10 Most Entertaining ‘It’s Always Sunny in Philadelphia’ Episodes, Ranked

It’s Always Sunny In Philadelphia (IASIP) is currently airing its 17th season, and it seems like the showrunners still have plenty of tricks up their sleeves. Making sure the longest-running live-action comedy remains on our TV screens is no small feat, but IASIP has the magic touch and a relentless, vastly talented cast and crew who continue to deliver.

It’s almost impossible to pick only ten out of 177 episodes that have aired so far, but some are more memorable than others. The ten most entertaining IASIP episodes are a mix of iconic and genuinely funny moments, even sparking some controversy and debate. They all boast creativity in its purest form and a group of friends and longtime collaborators who know where they wish to take their most lucrative project.

10

“The Gang Beats Boggs”

Season 10, Episode 1 (2015)

“The Gang Beats Boggs” is one of the more underrated IASIP episodes, but genuinely one of the funniest and most entertaining. The gang tries to beat Wade Boggs’ record of drinking “between 50 and 70 beer cans” on the flight from Philadelphia to Los Angeles; they take note by adding notches on each other’s t-shirts, while a lot of other things happen meanwhile.

Dennis (Glenn Howerton) and Frank (Danny DeVito) enter their own competition to make the mile-high club; Mac (Rob McElhenney) smuggles a case of beer into the cargo load, and Dee (Kaitlin Olson) and Charlie (Charlie Day) give Boggs a run for his money by drinking excessively and then hallucinating from the amount of alcohol. The episode is ridiculous and incredibly entertaining because the gang can’t stay calm and non-chaotic even on a cross-country flight. In a way, they’re also able to enjoy life’s small things, since hopping on a flight across the US just to beat a hearsay record feels like living life to the fullest. As messy and self-centered as they tend to be, “The Gang Beats Boggs” shows the gang kind of loving life, too.

9

“The D.E.N.N.I.S. System”

Season 5, Episode 10 (2009)

“The D.E.N.N.I.S. System,” is one of IASIP‘s most iconic episodes because it shows Dennis in full force, giving him a bit more context as a character. This insight, however, doesn’t really paint him in a positive light, but rather shows that he’s toxic, manipulative, and calculated in a lot of things, including his relationships with women. The D.E.N.N.I.S. system essentially means hooking women to his story, getting them to go completely wild over him, and then gaslighting and eventually dumping them. Still, this episode, as wacky as it gets, is quite entertaining as Dennis’ system actually fails big time.

The gang tries to employ his tactics, especially Charlie, who wishes to win over The Waitress (Mary Elizabeth Ellis), but, of course, the tactics are terrible and don’t really work; on the other hand, Dee suspects that her current boyfriend is using the D.E.N.N.I.S. system on her, and she sabotages the relationship by running away and spending the night in a bush. It’s amusing to watch just how seriously everyone takes Dennis—especially he himself—and how they just don’t know what to do in dating situations.

8

“Frank’s Pretty Woman”

Season 7, Episode 1 (2011)

Season 7 starts with a bang, and it’s arguably Always Sunny‘s greatest season; it has some of the most iconic IASIP episodes, including “Frank’s Pretty Woman.” The season opens with Frank deciding he wants to marry his favorite prostitute, Roxy (Alanna Ubach), and Dee wants to give her the Pretty Woman treatment and clean her up. Charlie wishes to introduce Frank to a more decent woman, so he poses as a millionaire on a dating app, and Mac inexplicably appears 50 pounds heavier, which concerns Dennis, who takes him for a health checkup.

The appearance of “Fat Mac” is an iconic TV moment; he later explains how and why he gained all that weight, but McElhenney’s dedication to making Mac a realistic person with weight fluctuations feels like he respects the viewers and, well, just being human. Mac gets super-ripped later, which is another dramatic transformation, but it’s so funny to watch the gang’s shock after seeing Fat Mac for the first time. In this episode, Charlie also projectile vomits all over a limo, and it’s some of the funniest stuff you’ll have seen—unless you’re sensitive to other people puking.

7

“Hero or Hate Crime?”

Season 12, Episode 6 (2017)

“Hero or Hate Crime?” is one of those episodes you have to see to believe. It’s incredibly fun, fast-paced despite taking place in one room the entire time, and shows off the comedy chops and improv skills of the main cast. The chemistry between them is exceptional here, and it’s entertaining to watch them banter. This is also the episode where Mac, finally, comes out as gay and doesn’t retract the decision, but the way he arrives at the decision is hilarious.

“Hero or Hate Crime?” opens with a situation—Mac and Dennis are walking down the street, when Dee and Dennis are eating ice cream and Dee loses the lottery scratch ticket from her bag; as Mac and Dennis walk, they see the ticket and chase it, but find themselves under a hanging piano. Frank, from across the street, sees that Mac is about to get hit by the piano and yells out a slur to get his attention; Charlie saves Mac and the scratch ticket, and the gang goes to an arbiter to decide who gets the ticket. They also discuss whether Frank saved Mac or committed a hate crime. That scene is just one of IASIP‘s best cold opens; you have to see the rest of the episode to fully enjoy its ridiculous and entertaining ways.

6

“The Gang Goes on Family Fight”

Season 10, Episode 8 (2015)

Another great episode from Season 10 is “The Gang Goes on Family Fight,” and it’s entertaining because it allows the gang to shine individually and as a group. Family Fight is the show’s counterpart to real-life’s Family Feud, hosted by Steve Harvey, and by Keegan-Michael Key as the unnamed host in IASIP. It’s hard to decide who stands out the most, though it’s one of the more underrated Mac episodes, for sure.

“The Gang Goes on Family Fight” opens with Dennis deciding everyone in the gang needs to take it down a notch and be normal for television. However, Mac has a problem with understanding the rules, constantly confusing the show with Jeopardy; Dee hasn’t eaten to look slim and wishes to show off her Jenny McCarthy-like comedic skills; Dennis has a problem with the buzzer sound, and Frank wants to include his right-wing politics into the show. Charlie becomes the star when he starts getting all the niche answers right. It’s pure chaos and a hilarious episode full of brilliant jokes, one of those you can watch and rewatch all the time.

5

“The Maureen Ponderosa Wedding Massacre”

Season 8, Episode 3 (2012)

“The Maureen Ponderosa Wedding Massacre,” aired on October 25, 2012, and it’s a parody of zombie horror movies to follow the Halloween theme. The episode has great production value and a tight script, ending the surreal theme and vibe with a reality-check, grounding us back into the IASIP universe by, inescapably, causing the most damage to Dee (as usual). The standout of the episode, though, is Howerton as Dennis, in all of his attempts to get Maureen to sign papers that will relieve him of paying her alimony.

The episode is, admittedly, bizarre in some ways, too—it shows the McPoyle family and their peculiarities, including Guillermo del Toro in a cameo as Pappy McPoyle, a senior family member. The gang attends the wedding of Maureen Ponderosa and Liam McPoyle; Frank gets bitten by a bat, and Dee sucks out the poison and accidentally swallows it. The wedding party begins acting like a horde of zombies at some point, and the story is told as a flashback from various perspectives. Even if bizarre and horror-ish, this IASIP episode is one of their most creative and entertaining ones.

4

“The Gang Goes to the Jersey Shore”

Season 7, Episode 2 (2011)

Most people remember “The Gang Goes to the Jersey Shore” by the rum ham that became a silent IASIP icon. The episode belongs among the most hilarious ones, and it’s part of the seventh season, which boasts some of the most brilliant IASIP episodes to date. Dennis and Dee reminisce of the time they used to go to the Jersey Shore for summer holidays, and ask the gang to come along. Charlie is terrified of traveling outside of Philadelphia, so the gang drugs him; Frank soaks a ham in rum to combine food and drink in one fun item, and Mac, now being overweight, feels compelled to enjoy the ham with Frank.

It’s tough to pinpoint the funniest part of the episode, because all of it is great. If we had to pick, maybe it’d be Frank and Mac finding themselves in the middle of the ocean after eating too much of the rum ham and falling asleep in a rubber boat. Their physical fight is hilarious, especially since the cause is losing the ham. We also get to see Charlie make his dreams come true by spending the night on the Jersey beaches with The Waitress. It’s one of the show’s greatest moments and a highly rewatchable episode.

3

“The Nightman Cometh”

Season 4, Episode 13 (2008)

“The Nightman Cometh” isn’t just iconic—it was turned into an actual musical. The talented cast of IASIP (who are also its creators) adapted the episode into a musical that was short-lived but still garnered a lot of attention; everyone reprised their roles, just like in the episode. Besides being historical in many ways, “The Nightman Cometh” is pretty hilarious and entertaining; Charlie Day wrote most of the music and lyrics, and though everyone in the cast is pretty talented and versed in music, Day is arguably the most versatile performer of the cast.

“The Nightman Cometh” shows Charlie finally finishing his play of the same name. He asks the gang to set up the play and star in it, but his ultimate wish is for The Waitress to see the play and become impressed by his skills. Realistically, the play is pretty terrible, but, in IASIP terms, it’s pure genius. The lyrics are clever, the acting is pretty ingenious, and the cast are at their greatest and most creative, which is a tough criterion, considering most of their episodes are great.

2

“CharDee MacDennis: The Game of Games”

Season 7, Episode 7 (2011)

If you’ve ever wished to invent your own kind of board game, take note from IASIP‘s “Chardee MacDennis: The Game of Games.” Mac, Dennis, Charlie, and Dee invented the game they aptly named CharDee MacDennis, and it consists of three levels: mind, which includes trivia and puzzles; body, including physical endurance; and spirit, which is the toughest and includes emotional battery and public humiliation. The game opens with a Wine and Cheese Reception where the teams respectfully cheer each other on, and then the real game begins. This time, the gang involves Frank and the audience is put in Frank’s shoes when learning the rules for the first time.

CharDee MacDennis is a corrupt game, as you might suspect; the gang usually cheats, with Dennis and Dee especially excelling in that. It’s also cruel, especially in the third phase of the game, but it’s interesting to see the gang play the game with such enjoyment and dedication. It’s a funny episode and fun to watch because of the brilliant performances, wild game rules, and the iconic status the game—and the series—reached because of the episode.

1

“Charlie Work”

Season 10, Episode 4 (2015)

Season 10’s “Charlie Work” is maybe the show’s greatest standout because of its cinematography and the creativity employed in crafting it. A big portion of the episode is a single take, following the hero of the story, Charlie, and the one day he pulls all the stops to make Paddy’s Pub functional. In the end, he turns out to be the reason Paddy’s is still open in the first place, considering the number of sanitary rules it’s actually breaking.

The Always Sunny episode follows Charlie preparing for a sudden arrival of a health inspector, while Mac, Dennis, Dee, and Frank have a plan of their own that involves a truck full of live chickens and steak meat, with the pub as the central point of their plan. Charlie tackles the gang’s plan at the same time as making the pub spotless for the inspector’s visit, showing his efforts in a 10-minute single-take scene. The episode was praised by critics and audiences alike for its style, humor, and ingenuity; it’s truly one of the most entertaining and interesting episodes of IASIP, often considered the showrunners’ best effort.

NEXT: The Best ‘It’s Always Sunny in Philadelphia’ Episodes, Ranked According to IMDb