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It's Always Sunny Funniest Moments Ranked

3:11 p.m. On a Thursday. The Gang Sets a TV Record. That was around the time "It's Always Sunny in Philadelphia" was renewed for seasons 15-18. This announcement made it the longest-running live-action TV comedy of all time.

How did we make it this far? This is a show full of jokes that would be considered offensive even in the '90s, to say nothing of today's culture. The series follows arguably five of the worst human beings in the history of television on a surreal slice-of-life show that takes place mostly in their Philly dive bar.

Maybe the draw is the obvious chemistry between the "Always Sunny" cast. Maybe it's that the episodes about nothing are all thinly-veiled parables on issues affecting the real world. Or maybe it's simply that nearly every episode has at least one laugh-out-loud, "I can't believe they got away with that" moment. These facts made it extremely challenging to come up with a "funniest moments" ranking. But just like the Gang, we won't back down from a challenge just because it might be impossible, or because we might be wrong, and certainly not because it'll make plenty of people angry. So here we go.

14. Charlie dreams himself into Up

Some "It's Always Sunny in Philadelphia" ("IASIP") episodes take place over several days or a week. Some take place over one day. And some, like Season 9 Episode 6, "The Gang Saves the Day," take place over just a couple minutes when the Gang is stuck in a convenience store during a robbery.

As the situation unfolds, each character has a fantasy about how they handle the situation based on their personality. Mac uses his karate to beat the robber, and then a clan of ninjas. Dennis gets shot in the head, survives, and falls in love with his well-endowed nurse, who loves him back before she herself dies prematurely. Frank eats endless hot dogs. Dee kills the rest of the Gang and frames the robber, a female. Finally, Charlie has his vision.

In it, he's a cartoon, and he and The Waitress fall in love following the robbery. And have kids. And grandkids. And she dies. And cartoon Charlie lets out a bunch of balloons until his house rises up into the sky. That's right, Charlie dreams that his life becomes Pixar's "Up."

13. 'We're keeping the gun, right?'

In many hit, long-running shows, the first season bears little resemblance to what the show becomes. Some fans will tell you that "IASIP" doesn't really start until Danny DeVito's Frank Reynolds arrives in Season 2. But Season 1 has plenty of funny moments, obviously, or there never would've been a Season 2. Such a moment comes in Episode 5, a meditation on gun ownership and violence entitled "Gun Fever" that spawned its own sequel episodes.

In this one, the bar gets robbed, prompting the Gang to get into an argument over whether or not they should own a gun. Dennis and Mac want one, but Charlie and Dee don't. Soon everybody begins to enjoy the power of gun ownership until at the end, Charlie gets shot.

While the Gang visits Charlie in the hospital, Dee says this is conclusive proof that they need to get rid of the firearm. Everybody agrees. But when she walks out of the room, Charlie says, "We're keeping the gun, right?" Mac and Dennis answer in the absolute affirmative, with Dennis pulling the gun out of the back of his pants to show that he will never get rid of it. This is the kind of "we learn no lessons" dynamic that makes the Gang so likable in spite of their unsympathetic personalities. It also lays down one basic rule that has never changed: The boys will never accept Dee or her ideas.

12. Charlie tries to help Frank by throwing up blood on a date

Frank appears in the series when his wife, Dee and Dennis' mother, divorces him. He starts off as the depraved father to the twins, but eventually becomes a father to everybody (even, possibly biologically, to Charlie). But mostly, he's on the hunt for women.

In Season 7 Episode 1, "Frank's Pretty Woman," Frank decides to marry a sex worker. Charlie tries to set up Frank with a woman who will like Frank for his personality instead. The scheme? Charlie pretends to be rich, taking the woman out on the town with Frank posing as his driver. Then Charlie gets sick, leaving Frank to take over and woo her. Charlie starts feeling sick in the limo, all according to plan. Then he projectile vomits enough fake blood to make Dario Argento proud, all of it covering his poor date. Through all the insanity, Frank has been trying to make small talk, and even offers her an egg in her trying time. It doesn't help: The woman takes off into the night and Charlie admits he might have eaten (yes, eaten) too many blood capsules. 

Frank's response to the fail? "I love eggs, Charlie. And I love crabs. And I love boiling denim and bangin' w***es and I don't care if anybody doesn't like that about me, they don't have to stick around."

11. Kitten Mittens

Season 5 Episode 8 opens with one of the most absurd commercials anybody has ever seen: We see Charlie pontificating on how loud cats are (with thunderous, poorly-edited stomping sound effects to make his point) and how buying kitten mittens for them will help keep them quiet, complete with footage of a cat struggling to walk with hand-sewn mittens on its paws.

The rest of the Gang thinks this idea is absurd, but it also leads them to come up with their own ideas for Paddy's Pub products, debating merchandising rights among themselves and stalking The Attorney to orchestrate their deals. In the end, after Kitten Mittens is the only idea that sells, it turns out that The Attorney has tricked them all and gotten them to sign away their rights to everything, including Charlie's absurd creation. But they do stake their claim to the O.G. idea in a way: The episode is called "Paddy's Pub: Home of the Original Kitten Mittens."

10. Charlie goes Reservoir Dogs on a leprechaun

Many of Charlie's greatest moments involve him consuming paint. He writes the theme from "The Nightman Cometh" while huffing off a can of spray paint. In another musical moment, just as the Gang is about to win recognition for their bar, he shows up with silver paint on his nose, singing a morose song about spiders.

But one of the funniest moments in the show, hilarious mostly thanks to the disturbing fright that oozes through the screen, is the ending of Season 11 Episode 8, "Charlie Catches a Leprechaun." In honor of St. Patrick's Day, Charlie has been drinking green paint all day. He also sets a leprechaun snare every year on the holiday, and this time, Charlie finds a little person dressed like a leprechaun in the glue trap.

By the end, Charlie's dancing to "Stuck in the Middle with You" in the basement while the little person is tied to a chair. Charlie pulls out a knife, telling the man he's going to find out if he bleeds green. This sendup of the memorable torture scene from "Reservoir Dogs" is just one of many fantastic movie references in the series. It's sheer, horrific comedy gold, even up to when the Gang finds Charlie and confronts him for his paint-drinking and kidnapping.

The cherry on top? Once untied, the leprechaun disappears as if by magic.

9. Dee becomes a bird in a Gang flashback

The first mention of one of the most iconic "IASIP" insults is a comparison of Dee to the athlete Larry Bird, after which they begin calling her a large, flightless bird at every opportunity. Soon, it becomes the Gang's go-to insult. Nowhere is this joke better delivered, though, than in Mac's flashback to Halloween night in Season 6 Episode 7, "Who Got Dee Pregnant?"

The episode opens with Dee's revelation that she's pregnant and her claim that one of the Gang is the father. After lighting that wick and walking off, she leaves the boys to spend the episode trying to piece that hazy, booze-filled night back together — Mac "invents" the term "brown out" to describe his faded memories of the evening. And Dee becomes a bird.

In the flashbacks, Dee starts out in a dress the Gang says makes her look birdlike. As the flashbacks continue, Dee gets a few yellow feathers on her dress. Slowly, she accumulates more feathers, and even a beak. Finally, in Mac's flashback, he's in the bathroom and, to his recollection, Dee comes in to talk to him — but when we see her, she's an ostrich. Like, a full-sized ostrich, speaking only in squawks. The fact that in Mac's actual memory, Dee is a squawking, strutting, flightless fowl, blows every other "Dee is a bird" joke out of the water.

8. A sordid reunion dance

The high school reunion episode is a truly revelatory look into the history of the Gang. Their high school years were full of rejection and shame. Even Dennis, apparently, was not the golden god he's claimed to be. Dee's friend in rejection, formerly known as Fatty Magoo to Dee's Aluminum Monster, has become very attractive, and now even she isn't on Dee's side — Dee's jealousy over her glow-up has ruined their friendship.

The Gang (including Frank, who naturally tagged along) feels just as dejected as ever — until they decide to save the night. Charlie breaks up the reunion with a monologue about how kids are again using dance as a way to fix their problems à la "High School Musical." He blares "Freedom! '90" by George Michael and the Gang puts on a killer dance scene, winning over the crowd at the apparent conclusion of Season 7 Episode 13, "The High School Reunion, Part 2: The Gang's Revenge."

Then we return to reality. We see these five losers, sweaty and drunk, dancing poorly while everybody looks on with expressions of something between shock and disgust. An after-party is announced — with the Gang disinvited. Epic, sweaty, drunken fail.

7. The birth of Frank -- from a couch

In "A Very Sunny Christmas," the Season 6 finale, the Gang digs into their Christmases Past. The driving story revolves around Dee and Dennis trying to get back at their father, Frank, for always giving himself the gifts he knew his kids wanted. To do this, they stage a twisted version of "A Christmas Carol." For Christmas Present, Dee and Dennis take Frank to his former office's current Christmas party and tell him to hide somewhere so he can hear his former colleagues discussing their distaste for him. Frank suggests they sew him into the office's elegant black leather couch since it's what he always does at home.

Dennis and Dee talk to two employees during the party within earshot of the couch. When one asks if there's a man in the couch, they say no, continually bringing the conversation back to Frank Reynolds until finally they lose patience, insisting one of the people say, "Frank Reynolds is an a**hole." Just as the employee yells those words, Frank is born. Digging his way through a seam, a naked and sweaty Frank emerges in the middle of a holiday party suddenly gone wrong.

He gasps that the leather was too hot and he couldn't breathe. The last we see of him is his naked butt as he lumbers down the hall.

6. Charlie's Pepe Silvia conspiracy

One could say a TV moment becomes legendary when it gets turned into a popular meme. By that metric and many others, Charlie's Pepe Silvia conspiracy scene is truly legendary.

In Season 4 Episode 10, "Sweet Dee Has a Heart Attack," Charlie and Mac get jobs in a corporate mailroom in order to get health insurance. But the burden of button-down responsibility is too much for the two — especially for Charlie. The amount of mail coming in overwhelms the man whose work normally consists of killing rats and cleaning up bodily fluids. Charlie goes mad, and the revelation is absolutely brilliant.

Mac, after getting caught sneaking into a corner office, comes down to get Charlie only to find that the mailroom looks like something out of a true crime episode. Charlie has taped correspondences to the wall with lines of string running from paper to paper, all centered around one recipient: Pepe Silvia. Charlie insists there's no Pepe Silvia, and when he went to talk to Carol in HR, he discovered there's nobody in HR — it's an entirely fake company.

"There is no Pepe Silvia," Charlie sputters while sucking down a cigarette. And how does Charlie find out Pepe Silvia doesn't exist? From Barney, of course. Barney is Charlie's hallucination of a man in a black hat and trench coat who tips him off to the conspiracy.

5. Frank talking to the psychiatrist

The Gang may be the most dysfunctional bunch of scallywags ever to grace a TV screen. And in Season 8 Episode 5, "The Gang Gets Analyzed," we get our first glimpse of just how deep their demented rabbit holes go. Each group member's individual therapy session is a hilarious and horrible exploration of their inner pathologies. But really the funniest is Frank's.

Frank starts off not wanting to open up to the psychiatrist. He says he did that once and ended up in a mental institution, though it was also designated for people with physical deformities. This was where he met his first love, who was always smiling — she had no lips, "but her mouth was still very much in play." After recalling how the girl died two weeks later, he starts screaming, "You unzipped me, Doc," following it up with a tear-soaked, "I hate you!" His complete mental collapse and reversion to that moment in his past is absolutely ridiculous and all too memorable.

4. Royal McPoyle, Pocono swallow

Many fans would tell you that Seasons 3-7 are the golden heart of "It's Always Sunny In Philadelphia," but the later seasons deliver laughs any sitcom would be proud of at its high point. Season 11 Episode 7, "McPoyle vs. Ponderosa: Trial of the Century" is an absolutely hilarious sendup of courtroom dramas. As an aside, this episode features some amazing cameos, from Reginald VelJohnson (of "Family Matters, "Die Hard," and "Crocodile Dundee'" fame) as the judge to acclaimed filmmaker Guillermo del Toro as Pappy McPoyle.

The trial culminates in Charlie cross-examining Pappy about birds, showing a truly inspiring bit of knowledge about the one on the McPoyle family crest: the Pocono swallow. As this brilliant legal(ish) monologue escalates, Charlie takes Pappy's hat off, introducing the court to Royal McPoyle, the family bird hiding there. Royal has a history of attacking the McPoyles. Charlie tells a bird expert to talk to the bird and ask him about it, and when the expert says he can't, the courtroom erupts. Dennis' ex-wife chases a laser pointer like a cat, the judge bangs his gavel, and Pappy sends Royal to attack The Attorney (who's representing the McPoyles) — another instance in which the Gang continues to ruin this lawyer's life.

The madness of that final monologue and that zoo of a climactic scene is zany comedy at its greatest.

3. Frank's intervention

Here's another Frank-centered moment, because once Frank joins the show, he has a killer moment in just about every episode. Season 5 Episode 4, "The Gang Gives Frank an Intervention," centers on Frank's descent into depravity: The rest of the Gang stages an intervention for him, and it's the worst, most over-the-top intervention ever captured on TV.

Frank walks into the bar, where they're staging the intervention, and Charlie, Dennis, and Dee circle him while pointing, making noise, and screaming, "Intervention!" before sitting him down and telling him he's caught. When they say they're going to tell him how he's an a**hole, Frank thinks he's walked into a roast. The scene is lifted even more over the top by the fact that the Gang is drunk, Frank enters with a gun pulled, and whenever anybody gets off track, everybody says "Intervention," as a way to steer the conversation back in the right direction. When Mac shows up with Gail the Snail, they all take turns (mis)using the term to "intervene on" the Snail being at their bar and kick her out. It's amazing.

Most importantly, this episode may have also invented the current real-world trend of drinking wine out of a can. At least, that's what we'll choose to believe.

2. Dennis explaining the DENNIS system

Every character has evolved into a larger-than-life version of themselves over the many seasons of "It's Always Sunny in Philadelphia." Dennis morphed from vain ladies man to sexual predator (look up "the implication"). This escalation can arguably be traced to the moment where his calculated approach to courtship became public: Dennis' explanation of his art of seduction in the eponymous episode "The D.E.N.N.I.S. System."

In Season 5 Episode 10, Dennis attempts to tutor the Gang on how to get any woman's undying devotion. It proves ineffective, and also leads to the discovery that Mac and Frank have their own systems for picking up the women Dennis rejects ("I got my magnum condoms and a wad of hundreds; I'm ready to plow," says Frank). The step-by-step how-to is a disturbingly accurate description for how scumbag men sometimes attract women, and it makes a perfect acrostic with Dennis' name.

As Dennis walks the Gang through these steps on an easel pad, his in-depth explanation of how he played with the poor woman at the center of the episode (played by Jill Latiano, real-life wife to Dennis' Glenn Howerton) is nothing short of brilliant and horribly politically incorrect.

1. Frank hijacks a boat and rambles about his life

"IASIP" isn't just a brilliant show: It's home to a brilliant movie-within-a-show called "Thunder Gun Express." This movie is the namesake for Season 7 Episode 11, and the Gang will stop at nothing to see it. But there's traffic (thanks to Obama, they lament), so they go their separate ways to make the showtime. Dennis stays in his car. Dee, Mac, and Charlie get on a trolley, and eventually Charlie and Dee take to the sewers. Meanwhile, Frank hijacks a Philly tour boat full of Chinese tourists.

Expected to actually give a tour, he introduces them to Philly as only Frank Reynolds could, telling them the Schuylkill River is full of strange creatures and the bodies of unsolved murders. Then he starts talking about the Gang's most memorable moments, his adventures with Charlie (including pooping the bed and blaming it on him), and as always, his quest for women — made even funnier when the translator explains to the tour group that Frank has sex with a lot of sex workers.

The episode ends with Frank in police custody. "Thunder Gun Express" is in many ways the perfect centerpiece for the series. And while this moment may not be the most over-the-top comedic explosion, the scenario in which Frank narrates his antics and those of the Gang to a group of Chinese tourists is a steady comedic slow burn that gets funnier with every watch.

Kind of like "It's Always Sunny in Philadelphia" itself.