The best episodes ofIt’s Always Sunny in Philadelphiahighlight the show’s unique sense of humor and its hilariously flawed main characters. Created on a microbudget by stars Rob McElhenney, Glenn Howerton, and Charlie Day,It’s Always Sunny in Philadelphiais an outrageous sitcom exploring the grim and destructive lives of the gang at Paddy’s Pub. With Kaitlin Olson and Danny DeVito also starring,It’s Always Sunnycreated one of television’s most beloved ensembles by making these characters some of the worst people on television.

With 16 seasons and counting,It’s Always Sunny in Philadelphiahas become one ofthe longest-running sitcoms of all time. While that leaves a lot of episodes for new fans to explore, there are a select few that stand out as the best the series has to offer. These episodes highlight how ridiculous these characters are, embrace their darkest tendencies, and even subvert the audience’s expectations of what an episode ofIt’s Always Sunny in Philadelphiacan be like.

The gang yelling at Frank in the bar in It’s Always Sunny in Philadelphia

10The Gang Gives Frank An Intervention

Season 5, Episode 4

While the original cast members helped bring the show to life, the casting ofDanny DeVito inIt’s Always Sunny in Philadelphia’s second seasonchanged it for the better. Frank Reynolds became the most disgusting member of the group and this episode highlights that. “The Gang Gives Frank an Intervention” sees Frank coming to the realization that he might not have many years left alive and he wants to get “real weird with it.” This leads to the rest of the gang stepping in to set him straight.

While the title might suggest the gang showing real concern for one of their members, they actually just want to stop Frank from being so annoying. In fact,the episode has a lot of fun displaying how these are the last people who should be trying to steer someone in the right direction. There is also a hilarious running gag in which they keep suggesting interventions for each other’s shortcomings, including Charlie’s illiteracy.

Dee, Dennis, Charlie, and Mac sat together arguing in the arbitrator’s office

9Hero Or Hate Crime?

Season 12, Episode 6

There is a lot of talk about what is acceptable in comedy these days, but despiteIt’s Always Sunnyhaving several banned episodes, it has also proven it can keep pushing the boundaries with its humor. “Hero or Hate Crime?” is an ideal example of the show’s bold comedy as it finds the group hiring an arbitrator to resolve a situation in which Frank may have saved Mac’s life, but he used an offensive slur to do so.

Apart from the flashbacks to the incident in question, this isa fantastic bottle episode ofIt’s Always Sunnythat shows the fun that can be had putting these dysfunctional characters in a room together and simply letting them argue. However, it also was an early sign of the show evolving with its storytelling as it addresses Mac’s sexuality in a more direct way, leading to a surprisingly touching conclusion.

Frank Dee and Charlie in The Gang Buys A Boat in It’s Always Sunny in Philadelphia

8The Gang Buys A Boat

Season 6, Episode 3

Another way in which Frank was a great addition to the series is that he could fund all of the gang’s wildest ideas. “The Gang Gets a Boat” is a perfect example of how the show could take the simplest of scenarios and just allow these characters to make a mess of it. After buying the boat, which needs a lot of work, Frank, Charlie, and Dee get to work cleaning it up while Mac and Dennis attempt to turn it into the ultimate party venue.

There are some wonderful moments of hilarity as the gang proves they have no business being on the water. Kaitlin Olsen continues to prove herself the most talented physical comedian in the ensemble, with Dee learning dance movies from an inflatable tube man. However,the stand-out moment in the series is Dennis describing his dark theory of “the implication"of inviting women to party out on their boat. It is a key moment in cementing Dennis as a villain.

Mac, Frank, Charlie and Dee sitting in Dennis' car as he drives in It’s Always Sunny in Philadelphia.

7The Gang Hits The Road

Season 5, Episode 2

While the show has ventured to different places in more recent years, including anentire season ofIt’s Always Sunnyset in Ireland, “The Gang Hits the Road” was the first time the characters decided to get out of Philadelphia. The gang decides to visit the Grand Canyon but finds that their adventures are continuously waylaid by their constant attempts to turn this into the perfect road trip.

It is a lot of fun seeing these characters fail at even the smallest attempts to broaden their horizons. With all the frequent stops along the way, there are endlessly hilarious moments for the characters, from picking up a young hitchhiker to Charlie trying fruit for the first time to Dennis and Charlie accidentally poisoning themselves in the trailer. It all builds to the hilarious conclusion that they fail to even leave Philly.

The gang play Chardee Macdennis in It’s Always Sunny in Philadelphia

6Chardee MacDennis: The Game Of Games

Season 7, Episode 7

While game nights with friends can be a lot of fun, it makes sense that the gang would turn such an activity into an aggressive, offensive, and meanspirited evening. While hanging out at the bar with nothing to do, the younger members of the gang decide to introduce Frank to the board game they invented years ago, Chardee MacDennis (named as a combination of their names). As they play, it becomes clear that it is a ridiculous and horrific game that only these people could come up with.

The game obviously includes a lot of drinking, but also categories such as “emotional battery” and “public humiliation”. Frank acts as the audience surrogate as he is taken through the nonsensical game and its ever-changing rules with the confusion of it all making it even funnier. However, the episode is a great highlight of how these people are terrible friends but are also strangely perfect for each other.

Dennis goes over the The D.E.N.N.I.S System in It’s Always Sunny in Philadelphia

5The D.E.N.N.I.S. System

Season 5, Episode 10

Dennis' villainous arc onIt’s Always Sunny in Philadelphiawas gradual at first, but this is one of the episodes that fully embraced him as a dark and twisted man. “The D.E.N.N.I.S. System” is a hilariously dark episode in which Dennis reveals his method for seducing women before cutting them out of his life completely, which includes manipulation and emotional torture. While Dennis tries to prove he can work the system on a girl he already used it on, the rest of the gang take their own unique approaches to the method.

Glenn Howerton gives a tour-de-force comedic performance in this episode, and is clearly having a ton of fun at embracing all the worst traits in the character. While Dennis' actions are reprehensible and unsettling, the series keeps it funny by showing how pathetic he is at the center of it all. Also, while Dennis' villainy takes center stage, the episode also shows that the rest of the gang is not much better.

Charlie looking stunned in the It’s Always Sunny in Philadelphia episode “Charlie Work."

4Charlie Work

Season 10, Episode 4

Charlie is often seen as the most incompetent and dim-witted person in the gang, but “Charlie Work” gives a look behind the scenes of his job on a particularly hectic day at Paddy’s Pub, suggesting he might be the most important member of the team. With deliveries and health inspectors coming to visit the pub, Charlie frantically attempts to get everything ready while the rest of the gang offers no help or recognition of his hard work.

The episode is directed by Matt Shakman, director ofthe upcomingFantastic Four: First Steps, and it is clear “Charlie Work” has a more cinematic feel.The episode is told in real time and shot as one continuous take, giving it a sense of tension and relentlessness that adds to Charlie’s determination. It manages to score laughs as Charlie pops in and out of the other conversations, making for a unique and hugely satisfying episode.

Charlie cuts the brakes and jumps out the car because hes the widlcard in Its Always Sunny In Philidelphia

3The Gang Solves The Gas Crisis

Season 4, Episode 2

One of the best recurring themes of the show is that the gang is filled with arrogance while also being oblivious to how dumb they really are. This brutal combination leads them to attempt to solve complex situations with hilarious results. “The Gang Solves the Gas Crisis” sees Dennis, Mac, and Charlie upset about rising gas prices and deciding that they will start selling gas themselves.

What makes the episode special is how it attempts to break down this very strange group dynamic with each of them having their own strengths to play in the operation. This creates a hilarious running gag as Charlie is all too eager to embrace his role as the group’s “wild card”, creating an oil tycoon character and threatening to blow up several gas stations. The aimlessness of the gang’s mission is made funnier by their constant confidence that they are smart enough to figure this out.

Mac and Dennis sitting at a dinner table in It’s Always Sunny in Philadelphia

2Mac & Dennis Move To The Suburbs

Season 11, Episode 5

It is made clear throughout the series that the Paddy’s Pub gang can operate within their own strange sphere of existence, but as soon as they attempt to interact with the rest of the world it becomes a disaster. After Mac and Dennis suggest that they would like the move to the suburbs, Frank makes them a bet that they wouldn’t be able to last in such an environment because they are “city scum”, they seek to prove him wrong.

It is another darkly comedic episode of the series, with it taking hilariously little time for the duo to run into issues and frustrations with their new life, from the commute to work to boring life at home to annoying neighbors. Mac and Dennis have always had a twisted relationship and this episode wonderfully highlights their married-couple dynamic in a grim way.

Blended image of The Nightman Cometh

1The Nightman Cometh

Season 4, Episode 13

The Nightman was previously established as part ofIt’s Always Sunnylore, but the concept took on a life of its own leading to this wonderful musical episode of the series. Charlie reveals to the gang that he has written a musical, supposedly without any ulterior motives, and seeks their help to stage it. Of course, the rest of the gang has their own vision of the material, including Mac’s cat eyes, Dee’s objection to the lyrics, and Frank’s problematic pronunciation of some of the lyrics.

It is a lot of fun seeing Charlie so passionate about the project which leads to his taking charge of the group, a rarity in the show. However, as passionate as he is, the musical is as strange, incoherent, and surreal as can be expected from Charlie’s mind. Nonetheless, the songs are as catchy as they are funny, with the musical episode becoming so popular that the cast ofIt’s Always Sunny in Philadelphiaactually took it on the road.

It’s Always Sunny in Philadelphia

Cast

It’s Always Sunny in Philadelphia is a television series that premiered in 2005, chronicling the chaotic lives of four self-involved friends running an Irish pub in Philadelphia. Their misguided decisions and skewed perspectives often result in amusing and uncomfortable situations, complicating their professional and personal relationships.