The 10 Most Hilarious Episodes of ‘It’s Always Sunny In Philadelphia’

It’s Always Sunny in Philadelphia has been on an extraordinary journey over the past 15 years. Initially starting out as a film idea by struggling actors, it has gone from a cult hit to a flagship show for FXX.

The show was largely boosted by the fantastic introduction of Danny DeVito as Frank Reynolds in season two. However, the premise of five narcissistic underachievers who run a dilapidated Irish pub in Philadelphia proved to be both unique and hilarious. Unlike other sitcoms, the characters are despicable, selfish, appalling, and unethical, which always results in controversial, un-PC, and wildly entertaining episodes.

10. “The Gang Gets Analyzed” (Season 8, Episode 5)

By the time we reach season eight, it is quite clear that each member needs some kind of therapy.

This fantastic episode explores each character’s psyche as they have one-on-one sessions with Dee’s therapist. All to determine who should do the dishes after a meal they had.

Each session is brilliant in its own right, complete with Mac’s body issues, Charlie banging his head on the wall, Frank opening the floodgates, and Dee’s compulsive lying. But, it’s Dennis who has the best session. He tries to work with the therapist and reveals psychological dossiers he has been keeping on everyone in the gang. He even has a profile on his sister Dee dating back to second grade.

“The Gang Gets Analyzed” is an excellent exploration of each character’s extreme flaws. However, hilariously the gang doesn’t care about improving themselves. They simply want to know who should do the dishes. Source:

9. “The Gang Hits the Road” (Season 5, Episode 2)

The gang decides to go on a trip to the Grand Canyon in “The Gang Hits the Road”. Unfortunately, the trip is a complete disaster.

Although there is too much to summarize, some of the highlights include:

  • Mac knocking over a bicyclist with a beer can;
  • Searching an Italian market for a pear;
  • Dee picking up a hitchhiker to join in their drinking game, and;
  • Burning wicker chairs so they can cook hot dogs.

An eventful, road trip, indeed. Source:

8. “Chardee MacDennis: The Game of Games” (Season 7, Episode 7)

Essentially a bottle episode, “Chardee MacDennis: The Game of Games” takes place entirely within the bar as the gang looks to entertain themselves on a rainy day. Their solution is to play a game that they invented many years ago, which pits Charlie and Mac against Dee and Dennis. Mac and Charlie have never won before, so they get Frank on their team to try and change their fortunes.

Unsurprisingly, the game is deranged and involves a heavy amount of drinking. Plus, it contains all kinds of rules such as no cursing in level two and no questions allowed while the clock is running. To win, the team must progress through three levels:

  1. Level One (Mind): Trivia, Puzzles, and Artistry.
  2. Level Two (Body): Physical Challenge, Pail and Endurance.
  3. Level Three (Spirit): Emotional Battery and Public Humiliation.

It is the perfect recipe for one unforgettable episode. Source:

7. “The Waitress is Getting Married” (Season 5, Episode 5)

Whilst trying on wedding dresses for a fictional wedding, Dee makes the discovery that the Waitress (who Charlie loves) is getting married and to one of her ex-boyfriends (who she now wants back). Consequently, she tries to split them up by inviting them to an awful bachelorette party she organizes.

What makes this a classic episode, however, is Charlie’s woeful attempt at online dating — complete with the guidance of Mac and Dennis. They attempt to write a profile for Charlie, but quickly realize just how bizarre he truly is. Although they set up a date with a lawyer, it quickly turns into a complete car crash of a date. Despite this setback, Charlie ends the episode on a high as he learns that the Waitress is no longer getting married. Source:

6. “The Gang Solves the Gas Crisis” (Season 4, Episode 2)

This fantastic episode sees the guys explore their specific role within the gang. They come to believe that their plans fail because they ignore their roles. So with their roles established (Mac as the brains, Dennis as the looks, and Charlie as the wildcard), they attempt to sell gasoline door-to-door. When that fails, the boys realize they had the roles wrong all along. They settle on Dennis as the looks, Mac as the brains, Frank as the muscle, Charlie as the wildcard, and Dee as the useless chick. Source:

5. “Mac & Charlie Die” (Part 1 & 2) (Season 4, Episodes 5 & 6)

Technically two episodes, this story centers around Mac and Charlie. The two friends decide to fake their own deaths since they believe that Mac’s father is going to kill them. The equally hilarious side-story sees Frank and Dennis explore the world of anonymous sex after discovering a glory hole. To fake their death, they steal Dee’s car, leave a suicide tape and some of Charlie’s teeth (which simply fall out) and try to explode the car by driving it into a wall. The crash leaves Mac dazed and confused, seeing him become obsessed with a wedding dress which he begins to wear. Dee discovers Mac and Charlie living as “hobo drifters” on the roof and also fakes her death, and Frank clearly misses Charlie as he carries around a disturbing mannequin look-alike. This all reaches a brilliant climax, and it is a well-crafted hour long story with dozens of classic scenes. Source:

4. “Sweet Dee’s Dating a Retarded Person” (Season 2, Episode 9)

The show is most certainly not for those who are easily offended, particularly because of episodes such as this. Dennis claims that Dee’s new boyfriend, who is an up and coming rapper, is mentally handicapped, seeing the two of them attempt to prove each other wrong by keeping score. The real hilarity in this episode, however, is with the other plot, which sees the rest of the gang attempt to start their own rock band. They disagree on every single element of the band, but Charlie proves himself to be a musical prodigy (this becomes important throughout the show). In this episode he, with Dennis’ support, writes the now-famous song “The Dayman” whilst huffing spray paint in his apartment. Meanwhile, Dennis’s claims begin to get to Dee, who breaks up with her boyfriend. This then brilliantly blows up in her face at a gig at the bar. Source:

3. “The Nightman Cometh” (Season 4, Episode 13)

Charlie’s surprising musical talent was discovered in “Sweet Dee is Dating a Retarded Person,” and this is the episode where this is showcased in brilliant fashion. In order to win over The Waitress, Charlie writes an entire musical which reprises the bizarre Dayman and Nightman characters from the previous mentioned episode. Charlie claims the story to be about his transformation into the Dayman, who then fights the Nightman, but to everybody else it appears to be about a boy being molested by the Nightman. The rehearsals are hilarious as the gang infuriates Charlie by switching roles and improvising lines, plus the confusion over the line “boy’s soul.” The big night comes around with The Waitress sat front and center, but the show is a hilarious mess from start to finish. The theatrical side of things makes this one of the greatest episodes, and a fan favorite with many. Source:

2. “The Gang Gives Frank an Intervention” (Season 5, Episode 4)

The show really began to take shape once Danny DeVito joined in the second season, and his character’s hilarious demise is a huge part of the show’s success. He starts off as a wealthy businessman and attempts to be an authority figure, but after hanging around the gang for a while, he soon descends into depravity and he quickly becomes a great source of humor. This is best on show in this episode, where the gang decide to intervene with Frank after they realize he has “gone off the deep end” (although they do admire his wine in a can idea). The episode also introduces Gail the Snail, Dee and Dennis’s awful cousin, who they salt when she becomes too annoying, but admit “what kind of person salts another human being? There is no joy in salting someone. Everyone loses.” The intervention is, of course, a complete and spectacular disaster. Source:

1. “The D.E.N.N.I.S. System” (Season 5, Episode 10)

It’s Always Sunny is perhaps most famous for The D.E.N.N.I.S. System, which is Dennis’s foolproof system for seducing women, which he attempts to teach to the rest of the gang. The system, which is appalling and completely sociopathic, inspires Charlie to try it on The Waitress, whilst everyone (incorrectly) believes that Dee’s boyfriend is doing it to her. Dee bets Dennis that he cannot win back the girl he just used the system on, which reveals Mac’s own system (Move in After Completion), and Frank’s strategy to simply “feeds on scraps” by flashing $100 dollar bills and Magnum condoms “thus demonstrating I have a monster dong.” Dennis then concocts a master plan to get everyone what they want, but this of course goes awry in spectacular fashion. The system itself, and the male characters’ response to it, make this a fantastic, quotable, twisted and completely hilarious episode.–39-s-Always-Sunny-In-Philadelphia—The-D-E-N-N-I-S-System-scene–S05E10—The-D-E-N-N-I-S-System#lziK87hXARJ6sBJd.97 Source:
Jonny Hughes

Jonny Hughes

Jonny Hughes has been writing about movies and TV for Goliath since 2015.