It’s Always Sunny In Philadelphia is a show with a simple premise that’s sprawled over its double-digit seasons to address, well, pretty much everything. How a comedy about five Philadelphia bar urchins who are truly terrible people can be this nuanced — and this funny — really is astounding. But why Always Sunny has prevailed is really pretty simple: the characters live in a universe all their own, and the writing has fleshed The Gang out to make them each uniquely terrible.
There are so many great episodes over the show’s 13 seasons and counting that it’s tough to really narrow down the very best ones. They all have specific moments that make you laugh out loud, and whether you’re a fan of the subtle changes in Mac’s sexual awakening or watching Dennis slowly become unhinged, there’s always something in an episode that makes it worth the watch.
Still, decisions must be made here. And we’re counting down the 10 very best episodes of It’s Always Sunny In Philadelphia, which means some tough but fair choices. And to be clear, there are far too many great episodes of It’s Always Sunny in Philadelphia to include on this list. It could be twice, or maybe three times, as long and we’re almost certainly going to miss some good ones. But these are the 10 best according to an extremely biased and unreliable narrator that’s flawed but, ultimately, lovable. Maybe.
10) The Gang Hits The Road (Season 5, Episode 2)
The Story: Charlie’s never left Philadelphia, and he wants to take a road trip to the Grand Canyon.
Why It’s On The List: The show had never really left the bar or Philly proper, and this is it’s big chance to expand its horizons with Charlie leading the way. They don’t get far. Distracted by Charlie admitting that he’s also never eaten a pear, they go to a market to knock that off his bucket list. And then they try to travel in a U-Haul filled with stuff they got at the market. There’s haggling, a fire and a lot of car shuffling. There’s also an extremely disgusting lesson in air physics in here, but once you see Sweet Dee sing “Runaway Train” to a teen while filling a pee jar, you’ll forget all about ever trying to get to the Grand Canyon.
9) The Gang Broke Dee (Season 9, Episode 1)
The Story: The Gang’s abuse of Dee has finally broken her. Dennis wants to set her up with a man with equally low self-esteem, but the rest of The Gang has plans for Dee’s comedy career.
Why It’s On The List: This just might be the quintessential Dee episode of Sunny. At first it’s easy to feel bad for Dee’s plight, but greed eventually takes over as her meteoric comedic rise propels her to what she believes will be the big time. It’s a hilarious crash landing of an episode, and maybe some of the greatest lengths The Gang has taken to pull off a scam. Of course, it’s on one of its own.
8) The D.E.N.N.I.S System
The Story: Dennis reveals to The Gang the ways in which he seduces women. It’s exactly as creepy as it sounds.
Why It’s On The List: Dennis is a sociopath, and this might be the first time we see the extent of how broken his relationships are. These tendencies, unsurprisingly, are further exacerbated and elaborated upon in later episodes. But watching him explain the acronym in the bar, and the reaction it gets, is an amazing moment on the show. We get to watch The Gang mangle his apparently perfect system, frustrating Dennis as he also fails to re-D.E.N.N.I.S a woman who had fallen in love with him. No matter how you feel about Dennis manipulating women, you’ll always remember Frank accidentally letting “massive condom for my magnum dong” fall out of his wallet at the fair.
7) The World Series Defense (Season 5, Episode 6)
The Story: The Philadelphia Phillies won the World Series, and the gang is in court explaining what happened the night they won the pennant.
Why It’s On The List: Charlie’s rant against Major League Baseball and the Phillies’ mascot at the end of the episode is enough to get on the list here, but there’s a lot going on here. Mac’s love letter to Chase Utley is a memorable moment that’s had real-life implications, and it made anyone who watched the episode want to try riot punch. Charlie’s mascot antics and the gang’s quest to get into the game despite tickets is a cruel irony because, sadly, they had tickets. The episode is only made funnier by The Gang’s slight mispronunciation of certain words to avoid copyright infringement. This isn’t the only episode that’s explored a baseball urban legend, but it’s one of the best examples of a show taking a major sporting moment in its city and making it their own.
6) The Gang Gives Frank An Intervention (Season 5, Episode 4)
The Story: Frank has gone a bit too far off the rails, even for The Gang, who stages an intervention.
Why It’s On The List: This might surprise you, but The Gang does not know how to stage a proper intervention. Watching them struggle to find someone willing to stage the kind of ambush they want is great, as is watching Frank drink to excess and be gross. This episode also introduces the world to wine in a can, which is a real thing now. As is, at least in Charlie’s mind, the game nightcrawlers. It’s good to air grievances sometimes, you learn a lot.
5. The Gang Goes To A Water Park (Season 12, Episode 2)
The Story: The Gang splits up and has their own day of fun at the water park. Mac and Dee get stuck in a water slide too small for adults, Dennis finds a protege to teach his grifting ways and Charlie and Frank find a loophole to cut lines and get onto every ride in the park in a day.
Why It’s On The List: Mac and Dee mess up immediately, but things actually go pretty well for the rest of the gang until it all falls apart at the end. Dennis tries the Matchstick Men thing with a young girl who pulls a scam on him, and it goes well for a while! It was weird to root for him to bond with a street urchin, and for Charlie and Frank to have fun despite the latter shouting “AIDS” over and over again. There’s something really funny about Dee and Mac trapped in a water slide the entire episode as children pile up behind them, and the hilarious payoff at the end is immensely satisfying. One fun note about this episode: the lifeguards are Game of Thrones showrunners David Benioff and D.B. Weiss. No wonder things went so off the rails.
4) Chardee MacDennis: The Game of Games (Season 7, Episode 7)
The Story: The Gang gets bored and decides to play Chardee MacDennis, showing it to Frank for the first time. It’s revealed Charlie and Mac have never won the game, and Frank joins their team to play Dennis and Dee.
Why It’s On The List: Here are the games Chardee MacDennis is based on: Mousetrap, Chutes and Ladders, Sorry, Boggle, Wheel of Fortune, Risk and a bunch of other stuff. But better! We learn all this later in Chardee MacDennis 2: Electric Boogaloo. But the first time we learn about the drinking game they conceive it’s completely and totally insane, and of course it’s very real. The episode is complete chaos, but perhaps the highlight is Frank, trapped in a dog cage, asking to be put up on the bar so he could see what The Gang’s up to. You’ll, uh, get it when you see it.
3) The Gang Beats Boggs (Season 10, Episode 1)
The Story: The Gang tests the limits of commercial air travel in attempting to “beat” Baseball Hall of Famer Wade Boggs, who according to legend once drank 70 (or more!) beers on a single cross-country flight the night before a game. Four members of The Gang go for the record, while Mac acts as “commissioner” and keeps the game going, to mixed effect.
Why It’s On The List: This episode is completely insane and breaks so many TSA rules that basically everyone involved should be in prison forever, but it’s the perfect recipe for a memorable and hilarious episode of Sunny. Frank and Dennis get distracted trying to join the Mile High Club, Dee burns out hot and bright and Charlie is visited by the “ghost” of Wade Boggs, who isn’t dead at all and actually says it was 107 beers. But Sunny is not a show about realism, it’s about five criminally broken people making the worst decisions possible for our entertainment. And secret hatches in commercial jets that let you go anywhere in the plane.
2) Charlie Work (Season 10, Episode 4)
The Story: The Gang tries to do a “chicken and airline miles scam” while Charlie tries to prepare Paddy’s for a surprise health inspection. In the process, we learn just how much work Charlie does to keep the bar afloat.
Why It’s On The List: A Charlie appreciation episode is extremely warranted, and it shows a side of The Gang that we often don’t see. Perhaps the most meme-able image from It’s Always Sunny is the picture of Charlie breaking down a government conspiracy, with Pepe Silva scrawled on a bunch of papers behind him. But this is Charlie actually pulling the strings, manipulating a health inspector, and finishing the gang’s half-baked scam for them while moving everyone in Paddy’s around like chess pieces on a surprisingly clean board.
That The Gang doesn’t notice all the work Charlie puts in to keep things afloat is fitting, and it makes the audience think about the unreliable narration of the show. Is Charlie a lot smarter than he seems? Is he the one keeping everything going? At the very least, we learn that he certainly knows how to pull off a chair prank.
1) The Nightman Cometh (Season 4, Episode 13)
The Story: Charlie has written a musical and needs The Gang’s help in pulling it off.
Why It’s On The List: Charlie’s musical genius is briefly touched upon in multiple episodes, but this is the one where we realize he can actually create and pull off a rock opera based loosely on his twisted childhood. This is the first real glimpse into Charlie’s mind, and there’s a lot going on in there. It’s also not the last time he has a scam to pursue The Waitress, but it’s definitely the highlight of his attempts to seduce her.
Watching The Gang’s ambivalence to Charlie’s artistic vision slowly wear on him is amazing, and that he actually pulls off a pretty solid play — though really a comedy — is one of the highlights of the series. Charlie literally descending from above the stage as the sun to pitch The Waitress caps off one of the weirdest community theater performances in TV history.
Dee can’t lower her arms, Mac wants to do karate, and Frank demands a troll toll for the boy’s soul. I think that’s how the song goes, anyway. It’s a classic.
