"It's Always Sunny" isn't a show about baseball, but it is, occasionally, a great and singular baseball show. Two episodes on this list detail the gang's relationship with America's pastime and both approach the sport from oblique angles. "The World Series Defense" looks at a pivotal Phillies game and how wistful fandom quickly turns toxic. "The Gang Beats Wade Boggs" is about how athletes can inspire. Because it's an episode of "It's Always Sunny" and not, say, "Full House" or "The Big Bang Theory," the inspiration involves alcohol, naturally.
More specifically, 70 beers, which were (supposedly) drank by Boston Red Sox legend Wade Boggs set on a cross-country flight to L.A. The gang boards their plane to the West Coast and aim to topple his record. By "It's Always Sunny" standards, the debauchery that follows is less memorable than the show's A-tier. For all intents and purposes, it's a minor entry to the show. That's also why it's excellent. The leisurely pace of baseball feels like a North Star for the episode's gentle madness.
When Wade Boggs himself shows up in Charlie's drunken vision, it feels less absurd than it does welcome. That subtle tonal shift — plus Charlie Day's incredible performance as 71-beers-deep Charlie — earns "The Gang Beats Boggs" the honorary spot on this list. It knows how to play ball.
24. Chardee MacDennis 2: Electric Boogaloo (Season 11, Episode 1)
"It's Always Sunny in Philadelphia" isn't shy about sequel culture. The gang even makes a sequel to "Lethal Weapon." More importantly, some of the series' best episodes are follow-ups to fan favorites. What Rob McElhenney, Charlie Day, and Glenn Howerton seem to understand more clearly than many of their comic contemporaries is that the best sequels don't just expand and rebase the source material — they challenge what made it effective.
"The Last Jedi" picks apart the cultural reverence for "Star Wars" mythos. The recent smash "Top Gun: Maverick" is about the inevitability of facing extinction far more than it is a hyper-masculine triumph. "Chardee MacDennis 2: Electric Boogaloo," the follow-up to "Chardee MacDennis: The Game of Games," is an unflinching look at how the gang's games beyond this one are entirely dangerous for strangers; in this case, a Mattel executive named Andy (Andy Buckley). "Chardee MacDennis" is a madcap "It's Always Sunny" installment. "Electric Boogaloo" makes it look crazier retroactively.
How crazy? The first level of the game ("Trivia, Puzzles, and Artistry") involves Frank's very unfortunate team flag (four F's in a shape unnameable here), Charlie swallowing glass, and Dennis sculpting the image of a woman's head in a box. The episode's sight gags are stronger than its structure, which means it doesn't crack the series' top 20. But the truth it reveals about the gang makes it an essential part of the canon: They are dangerous to each other, but the boundaries of their fun and games they play with each other are implicitly understood. "Chardee MacDennis 2: Electric Boogaloo" makes it hysterically clear that's not true for anyone else.
23. Mac & Dennis Move to the Suburbs (Season 11, Episode 5)
"The Shining" is hardly a traditional touchstone for comedy, but "Mac & Dennis Move to the Suburbs" treats it like one all the same. That's why the Season 11 episode is beloved and memorable. It contains some of the finest work Glenn Howerton has ever done as Dennis, and director Todd Bierman stage horror beats that go far beyond "homage" status. When Dennis strips nude in broad daylight to confront his cheery neighbor Wally during the episode's third act, the moment is genuinely disquieting. Most of "It's Always Sunny" is a horror show if viewed through an objective lens, but this episode represents the program's breaking point with comedy. The suburbs shatter Mac, Dennis, and "It's Always Sunny" equally.
There's another sly reason, though, that "Mac & Dennis Move to the Suburbs" is an essential installment: the tacit character development of Philadelphia. The city of Brotherly Love is, as depicted in "It's Always Sunny," a place where professional sports teams demean their fans and the Most Dangerous Game can be played. It's also the only thing keeping Mac and Dennis' sanities intact. The suburbs break both men instantly, and this creative choice brings home once and for all that the gang needs Philly more than it has ever needed them. For them, maybe it is always sunny in Philadelphia after all.
22. Chardee MacDennis: The Game of Games (Season 7, Episode 7)
It's easy to forget that Danny DeVito hasn't always been a cast member of "It's Always Sunny in Philadelphia." Frank Reynolds is as essential to the gang as Homer is to "The Simpsons" or Kramer is to "Seinfeld" — a patriarchal male whose outdated views cause comedic chaos that trickles down onto the younger generation. Frank knows the Philadelphia his kids and their friends can't imagine. He's seen and done it all, and that's a creative boon for "It's Always Sunny."
That's also why "Chardee MacDennis: The Game of Games" is so lasting in its effectiveness and comedic force. For once, Frank has no idea what's going on. Frank Reynolds is the audience's surrogate for the Season 7 episode, in which a sadistic board game the gang made up is played to the hilt. The entire installation is one long set piece rich with classic hijinks (the war dance, the dart throwing sequence), and Kaitlin Olson's portrayal of inebriated Sweet Dee almost steals the episode.
But it is Frank Renyolds that makes "Chardee MacDennis" a classic. Whether it's Frank eviscerating the Chardee MacDennis rulebook or hanging out in an animal crate that serves as jail, the character is at his best because he's out of his element. It's a lane the show rarely swerves into, but it pays off on a top-tier level here. That makes it worthy of a spot on this list, even if it doesn't offer Frank at his most moving ("Mac Finds His Pride") or Frank at his most hysterical ("The Great Recession").
21. Wolf Cola: A Public Relations Nightmare (Season 12, Episode 4)
"Wolf Cola: A Public Relations Nightmare" is "It's Always Sunny in Philadelphia" at its most expansive. "Expansive" isn't a word one normally applies to deliberately crude sitcoms, but it applies here with force. The Season 12 episode bounces from Paddy's Pub to the Middle East, from the terrorist organization Boko Haram to the UFC, and from Wolf Cola to Fight Milk. More than anything, it reaches far and wide to put and keep the gang in the public eye.
For much of this episode's runtime, Dennis, Sweet Dee, and Frank attempt to assuage concerns about their terrible soda while Mac and Charlie further the financial prospects of their crow-filled beverage. By the episode's end, everyone has failed. The gang is an institution unto themselves, but when they meet other institutions in society (the news, or a massively popular combat sport), their insular logic crumbles like dust.
That's why Sweet Dee shatters any hope of Wolf Cola getting back on the public's good side by playing her idea of a CEO right before Dennis's anti-dog sentiments bury the hatchet once and for all. It's also why UFC President Dana White bans Charlie and Mac from the UFC forever. Public relations nightmares hinge on the public and, in "Wolf Cola," we learn once and for all that the public can't handle our crew. Plus, it features the series' funniest ever cold-open. It's an all-time great "It's Always Sunny" installment that's almost one of the 20 best.
20. Dee Gives Birth (Season 6, Episode 12)
"It's Always Sunny in Philadelphia," like many half-hour sitcoms before it, hasn't been shy about incorporating its cast's actual lives into the series' plot. But the FX show, arguably, has a longer leash to do so than almost any other on TV as its stars are the show's creators. So when Kaitlin Olson, who is married to Rob McElhenney, got pregnant, both chose to make Olson's pregnancy a season-long story arc.
The narrative culminates with "Dee Gives Birth," an episode that is not only one of the funniest "It's Always Sunny" has ever done but one of the sweetest. Every sequence of Mac, Charlie, and Dennis trying to become a good dad for Dee's impending child is priceless (Dennis banishing a nurse while invoking Thor is particularly giggle-inducing), but it's the ending that is peak "It's Always Sunny." The episode ends with Dee, newborn in her arms, being wheeled towards a cadre of Philly's worst humans, each of whom thinks they're the father, while a maudlin song plays. The child is played by Olson and McElhenney's actual son. The moment is legitimately moving.
Then the reveal occurs: Dee has been serving as a surrogate mom and leading men on throughout the season, manipulating them into sex and being, well, very Sweet Dee about being pregnant. The plot twist makes Dee's debauchery throughout Season 6 even more stunning retroactively and proves that even at its most sentimental, "It's Always Sunny" is a deliciously bleak look at what makes us human. Even if this isn't the funniest "It's Always Sunny" episode, that blend of sweet and cynical makes it a notch more important than the manic "Wolf Cola" or "Mac & Dennis Move to the Suburbs."
19. The D.E.N.N.I.S. System (Season 5, Episode 10)
Dennis is arguably the most fascinating character in "It's Always Sunny in Philadelphia," a would-be sociopath whose firebrand tendencies undermine his attempts to pass for high society. Dennis fancies himself a ladies' man and savant. He's neither. To his credit, though, he's often organized. The method to Dennis' madness comes front and center in "The D.E.N.N.I.S. System," which finds the eldest Reynolds child teaching the gang how he meets and picks up women (or, as Thought Catalog put it, "The BS women keep falling for").
It is hysterical watching them fail to do so instantly, as is Sweet Dee's B-storyline (the pratfall-punctuated scene in which Dee ruins a sweet picnic date through cynicism alone is an all-time favorite). Neither element is so fascinating as what the episode reveals about Dennis. By the time he's borrowing an elderly woman who can't stop talking about Susan B. Anthony to pose as his grandmother, it is clear that Dennis prioritizes success over anything that would make him a reputable boyfriend or reliable partner. The Dennis system, like Dennis himself, is fraudulent.
"It's Always Sunny" has never tired of finding ways to reveal this truth, but this is the show's sharpest ever reveal of it. Thankfully, it's also reliably funny. There are more hysterical Dennis episodes (and they're higher up this list, accordingly), but there might not be one that's more insightful or giggle-inducing in equal measure.
18. Hundred Dollar Baby (Season 2, Episode 5)
The gang has done no shortage of amoral acts throughout 15 seasons of "It's Always Sunny in Philadelphia." It's possible that "Hundred Dollar Baby" contains the most jaw-dropping one. The episode is largely a loose parody of Clint Eastwood's "Million Dollar Baby" that finds Dee taking boxing lessons after she gets mugged. Following her subsequent steroid addiction, Frank offers to box in her stead. When he does so, he cheats — and the daughter of Frank's old boxing rival, Brianna, winds up suffering the consequences of a snapped neck, not unlike Hilary Swank in "Million Dollar Baby."
So, to summarize: Frank gets a woman paralyzed or killed and his response is to scream an expletive and run away. This isn't the only time the actions of the gang necessarily result in death (the other would be "Charlie Goes America All Over Everybody's ***"), but it is the one where we most directly see the consequences of their selfish machinations.
This very dark, very funny "It's Always Sunny" episode belongs on the best-ever list because it provides a skeleton key to how the show softens its darkest plot twists. When in doubt, lean on parody or genre conventions. The reference to an Oscar-winning film disguises the actual depth of Frank's depravity, and savvy storytelling choices like it have likely helped keep "It's Always Sunny" on air for 15 seasons. For that reason alone, it deserves a spot in the middle of our list.
17. The Gang Gets Invincible (Season 3, Episode 2)
It'd be easy to pretend that a list of the best "It's Always Sunny in Philadelphia" would ever be objective in any way, shape, or form. Comedy is subjective. There's no way that this list wasn't going to include an episode that I find funnier than the average "It's Always Sunny" viewer, and, for me, that episode is "The Gang Gets Invincible." "Invincible" feels like an underrated football movie to sports fans. The "It's Always Sunny" episode about "Invincible" is equally slept on.
Yes, it's celebrated as the episode that gave the world Green Man. But it has as funny a cold open as the show has ever produced (a fight over rats vs. scorpions that leads to a meta dialogue about not filming episodes in Paddy's Pub anymore), and one of the greatest guest spots in the show's entire history. Faizon Love's sudden, repeated screams of "If I say it one more time" when getting the gang and company to board a football bus is as funny a comedic choice as ever committed to celluloid. I'm sure there are guest spots more valued by the public at large, but they're not writing this article. "The Gang Gets Invincible" is, yes, an invincible half-hour of sitcom gold. It deserves to make the team.
16. Mac Day (Season 9, Episode 5)
Some of the most brilliant "It's Always Sunny Philadelphia" episodes are primarily deep dives for one of the gang members, and that proves true of "Mac Day," which puts the spotlight on the most self-deluded member of the Paddy's Pub quintet. On a day devoted to doing whatever Mac wants, the gang is introduced to Country Mac (Seann William Scott), a rural version of their Philly friend that they instantly prefer to Mac himself.
Country Mac punks Philly Mac. He faces down a menacing knife-wielding thief and disarms him easily. By the episode's end, Country Mac has challenged and, in many cases, upended Mac's deeply held beliefs about himself. His death is a bleak and hysterical punchline that allows the show to maintain its status quo, but it is also a moment "It's Always Sunny" never looks back from.
In the wake of "Mac Day," Mac goes through a body image crisis and, later, finds his pride. Unlike so many of the gang, Mac proves capable of tangible, meaningful change. Given the emotional breakdown he suffers here, one could argue that "Mac Day" truly is a turning point for the character. That makes it not only one of the best "It's Always Sunny" episodes, but also the most series-changing. Even if it can't match the laughs of the previously mentioned "The Gang Gets Invincible" or "Chardee McDennis," it needs to be higher up the list accordingly.
If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.
15. The Gang Gets Analyzed (Season 8, Episode 5)
There are intellectual reasons to include "The Gang Gets Analyzed" on this list. First and foremost, the Luvh Rahke penned episode makes the revelatory decision to isolate each member of the gang with a psychotherapist (Kerri Kenney of "Reno 911" fame) instead of mounting an extended group session. It's rare to see Mac, Charlie, Frank, Dennis, or Dee one-on-one with anybody, let alone a trained mental health professional. Accordingly, "The Gang Gets Analyzed" is packed with revelations (Mac has body dysmorphia, and Dennis keeps files on his friends) that hint at why members of the show's dysfunctional found family keep choosing each other over actual stability. It's a lovely piece of incisive writing.
None of that even matters, though, in the face of Frank's confessional monologue. Frank's tales of life in a school for the mentally disabled, recounted to the therapist, are a comedy writing masterpiece. Four of the show's funniest lines ever are in this monologue. As strings well up behind him, Frank describes his first girlfriend ("She was always smiling ... because she had no lips. But her mouth was still very much in play") and her tragic death ("She thought she was a spaceman ... with a plastic bag for a helmet") in a torrent of operatic absurdity so sublime it should have netted Danny DeVito an Emmy.
Sometimes a show's best moments don't occur in their best episodes, but "The Gang Gets Analyzed" is a stunning exception to that paradigm. It teaches us about the series we love and adore before taking it to new heights.
If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.
14. How Mac Got Fat (Season 7, Episode 10)
Even TV viewers unfamiliar with "It's Always Sunny in Philadelphia" caught wind of the show in 2011 when star Rob McElhenney gained more than 50 pounds to satirize the trend of sitcom actors getting better looking the longer their shows were on the air. The creative stunt yielded McElhenney press from sources as disparate as TheWrap and Men's Health magazine. Looper also wrote about it in 2022. So there's zero doubt that Mac's weight increase worked as an attention-getting gesture. The question is: did it also yield riches creatively?
Simply put, yes. "How Mac Got Fat" is one of the 25 best "It's Always Sunny" episodes, the one chance the program's creative team had to stick the landing of McElhenney's bold body transformation and one they did entirely. In some ways, this is the best of the show in the microcosm. "How Mac Got Fat" makes a bold creative choice that it has to answer for, then zigs where other shows would zag.
The gang becomes convinced they've peaked and need to stop changing instantly for the status quo to remain. Dee hires avatars to take their place and Mac, as it turns out, gains his weight trying to match the lifting prowess of his avatar. Making McElhenney's transformation a cautionary tale of his character's frequent refusal to is the closest thing to a masterstroke this story could get, and the capstone of a near-perfect TV episode.
13. Who Pooped the Bed? (Season 4, Episode 7)
It wouldn't be a best-of "It's Always Sunny In Philadelphia" list without an episode that highlights The Waitress (Mary Elizabeth Ellis) or Artemis (Artemis Pebdani). Both are among the show's most essential recurring players and comic titans on the level of the gang themselves. Fittingly, there's an endearing "It's Always Sunny" episode that highlights the pair in equal measure: "Who Pooped The Bed?"
Did you laugh just reading that? The "It's Always Sunny" team is counting on that. "Who Pooped The Bed?" is the show at its most scatological, applying the program's sharp writing to a sophomoric subject. It's also proof that the show can elevate any subject without getting high-brow. That's the primary reason it's ranked so highly here; it's tempting to only acknowledge the moments when "It's Always Sunny" is a smart-stupid series, but genuinely stupid can be brilliant, too.
There are tons of hysterical cutaways to the aforementioned dookie that elicit ridiculous laughs each time they occur. There's also a highly scientific breakdown of the turd in question which yields the incredible line, "There is so much wolf hair in our apartment right now." When Artemis finally takes center stage for the episode's operatic third act, the proceedings truly soar. "It's Always Sunny" has always succeeded by relying on the gifts of its creative family, and it does so to memorable, not-crappy effect in this gross, great installment. It's not top 10 worthy, but it's close.
12. The World Series Defense (Season 5, Episode 6)
Whenever "It's Always Sunny In Philadelphia," tells us a story about Philadelphia, it is wildly successful. Case in point: "The World Series Defense," which looks at the Philadelphia Phillies' 2008 World Series win. Since "It's Always Sunny," the episode is mostly about the gang talking their way out of a World Series-related parking violation. We then learn what they tried to do for tickets to the game and what they suffered in the process.
How spot-on is that premise? In a tremendous piece titled "Resist The Darkness. Support Philadelphia," Tom McAllister describes two men in Philly fighting in the street after a 76ers loss, one with a knife and the other wielding a bat. Before they can kill each other, their mom and a group of people break them up. The two brothers were so drunk they forgot they were related, and they subsequently share a fresh beer. McAllister writes that "[Philadelphia] is always either developing a hangover or trying to cure one."
Now, look at what the gang endures the week of the Phillies' victory. Charlie throws Dennis in front of a moving vehicle while attempting to extort World Series tickets from the driver. They get trapped in tunnels while trying to sneak into the game. The Phillies' road to triumph is also the gang's path to failure. Our heroes can't get out of their way enough to enjoy a Philly victory with the rest of the city. That makes them Philly through and through — and that observation makes this an almost top 10 "It's Always Sunny" installment.
11. The Great Recession (Season 5, Episode 3)
It makes too much sense for "It's Always Sunny in Philadelphia" to do an episode about a recession because, on some level, every single "It's Always Sunny" episode is about trying to upgrade the gang and their economic status. Sometimes they are scheming for money. Other times, they're chasing clout (which will likely yield money). The not-so-buried lede of the FX show is that no one except Frank is well off and his wild supply of cash has origins so dubious they might as well be "The Twilight Zone." Why wouldn't the show nail an episode about a financial downturn?
Spoilers: it does. "The Great Recession" features some of the most quotable lines and moments in the show's history (Frank's repeated whispers of "It's a Ponzi scheme" live rent-free in my brain). The only thing keeping it out of the show's top 10 tier is the ridiculous humor highs of the best "It's Always Sunny" episodes and a relative lack of technical ambition.
But, as previously mentioned, the entire Paddy Bucks subplot anticipates cryptocurrency in chillingly prescient ways. There will always be versions of the gang out there in the U.S. of A, making a dime and then blowing it. They will capitalize on the weak and blow their shot. In "The Great Recession," the gang proves they're as hysterically American as apple pie.
10. The Gang Solves the Gas Crisis (Season 4, Episode 2)
"Wild card!" These two words alone can send "It's Always Sunny In Philadelphia" fans into hysterics. That's due to "The Gang Solves the Gas Crisis," an episode that turns Charlie into a self-proclaimed, Texas-accented agent of chaos who sabotages the gang's plans by design. Charlie has arguably been the most dangerous member of the gang since its inception (just ask the Waitress), but "The Gang Solves the Gas Crisis" makes the most convincing case yet. Charlie screams "wild card" before cutting the brakes of the gang's van. That's violence incarnate.
Memorable slapstick aside, the reason "The Gang Solves the Gas Crisis" is a classic is because it's an early "Sunny" episode that hones in on an essential stylistic balance. The more severe the issue "It's Always Sunny" is covering, the more ridiculous the show should be. Every episode following "Gas Crisis" that leaned into ridiculousness when satirizing institutionalized misogyny, race relations, and the second amendment, to name a few, was better for having gone broader.
"It's Always Sunny In Philadelphia" is a smart, stupid show. That's by design. With "The Gang Solves the Gas Crisis," they perfected the balance between those two polarities and every episode that ranks higher than this one reflects that. Wild card indeed.
9. Mac and Charlie Die, Part 1 & 2 (Season 4, Episodes 5 and 6)
For all that depravity that defines "It's Always Sunny In Philadelphia," there's also a remarkable amount of innocence, which is part of what makes the show so distressing. It recognizes, beyond a shadow of a doubt, that the line between naivete and concentrated toxicity is razor thin. Take "Mac and Charlie Die." It's one of the show's first ambitious efforts (witness the two-part format) and a triumph of character study and development.
Its story hinges, primarily, on Mac and Charlie being so misguided that they bounce from devious to endearing and back again in their attempt to fake their deaths and live like hobos from then on. These two frequently conspire to cause harm and, yet, their capacity to bounce through life like uninvolved parties is remarkable.
Take Concussion Mac, the head trauma-riddled version of Mac. Mac's pain reveals the kinder side of his self-deluded blowhard tendencies. Take The Shadow, a joke which is too good to spoil here but absolutely builds on this thesis. The gang is some of the worst people on the planet, but there is always hope they'll be better; "Mac and Charlie Die" makes this crystal clear. For all this episode's awfulness, it's a near-feature-length testament to the endearing qualities of their humanity that keep us watching. Unlike funnier episodes lower on this list, it revels in what makes Charlie and Mac worthy of our time. We're lucky, by episode's end, that they're still alive.
8. Gun Fever Too: Still Hot (Season 9, Episode 2)
"Gun Fever Too: Still Hot" begins with Frank pulling two pistols out of his pockets on live television while shelling for a local arms dealer and ends with Frank on local news hawking water filters. In between these broadcasts, at least two awful things happen. First, Charlie and Mac attempt to protect a school using firearms and end up profiling people of color. Later, Dennis and Sweet Dee get swindled out of $1,500 by the man who sold them crack in an attempt to purchase a gun to prove guns shouldn't be on the streets. Everyone has made everything worse and Frank has gotten rich by shelling a cause he doesn't believe in.
It's uncomfortable how topical "Gun Fever Too" still is. The Todd Biermann-helmed episode was released in 2013, nine years before a massacre took place at Robb Elementary School in Uvalde, Texas, and the NRA responded with, well, basically Mac and Charlie's flaw-filled plan from this episode. Gun control is still too hot; there's almost no meaningful legislative change in sight. "Gun Fever Too," then, is the ultimate laugh-to-keep-from-crying tonic.
Make no mistake: sequences like the one where Mac and Charlie debate who would win in a gun or samurai sword battle while Dave Foley's Principal wearily looks on are as hysterical as they are scathing. That's the peak "It's Always Sunny" experience, and the core reason this episode ranks higher than equally funny installments like "The Gang Solves the Gas Crisis" or "The Gang Gets Analyzed."
7. The Gang Buys a Boat (Season 6, Episode 3)
Let's be clear: the implication discussion from "The Gang Buys a Boat" would earn it a spot on this list if the episode surrounding it was trash. It's one of the funniest and most stomach-churning sequences of dialogue ever assembled. Period. Dennis' breakdown of how and why he invested in a boat exists at the precise intersection of hilarious and horrifying, and is the sort of moment you laugh at out of safety.
The myriad of ways that "The Gang Buys a Boat" pivots around this discussion — from Mac's "Is that how you wanted those poor women to feel" to the reversal (and re-reversal) of fortune he and Dennis experiences on a sailor-filled schooner — is proof "It's Always Sunny" is savvy at transcending shock value. Dennis' intentions may not be clear, but the show's creators are. That's what makes "the implication" comedy gold.
The thing is, though, that Mac and Dennis are hardly the narrative highlights of "The Gang Buys a Boat." Charlie and Frank spend the whole episode shrimping, feeling slighted, and collecting items from the water Frank dubs relics from an ancient horse massacre (they're garbage Dee is tossing overboard). Dee, meanwhile, gets into a hilarious dance battle with a Wacky Waving Inflatable Tube Man more recently seen in "Nope." No one person captains "The Gang Buys a Boat" to comedy Valhalla. It's a gorgeous, all-time great team effort. That's the truth, not an implication.
6. Paddy's Pub: Home of the Original Kitten Mittens (Season 5, Episode 8)
Look at the above image. There's no way "Paddy's Pub: Home of the Original Kitten Mittens" wasn't making it onto this list for this alone, placing an angry cat in a set of homemade, poorly fitting footgear. Desperation is the currency of Charlie Day's Charlie and, in this episode, he cashed in with an invention for the ages. Kitten mittens (a joke that was the result of poor hearing and is, in episode context, an attempt to merchandise the gang's struggling bar) epitomizes Charlie's foibles. He is a master of the mundane but a man of thwarted ambition. When he tries to dream big, he crosses over into the realm of deluded and absurd almost instantly.
It is for the good of TV comedy that his visions are made tangible. "Paddy's Pub: Home of the Original Kitten Mittens" is home to the funniest ever "It's Always Sunny" moments and elevated the show's capital and comedic reach in one fell swoop. Its relative lack of ambition is the only thing keeping it out of the show's top five installments. Watch it immediately if you haven't.
5. The Gang Turns Black (Season 12, Episode 1)
In the first 90 seconds of "The Gang Turns Black," Dennis Reynolds waves his hand in front of a sleeping Black man's face to confirm he's unconscious before launching into a monologue that insidiously chides people of color for not realizing their worth and declares that "all lives matter." Shortly after, Dennis and the gang become people of color. "It's Always Sunny" has always tackled hot-button issues and has canonically been set in our modern world, but this episode rips any metaphorically protective gloves off before the title card drops. Accordingly, it pulls zero punches for the next 20 minutes.
Consider how many ways "The Gang Turns Black" could have gone wrong. It could have been rich with the lowest common denominator punchlines. Any theses the episode arrived at could have been self-important messaging. Instead, "The Gang Turns Black" is an incendiary musical with incredible visual gags that stick its comedic and emotional landings equally.
The gang break into an ecstatic musical number about going back to "white home" before they suffer any further discrimination at episode's end. Their hysterical panic is the parlance of well-meaning and bigoted white people alike. The gang, like so many sitcom characters before them, will suffer no consequences for this day. (It was a dream, after all.) Those, in the episode's parlance, are the rules. Conversely, to watch the gang is to insulate them from their awfulness, and by implicating the audience, "It's Always Sunny" says more about complicity with white supremacy than any sitcom ever.
4. Charlie Kelly: King of the Rats (Season 6, Episode 10)
The longer it's been on the air, the more "It's Always Sunny In Philadelphia" has weaponized its mundane elements to surprise audiences. Take "Charlie Kelly: King of the Rats." It begins like any other "It's Always Sunny" episode, with a tired Charlie doing "Charlie work." He then monologues about the generations of rats that have died at his hands during "Charlie work" and wonders if life has any meaning. Suddenly, the gang is questioning their cynicism and pivoting toward giving Charlie a day that makes him feel special.
Make no mistake: "Charlie Kelly: King of the Rats" is "It's Always Sunny" at its most moving and genuine. Some might see it as a deviation from the show's bleak and often savage satire. I would call it a rearrangement of priorities. What's brilliant about this episode is that it moves the love which is the undercurrent of "It's Always Sunny" to the forefront.
For the show to make sense at all, the gang must have actual affection for each other. Here, we see it vulnerably, even if it takes the form of a crazy dream sculpture or a spa visit culled from almost thrown-away tickets. In "Charlie Kelly: King of the Rats," even a thankless man can have a wonderful life. If this episode never exists, Charlie is just an "It's Always Sunny" punchline. Because it does, it's a gift to Charlie and television proper. That makes it one of the show's five best installments.
3. The Nightman Cometh (Season 4, Episode 13)
It's no mistake that the top three episodes of this list represent "It's Always Sunny" at its most creatively daring. The long-running show has rarely been shy about taking risks. All the same, "The Nightman Cometh" was a massive gamble when it aired in 2008. The gang committed, with almost no irony, to a fully-realized musical. It was so successful that live versions of "The Nightman Cometh" followed. There's zero question that the episode was a hit with fans, and the way it elevated the show alone makes it top-five worthy. But does "The Nightman Cometh" hold up? Absolutely.
The show has done a superlative job of evolving Mac from a toxically closeted braggart to an out and proud bro. It has almost done wonderful work self-actualizing Charlie. Charlie, it turns out, is the best version of himself as a leader. In "The Nightman Cometh," he steps up to make an entire stage show possible.
Yes, the musical is a ploy to woo the Waitress into matrimony and contains a plot that should land the whole gang on some sort of watch list (I won't write the details here because I don't want to be on said watch list), and that's what makes this an "It's Always Sunny" episode. That doesn't change the fact that it's full of insanely memorable music that finds the beating heart of a broken but striving man. The Nightman cometh to give comedy riches. He does indeed.
2. Mac Finds His Pride (Season 13, Episode 10)
"Mac Finds His Pride" is the ultimate argument for giving a show and its characters the time and chance to evolve. For years, Mac's denied homosexuality was a punchline. At times, it was cheap. "Mac Finds His Pride," the 10th episode of the 13th season, reframes every single Mac gag ever. For most of the episode's runtime, it looks as if the show is going to lean into its worst impulses (the A-plot involves Frank goading Mac to be a token gay guy on Paddy's Pride float). The pivot is a whole other matter. The episode's third act is comparable to "Magnolia," "Little Miss Sunshine," and "Dirty Dancing" in equal measure.
To be 100% clear: it is not a parody of these films. It achieves a catharsis similar to movies that genuinely want to be cinema or offer their characters massive breakthroughs through the realm of physical movement. "It's Always Sunny" has always been a pretty ambitious comedy, but here it becomes a dazzling work of ambitious art, full-stop. Danny DeVito and Rob McElhenney have never been better. The dance is one of the strongest sequences the show has ever filmed. It's fitting that a show with such rapid-fire dialogue uses a scene without speech to truly shift the emotional landscape of a character who could've remained a stock one forever. That's true creative evolution.
1. Charlie Work (Season 10, Episode 4)
If the first 24 entries of this list haven't made it clear, "It's Always Sunny in Philadelphia" is a daring show. And part of what makes it daring and glorious is how surprising and low-key it can be simultaneously. "Charlie Work" is the ultimate example of this. It is an episode with an entire third-act homage to Alejandro González Iñárritu's "Birdman or (The Unexpected Virtue of Ignorance)" which might be one of the funniest scenes ever committed to television, and it is all in service of passing a health inspection. "Charlie Work" is the ultimate high-brow and low-brow crossroads. That is an intersection "It's Always Sunny" thrives at, maybe more than any other live-action, half-hour comedy in existence.
"Charlie Work" begins at that intersection and never leaves it. The episode, expertly directed by future "WandaVision" helmer Matt Shakman, begins with an extended one-shot reveal of live chickens and ends with an extended one-shot that permanently establishes Charlie's next-level restaurant management. (Rewatching the episode recently, the installment reminded me as much of Hulu's "The Bear" as a situational comedy.)
Most importantly, "Charlie Work" feels like everything that makes the show great in microcosm. "It's Always Sunny" began with a grubby setting and shifty characters and built a massive comic universe from both. It's only fitting that the show's best episode contains a massive technical undertaking to Paddy's Pub alone. In "It's Always Sunny," anything is possible in the most unlikely of places. That's truest in "Charlie Work."