The best episodes of It’s Always Sunny in Philadelphia highlight the show's wild humor, outrageous characters, and willingness to tackle any subject. The sitcom has managed to stay consistently hilarious over the course of nearly two decades creating countless hilarious episodes. As good as the entire run has been, the best episodes of It’s Always Sunny in Philadelphia really stand out as examples of the best the show has to offer.
It's Always Sunny in Philadelphia season 16 has arrived to continue the absurd and deranged antics of the gang at Paddy's Pub. Of course, these new episodes are still competing with the best highlights from the series. From tackling big topical issues with a clever approach to showcasing the characters' worst attributes in hilarious ways to make the audience laugh at some truly dark material, these are the best episodes of It's Always Sunny in Philadelphia.
20 The Waitress Is Getting Married (Season 5, Episode 5)
Romance on It's Always Sunny in Philadelphia is never successful, but there is something to be said about how long Charlie and the Waitress have remained connected. Of course, that has to do with Charlie obsessively pursuing her despite no interest on her part. This episode deals with Mac and Dennis deciding to set Charlie up on a date to avoid him potentially losing control when he learns the Waitress is getting married. From the disastrous dating profile to the sweaty date itself to Charlie eating a block of cheese to calm his nerves, the episode has endless fun with how bizarre Charlie truly is.
19 The Gang Gives Frank An Intervention (Season 5, Episode 6)
It can be hard to introduce a new character into a sitcom ensemble, but Danny DeVito joining It's Always Sunny in Philadelphia in season 2 changed the show for the better. DeVito fully committed to the disgusting and unhinged character of Frank Reynolds to the point that the rest of the gang feels he has gone too far. This episode finds the others staging an intervention for Frank only for the specialist they hired to identify the entire group as in need of some serious help. Frank's depravity is a highlight but watching the characters turn an intervention into them drunkenly pointing out each other's faults makes for a hilarious climax.
18 The Gang Gets Held Hostage (Season 3, Episode 4)
It's Always Sunny is a rare show that can turn a bottle episode into one of its most exciting installments. It sees the welcome return of the McPoyle family, the gang's main adversaries, who take the gang hostage inside Paddy's Pub. Throwing these characters into a high-stakes, a life-or-death scenario like this is brilliant and made only better with the McPoyles pull the strings. The gang quickly makes it everyone for themselves, succumbs to Stockholm syndrome, and turn on each other all while Frank is doing a hilarious Die Hard parody in the vents of Paddy's Pub.
17 CharDee MacDennis: The Game Of Games (Season 7, Episode 7)
Like "The Gang Gets Held Hostage," the episode "CharDee MacDennis: The Game of Games" recognizes that sometimes the show is at its best when it just focuses on the gang together in the pub. Such is the case with the hilarious and deranged episode in which the gang plays a game they made up themselves. The increasingly strange requirements and nonsensical rules escalate as the gang gets more enraged at each other. It is an almost charming reminder that, despite everyone hating these people, the gang has found an odd and destructive kinship with each other.
16 The Gang Gets Analyzed (Season 8, Episode 5)
There are few characters on television in more need of therapy than the gang from It's Always Sunny. That simple concept sets up the hilarious episode in which Dee invites the whole gang to her therapy session, not in an attempt to heal themselves, but rather to get an outside party to decide which of them needs to do the dishes following a dinner party. Seeing each of the main characters individually go in for a session and reveal their bottomless pit of issues is a thrill to watch and is one of the most insightful episodes of the series when it comes to these characters.
15 Time's Up For The Gang (Season 13, Episode 4)
The show has never shied away from dealing with the biggest issues of today in the most outrageous ways. So it's no surprise they tackled the #MeToo movement with the same kind of absurd hilarity. The episode finds the gang attending a seminar on workplace harassment and inappropriate behavior. Of course, they derail the entire seminar with their own bad behavior and find themselves facing a lot of trouble. It's a hilarious reminder of just how terrible each of these characters has been throughout the series.
14 The Gang Tries Desperately To Win An Award (Season 9, Episode 3)
Despite its record-breaking run on television and its countless fans, the show has never really been recognized by the awards community. While the show doesn't need accolades to be funny, this episode pokes fun at why this unconventional sitcom fails to connect with the mainstream. The episode follows the gang as they try to rebrand Paddy's Pub so it can win the award for the city's best bar. The episode pokes fun at the so-called popular shows while also poking fun at themselves for being so weird and outrageous. Even if It's Always Sunny never won Emmys, episodes like this prove its brilliance.
13 The D.E.N.N.I.S. System (Season 5, Episode 10)
Throughout the series, Dennis Reynolds has devolved from a self-centered ladies' man to a full-blown psychopath. His methods for seducing women have always been creepy, but this episode takes a peek at his true madness. The D.E.N.N.I.S. System is a carefully planned strategy in which Dennis seduces women through lies, psychological torture, and manipulation. As disturbing as his methods are, it's satisfying to see him fail so miserably as the rest of the gang attempts to develop their own take on the system.
12 Mac & Charlie Die (Season 4, Episode 5)
An episode in which two characters fake their own deaths would seem pretty farfetched for just about any other show but it's business as usual for It's Always Sunny. Mac and Charlie decide to stage their epic deaths after Mac's dad is released from prison and they suspect he'll come for them. From the idiotic way Mac and Charlie go about their plan to the rest of the gang's unbothered reaction, it is a hilariously dark misadventure for the show.
11 A Very Sunny Christmas (Season 6, Episode 14)
Even a show like It's Always Sunny can get in the holiday spirit with its own Christmas special. Of course, it is a much darker and more disturbing take on this festive time of year. As Charlie and Mac go about their annual traditions, they uncover so unpleasant secrets about their childhood Christmases. Meanwhile, Dennis and Dee try to teach Frank a lesson for his mean-spirited Christmas traditions. The episode is especially vulgar and violent which feels appropriate for this show. There are some classic gags like Charlie's bloody encounter with a mall Santa and Frank's attempt to hide in a couch.
10 The Gang Goes To A Water Park (Season 12, Episode 2)
The Paddy’s Pub gang are so outrageous and generally terrible people, that putting them in just about any situation is going to be entertaining. This episode is a perfect example of that as a simple trip to the water park turns into one hilarious mishap after another. Being surrounded by people in a family-friendly environment is a recipe for disaster with this group and the episode takes full advantage of the setting. From Mac and Dee getting stuck in the waterslide, to Frank going to extremes to cut the line, it’s a perfect adventure for the gang.
9 The Gang Hits The Road (Season 5, Episode 2)
Though audiences had seen the gang travel more in the later seasons, this episode was their first attempt to actually leave their beloved Philadelphia. It goes about as well as you would expect. The episode is a perfect highlight of how the gang can’t help but get in their own way. They become so preoccupied with creating the perfect road trip that they prevent themselves from actually leaving town. The episode has some laugh-out-loud moments, such as the constant attempts to ditch Dee. And it all ends with a hilarious anti-climax.
8 Hero Or Hate Crime? (Season 12, Episode 6)
The show has always pushed the envelope and, so far, has done so without going too far. To have a full episode surrounding the use of a homophobic slur was risky, but it managed to be both thoughtful and hilarious. The show can achieve so much by just having these characters argue with each other. That’s pretty much all that this episode is about, as they try to determine ownership of a lottery card. The episode is also noteworthy for concluding the long-running question of Mac’s sexuality, which continues to be an important part of the show going forward.
7 Mac & Dennis Move To The Suburbs (Season 11, Episode 5)
These characters are, thankfully, not your everyday people and they are not able to live like normal people. Whenever confronted with how the rest of society works, these characters usually begin to fall apart. This episode features maybe the most revealing proof of how messed up these people are. Taking on a bet from Frank, Mac and Dennis move out to the suburbs to start a new life. Quite quickly, the change in environment begins to get to them and they both lose their minds in very dark ways.
6 The Gang Dines Out (Season 8, Episode 9)
The Paddy’s Pub gang is one of the most unique groups on television. Like most sitcom friends, they seem to spend all their time together and do everything together. However, unlike other groups, they also seem to have a lot of animosity for each other. This episode finds the gang split in teams as they try to enjoy a special meal while at the same restaurant. What follows is a lot of tension, resentment, and mistreatment of waiters. It’s further proof that these people probably only hang out with each other because no one else will.
5 The Gang Buys A Boat (Season 6, Episode 3)
Not only is Danny DeVito a welcome addition to the cast who seems game for anything, but Frank’s enormous wealth allows the gang can do anything that pops into their minds. This episode is another one of the simple premises out of which the show squeezes every potential for comedy. While Charlie’s ocean garbage collection and Dee’s new dance moves are hilarious, the episode’s highlight is Dennis’ very disturbing description of “the implication,” further cementing him as a true psychopath.
4 The Gang Solves The Gas Crisis (Season 4, Episode 2)
Part of what makes this show special is how it actively tries to be different from other shows. The brains behind It’s Always Sunny are very aware what other comedy shows are doing and always try to pervert those old tropes. This episode explores the standard personalities that make up a regular pop culture group – the brains, the looks, the muscle, etc. The problem is none of these people really have any of these could qualities and thus they can’t accomplish anything. Extra points though for introducing Charlie as the “wild card."
3 Sweet Dee Has A Heart Attack (Season 4, Episode 10)
Some of the greatest episodes of the show present a typical, relatable issue and then show how badly the gang can screw it up in their own ways. In this episode, the gang seek a healthier lifestyle and, obviously, fail. Dennis and Dee try to achieve perfection in the easiest way possible. Frank is put in a mental institute, in an homage to DeVito’s role in One Flew Over the Cuckoo’s Nest. But the highlight is Mac and Charlie seeking health insurance by getting a mailroom job. This leads to the meme-worthy moment where Charlie tries to unwrap a vast conspiracy that is all in his simple mind.
2 Charlie Work (Season 10, Episode 4)
Charlie Kelly is one of television’s strangest characters. He is an anger-prone, illiterate adult who should be dead from all the glue-huffing and paint-drinking. And yet, this episode shows that there might be a little more going on inside Charlie’s mind. As they prepare for a visit from the health inspector, Charlie tries desperately to get the pub and the gang ready. Shot like a single take, the episode is filled with energy and fun as Charlie does what he does best. And the slow-burn gag with the barstool is just icing on the cake.
1 The Nightman Cometh (Season 4, Episode 13)
It’s Always Sunny in Philadelphia is one of those great shows that reward loyal viewership. For the Season 4 finale, the show took a small but memorable gag from Season 3 and created a musical episode around it, and it was wonderful. In an attempt to finally woo his crush, Charlie puts on this elaborate, nonsensical and accidentally obscene stage production. The episode is funny enough just watching the gang try to wrap their heads around the absurdity of Charlie’s musical. Add to that the fact that the songs are actually pretty entertaining. It further proved that this show could do anything and fans have been waiting for a sequel to "Nightman Cometh" ever since.