The 10 Best Episodes Featuring 5 of the Shittiest People from Philadelphia
It’s hard to believe that we’re more than halfway through the 16th season of It’s Always Sunny in Philadelphia. As of 2021, it has surpassed The Adventures of Ozzie and Harriet as the longest-running live-action American comedy series in television history. These first episodes of the new season are so high-quality that it doesn’t feel like the show has even skipped a beat. From the humblest of roots, three friends turned a TV pilot shot on bottom-bin cameras into one of the most iconic, quotable, and downright funniest sitcoms of the 21st century.
For those who don’t know, the show centers on a group of friends referred to simply as “The Gang,” who own a bar together in South Philadelphia called Paddy’s Pub. Narcissistic sociopath Dennis (Glenn Howerton) and his twin sister Dee (Kaitlin Olson), the latter of whom entertains delusions of grandeur that she is a talented performer, own Paddy’s with the gay hyper-masculine Mac (Rob McElhenney) who is in charge of security, and the sweetly idiotic Charlie (Charlie Day), who serves as the bar’s janitor.
Early in the show’s run, Frank (Danny DeVito), who raised Dennis and Dee but is later proven to not be their biological father, also joins the Gang. He takes a particular liking to Charlie, with whom he decides to live in squalor despite being rich. The Gang frequently gets into misadventures to make money, raise their credibility, or both. Occasionally, these even tie into current events or political controversies, like fights over abortion and guns.
The show is the basis of many popular memes online. Scenes from it frequently make the rounds on video-sharing sites, and quotes from it go viral on aggregation websites. The show has had a bit of a second wind in recent years due to the success of The Always Sunny Podcast, hosted by McElhenney, Howerton, and Day as they go through each episode of the show from the beginning, moderated by show-writer and director Megan Ganz. Live versions of these podcasts have sold out arenas in countries all over the world.
My relationship with the show began over a decade ago when I was a college freshman. In a sentence Gen Z wouldn’t understand, those DVDs made their way through everyone’s dorm room at one point or another, and the show was a cult hit despite relying on physical media. And recently, I’ve started to revisit many of those classic episodes.
To celebrate the show and its newest season, here’s a list of my personal favorite episodes. I hope this inspires those who haven’t checked the show out yet to do so, as well as prompts die-hard fans to compare and contrast their list of favorites with my own. Almost every episode has at least one great or laugh-out-loud moment, so this was a tough selection, but one that I believe reflects everything I love about the show and why it’s worked so well for so long.
“The Gang Goes on Family Fight” (Season 10, Episode 8)
This is a great episode to introduce people to the show. It’s one of the more accessible because of the simplicity of the plot: it’s basically just an episode of Family Feud, but with the Gang participating and all the shenanigans that come along with that. Props to a great turn by Keegan-Michael Key as the game show host.
“A Very Sunny Christmas”
It’s certainly entered my rotation of Christmas-time viewing. The scene where Charlie, sitting on a mall Santa’s lap asking him if he had sex with his mom, is downright unforgettable, as is the revelation of how tragic Charlie and Mac’s respective childhood Christmases were.
“The Gang Tries Desperately to Win an Award” (Season 9, Episode 3)
One of the more meta episodes, as it seems to be commenting on the lack of any serious nominations for the show by the Emmys. Mac, Dennis, and Dee try to figure out how to be more likable. The song Charlie sings at the end is one for the ages.
10. “The Gang Goes to a Water Park” (Season 12, Episode 2)
I really like episodes where the Gang splinters off from one another, and this is one of the best examples. The simple premise of the Gang going to a water park actually allows us to delve into how they respond to what they encounter. Dee and Mac get stuck in a waterslide that keeps sending kids down who smack into the trapped duo, while Charlie and Frank claim that they’re dying in order to skip lines.
Dennis has the most intriguing arc as he pairs up with a girl named Abby (Jayden Bartels) in order to con people in a take-off on Paper Moon. I see great potential in Bartels because acting alongside one of the funniest casts in TV history can’t be easy, especially for a younger actor, but she really nails the role. This episode is a fun one to revisit, and I hope you watch it with as much glee as Mac has on his face in the last frames of the episode.
Funniest line: “If you were born in China, you would be the head of some factory by now…or they would’ve thrown you in the river because you weren’t a boy.”
9. “The Gang Goes to the Jersey Shore” (Season 7, Episode 2)
Another story where there are three separate pairings of characters, this episode is just downright fun. Dennis and Dee’s nostalgia for their time on the Jersey Shore as kids lead the Gang to depart for the beach. Mac and Frank get drunk off “rum ham” and float off to sea, only to be picked up by a party boat. Charlie gets to spend an unforgettable night with his beloved Waitress, played by Charlie Day’s real-life wife Mary Elizabeth Ellis. Dee and Dennis get caught up in the seedy underbelly of the Shore, end up having the worst experience, and vow to never come back. This is also the first of two entries on this list from the “Fat Mac” season, where Rob McElhenny gained 60 pounds between seasons. Every great sitcom has a beach episode, and Sunny’s also happens to be one of its best!
Favorite scene: A montage of what everyone in the Gang is up to set to “Vacation” by the Go-Go’s. It ranges from the celebratory to the very violent, and yes, it even includes more rum ham.
8. “The Gang Cracks the Liberty Bell” (Season 4, Episode 11)
When a non-native thinks of the city of Philadelphia, you either think of sports movies like Rocky or Silver Linings Playbook, or its ties to the nation’s early history. This episode is somewhat divisive, but I get a kick out of it, maybe due to my interest in the American Revolution. Dennis, Charlie, and Mac want to get Paddy’s Pub designated as a historic landmark, and thus, spin a yarn about their counterparts in 1776. The episode lets you know its irreverent intentions from the get-go, with an intro featuring the Gang commenting on how ugly they think George Washington was. Charlie and Frank sell fur pelts and consort with local Native Americans. Perpetually down-on-his-luck priest-turned-bum Rickety Cricket (David Hornsby) is here reimagined as a colonel in the British army who falls in love with Dee, who turns out to be a witch. If all that isn’t enough to sell you on this fantastic episode, I don’t know what is.
Favorite moment: Dennis and Mac in disguise as British aristocracy practicing over-enunciating “Yeeesssss….” proves a timeless bit can involve repeating just one word.
7. “Charlie Work” (Season 10, Episode 4)
The first of two day-in-the-life episodes on this list, “Charlie Work,” as its title would imply, focuses on Charlie trying to wrangle the Gang during a surprise health inspection at the bar. The Gang has gotten involved in a scheme involving chickens, airline miles, and thousands of steaks that arrive, all coinciding with the inspection performed by someone Charlie’s never met before. The third act is one continuous shot and has a drum-heavy score, which made people believe it was inspired by the then-recent Birdman, but the episode had been written and filmed before Birdman was on anyone’s radar. I love a good Charlie episode (there’s at least one more coming up on this list) and this one stands out as a particular treat.
Favorite moment: Charlie losing it at Dee, cursing her while walking away only to immediately transition back into service mode for a customer.
6. “Being Frank” (Season 11, Episode 6)
This episode is pretty unique in the show’s output, in that it’s a day in the life entirely told from the perspective of only one member of the Gang, Frank. He’s utterly oblivious to the Gang’s latest scheme but is forced to go along with it. Along the way, he gets a second wind after doing all the drugs in a drug closet, disrupts a family sitting shiva, and we get to hear his innermost thoughts. We are also given a glimpse of what it’s like when Frank and Charlie play their oft-teased “Night Crawlers” game. This a perfect example of a great Frank-centric episode.
Funniest line: Frank’s innermost thoughts on Mac are “Oh God, this one creeps me out, I hate being alone with him. If he touches me, I swear to God, I’m gonna freak out!”
5. “The Gang Beats Boggs” (Season 10, Episode 1)
Inspired by an urban legend that baseball great Wade Boggs drank at least 50 beers on a cross-continental flight, the Gang tries to emulate his example and see who can drink the most on a flight to California. There’s even confusion as to who inspired this whole odyssey, as Charlie believes Wade Boggs is dead (he isn’t) and Dee keeps thinking he’s Boss Hogg from The Dukes of Hazzard. The contest continues in the midst of Dennis trying to score with a woman he admits he thought was “Great Plains trash,” but was just “desert trash” based on her multiple gecko tattoos. There’s at least one more entry on this list to feature a competition, but sometime this simplest of storytelling tricks can yield the greatest of results.
Favorite scene: The ending of a very drunken Charlie hitting a home run in California is among the happiest in the show’s history.
4. “Flowers for Charlie” (Season 9, Episode 8)
Game of Thrones showrunners D.B. Weiss and David Benioff wrote this take-off on the classic Flowers for Algernon in which Charlie takes a pill that he’s told will make him smarter. Sure enough, Charlie is seemingly picking up new skills and interests, while Dee, Dennis, and Mac seem to downgrade into even deeper stupidity in his absence. The twist at the end is what makes this episode for me, and it only goes to show that Charlie cannot be quashed or restrained from being his true, authentic self.
Funniest line: “Stupid science bitch couldn’t even make I more smarter!”
3. “Who Pooped the Bed?” (Season 4, Episode 7)
It takes a certain amount of talent to be able to pull off potty humor effectively. South Park does it, but not many other shows would risk spending an episode talking about a literal turd. Not only did Sunny take this chance, but it also turned out to be one of the show’s best episodes. Charlie and Frank share a bed together, and they need to solve the mystery of which one of them keeps defecating in it. When a second turd emerges when Mac and Dennis also sleep in the bed, the mystery only deepens. Dee freaks out in an art gallery when all she can see is poop. Her friend Artemis (Artemis Pebdani) gives a forensic breakdown of how the poop came to be in a final monologue that is one of the show’s best. Why? The episode’s thesis is said by Frank at the end: “Because poop is funny!”
Favorite scene: When a scientist is examining the turd, finding bits of newspaper, credit card, and wolf hair, only to be told by both Charlie and Frank that’s “inconclusive.”
2. “Chardee MacDennis: The Game of Games” (Season 7, Episode 7)
Bored while at the bar one day, the Gang decides to play a game they invented entitled Chardee MacDennis which takes elements of famous board games through their warped, perverted perspective. Dee and Dennis face off against Charlie and Mac, who have never won. Frank has never played before, and he’s constantly playing catch-up to the game’s strange rules and challenges. As much fun as it is to watch the Gang collaborate, it’s even better to see them compete, and this episode is a perfect embodiment as to why. I can’t sum up any better why this episode is so effective than YouTuber Captain Midnight.
Funniest line: “BECAUSE DENNIS IS A BASTARD MAN!”
And #1, “The Nightman Cometh” (Season 4, Episode 13)
Occasionally, an episode comes around that redefines the show’s potential, and becomes a milestone in its run. We can all probably name an episode like that for our favorite shows, but in terms of It’s Always Sunny, I think that episode is clearly “The Nightman Cometh.” A rare musical episode for the show, its focus is the titular musical that Charlie has written.
The Gang decides to stage it and cast themselves in various roles. During the stage performance, Dee plays a princess; Dennis plays little boy-turned-heroic Dayman; Mac, sporting cat eyes, plays the feared Nightman; and Frank plays a devious troll. Charlie becomes a power-mad director, and the whole thing is revealed to have been conceived by him as a way to win the affection of the Waitress, who ultimately rejects his advances as always. The episode was so popular, a multi-city tour of a staged production of it with the cast reprising their roles occurred in 2009. This is the pinnacle of It’s Always Sunny for me personally, an episode that I love to revisit, laughing hard every time I watch it.
Favorite song: “You gotta pay the troll toll…”