The messy, eccentric owners of Paddy’s Pub on the sitcom, It’s Always Sunny in Philadelphia, have been entertaining audiences for 16 seasons on FX—and in later seasons, FXX—with their scheming and depravity. The series premiered in 2005 and has run for over 170 episodes so far, making it the longest-running live-action sitcom, and at least two more seasons are on the way, as it has been renewed through Season 18.
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Nothing is below the Gang, and that’s what makes It’s Always Sunny such a great, hilarious show. The series is known for its dark humor and chaotic characters, and there’s almost nothing the Gang hasn’t done. But it also manages to tackle social and political issues with nuance and insight, in addition to humor. It’s Always Sunny is a bold show, willing to go almost anywhere, and that choice pays off. The funniest episodes span the entire series, from fan-favorite classics to over-the-top stories.
10 “The Gang Solves the Gas Crisis”
Season 4, Episode 2
Image via FX
In “The Gang Solves the Gas Crisis,” Mac (Rob McElhenney), Dennis (Glenn Howerton) and Charlie (Charlie Day) developed a scheme to buy gas, stash it in the basement and resell it for a profit a year later but ended up trying to sell it door-to-door, with each assigned a role. Meanwhile, Frank (DannyDeVito) and Dee (Kaitlin Olson) try to frame Bruce Mathis (Stephen Collins) in an attempt to get his inheritance money, and in the process, Frank begins to suspect Dee was plotting to kill him.
“The Gang Solves the Gas Crisis” presented classic It’s Always Sunny schemes which spiraled out of control. They were doomed from the beginning, with hilarious moments every step of the way. But the best part of this episode was Charlie living up to his role as “the wild card,” both in a number of small moments and a literally explosive ending. By the end, it’s revealed he cut the van’s brakes, sending it and Rubbermaid containers full of gas barreling into another car.
9 “Mac and Dennis Break Up”
Season 5, Episode 9
Image via FX
“Mac and Dennis Break Up” was exactly what it sounded like—Mac and Dennis decided they needed to spend some time apart after Dee compared them to an old married couple, leading to Mac going to live with Charlie and Frank, while Dennis went to spend time with Dee. In the end, everyone was annoyed with one or the other of them and set them up to get them back together.
Dee’s observation in “Mac and Dennis Break Up” was apt—Mac and Dennis indeed bickered like an old married couple whose relationship had gone stale, from Mac questioning Dennis about why he wasn’t answering his calls to Dennis choosing to rent a different movie. But some of the funniest moments came from Frank, especially as he cleaned his toenails with a steak knife, cut himself and used garbage to bandage the cut.
8 “The Nightman Cometh”
Season 4, Episode 13
Image via FX
Charlie wrote a musical in the season 4 finale, “The Nightman Cometh,” based on his song “Nightman” and possibly inspired by his own experiences. The Gang were cast in the starring roles, and they all had strong opinions when it came to their characters. Ultimately, Charlie used the show to propose to the Waitress (Mary Elizabeth Ellis), who naturally turned him down and only agreed to see the musical because Charlie promised he’d leave her alone if she did.
“The Nightman Cometh” was a departure from the Gang’s typical antics. The episode is often hailed as one of the best episodes of It’s Always Sunny, thanks to the ridiculous musical. Although the plot and lyrics were disturbing, the way the show actually played out was hilarious, from Frank’s mispronunciation of “boy’s soul” as “boy’s hole” to Dee’s ad-libbing. The episode was also a fitting season finale, because where else can one go from there?
7 “The Gang Gets Quarantined”
Season 9, Episode 7
Image via FX
In “The Gang Gets Quarantined,” the Gang was looking forward to participating in a singing competition in which the winners got to open for Boyz II Men in concert, but as a flu outbreak spread through Philadelphia, they voluntarily quarantined inside Paddy’s to preserve their voices. Dennis decided to order a pizza, but after interacting with the delivery man, the Gang quarantined him separately. In the meantime, Frank became paranoid about getting sick.
The Gang quarantining went about as well as one would expect, with just about everyone breaking their self-imposed rules and things descending into chaos. “The Gang Gets Quarantined” was full of hilarious moments, but the best part of the episode was Frank, as his paranoia deepened and led to increasingly over-the-top behavior. One of the funniest moments came from Frank wearing next to nothing and being slathered in hand sanitizer.
6 “Mac and Dennis Move to the Suburbs”
Season 11, Episode 5
Image via FX
After burning down their rent-controlled apartment and struggling to find a new place, lower rent and more space lured Mac and Dennis to the suburbs in the appropriately titled “Mac & Dennis Move to the Suburbs.” They found a nice house in a quiet cul-de-sac, but Frank was adamant they wouldn’t last. So the three of them bet on it, which didn’t take long for Frank to be proven right, as Mac and Dennis slowly unraveled.
The suburbs are pretty much the last place anyone in the Gang belongs, and “Mac & Dennis Move to the Suburbs” perfectly illustrates why. The episode was part The Shining, part marital drama in a way that only It’s Always Sunny can do. Mac and Dennis’ relationship disintegrated as they became increasingly frustrated with each other and their behavior became more and more unhinged, as they grew hostile towards each other and their neighbors.
5 ‘Mac and Charlie Die’
Season 4, Episode 5
Image via FX
In the two-part “Mac and Charlie Die,” Mac and Charlie tried and failed to frame Mac’s dad, and when he was released on parole, the two feared he’d kill them in retaliation. To protect themselves, they faked their own deaths, with the funeral held, appropriately, at Paddy’s and Dee suspecting they weren’t actually dead. Meanwhile, Frank and Dennis find a glory hole in one of the bathroom stalls at the bar.
“Mac and Charlie Die” presented a wonderfully over-the-top scenario for Mac and Charlie, along with a hilarious side plot for Frank and Dennis. Things went wrong pretty much from the start, as Mac and Charlie planned to stage a car accident and Mac failed to jump out before the crash as planned, followed by a series of failed attempts at destroying the car. Frank and Dennis’ dive into anonymous sex was just as entertaining, if not more so.
4 ‘The Gang Buys a Boat’
Season 6, Episode 3
Image via FX
Mac, Charlie and Dennis used their extra money to buy a boat in the straightforward “The Gang Buys a Boat.” Despite initially disagreeing over what kind of boat to get, they settled on a houseboat called The Drowning Sailor after a salesman showed it to them, largely because their short attention spans kept them from considering other options. Mac and Dennis spent time in the community around boating, while Charlie and Frank planned to go shrimping.
It’s easy to imagine the sorts of chaos the Gang could get into on the open seas – or how things might devolve. “The Gang Buys a Boat” didn’t have much of a plot but rather hinged on the show’s characters, essentially just moving them from the bar to a boat. Each had their own ideas of how to enjoy the boat until it all ended, in true It’s Always Sunny fashion, in a fire.
3 ‘CharDee MacDennis 2: Electric Boogaloo’
Season 11, Episode 1
Image via FX
“CharDee MacDennis 2: Electric Boogaloo” revisited the Gang’s homemade board game, whose title was made up of the names of its creators. Gameplay lasted 15 minutes—not including frequent stoppages—with two teams playing against each other through three stages, each with a separate set of rules. In this Season 11 follow-up to an episode from Season 7, the Gang demonstrated the game for an interested executive, but things quickly went awry.
When just about everything the Gang did was depraved, it was no surprise they came up with their own twisted board game—nor was it a surprise that the game had a convoluted, complicated set of rules and turned into chaos. In “CharDee MacDennis 2: Electric Boogaloo,” the Gang declared a truce in the hopes of winning over the executive, but did such a truce ever really stand a chance?
2 ‘The Gang Goes to Hell’
Season 11, Episode 9
Image via FX
The two-part Season 11 finale, “The Gang Goes to Hell” saw the Gang going on a Christian cruise after Mac won tickets through his church. The episode opens with the Gang apparently in heaven, donning white robes in a white room, with Mac asking to explain what happened, so they can be judged accordingly. Their bad behavior got them locked in the brig, where they were trapped as the ship started to sink. The second part revealed whether the Gang was really dead.
A Christian cruise isn’t a good place for the Gang, and it’s hard – no, impossible – to imagine that, upon their deaths, they’d end up in heaven. Their exploits on the cruise were hilarious enough, but one of the best moments came at the end of Part 2, where the audiences learned the Gang was retelling this story solely to receive financial compensation after their bad experience. But the episode also had its sweet moments, as the Gang acknowledged they cared about each other when faced with what they thought was certain death.
1 ‘McPoyle vs. Ponderosa: The Trial of the Century’
Season 11, Episode 7
Image via FX
In “McPoyle vs. Ponderosa: The Trial of the Century,” Liam McPoyle (Jimmi Simpson) and his family sue Bill Ponderosa (Lance Barber) for spiking the milk with bath salts at the wedding of Liam and Maureen Ponderosa (Catherine Reitman), which led to Liam being attacked and losing an eye. Charlie and his Uncle Jack (Andrew Friedman) represented Bill, and old grievances resurface as a result of the lawsuit. The episode was a follow-up to the Season 8 episode “The Maureen Ponderosa Wedding Massacre.”
“McPoyle vs. Ponderosa: The Trial of the Century” was quintessentially It’s Always Sunny, with a callback to a previous episode, an absurd scenario, and even more absurd character and cameos. Unsurprisingly, the trial was ridiculous, from Jack’s giant fake hands, which he insisted were real, to the McPoyle family’s pet bird with a penchant for violence. Each witness called to the stand was hilarious in their own right. The only normal character present was the judge, leading to one of the best moments in the episode, when he was horrified to learn his next case was also centered around the Gang.
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