5 Essential It's Always Sunny In Philadelphia Episodes Everyone Should Watch At Least Once

There are a lot of truly amazing episodes of the long-running FX sitcom "It's Always Sunny in Philadelphia." Over 16 seasons, the five miscreants known as "the gang" have gotten up to all kinds of shenanigans, with the comedy in each episode ranging from low-art nonsense like poop gags to jokes like "the implication" that are much, much darker. It can be a bit daunting to look at all of those seasons, but there are a handful of "Always Sunny" episodes that everyone should check out, whether they decide to watch the rest of the series or not. After all, it's the longest-running live-action American sitcom of all time, and it's had an impact on pop culture, even if it's somehow never won any major industry awards.

There are honestly dozens of episodes that I could recommend because the show has such a wide variety of killer episodes with some super meme-able moments. (Seriously, who on the internet hasn't used the Charlie Pepe Silvia gif at some point?). With that said, here are five of the most essential episodes of "It's Always Sunny in Philadelphia."

One thing that defines the gang is the pecking order, and bottommost member Charlie (Charlie Day) often gets treated the worst. In the season 4 finale "The Nightman Cometh," however, Charlie is in charge when he writes a musical starring the gang in an attempt to woo his love interest, the Waitress (Mary Elizabeth Ellis), into marrying him. (She declines.) The gang rehearse and then perform Charlie's musical for a live audience, telling the story of a princess who works at a coffee shop and falls in love with the Dayman after he overcomes both the Troll and the Nightman, who are likely fictionalized versions of Charlie's pedophile uncle Jack (Andrew Friedman).

"The Nightman Cometh" features singing and dancing from Dennis (Glenn Howerton) as the Dayman, Dee (Kaitlin Olson) as the princess, Mac (Rob McElhenney) as the Nightman, Frank (Danny DeVito) as a troll, and Charlie as himself at the end. Its songs — which were created by Day, "Always Sunny" writer and Rickety Cricket actor David Hornsby, and composer Cormac Bluestone — are also surprisingly catchy and funny little bops that feel like something the fictional Charlie really wrote (in pictograph form).

Look, "The Nightman Cometh" was so popular that the "Always Sunny" cast even took the musical within the episode on a six city live tour in 2009. That's pretty huge, and there are references to the Nightman throughout the rest of the series, making "The Nightman Cometh" vital to "Always Sunny."

The first season of "It's Always Sunny" has some funny episodes, but unfortunately, there's no Frank because DeVito didn't join the cast until season 2. Frank ended up being the secret sauce to making the show truly amazing, and in the season 2 episode "Dennis and Dee Go on Welfare," we get to see him shake everything up to hilarious effect for the first time after moving in with Charlie at the beginning of the season. You see, Frank is wealthy and funds the gang's antics, and his wealth (and some shady business practices) are what keep the bar afloat even when the gang is doing anything but bartending.

In "Dennis and Dee Go on Welfare," Dennis and Dee try crack cocaine in an attempt to get on welfare after Frank asks them to do too much work at the bar, which sends them into a downward spiral. Charlie then finds a loophole where people on welfare will do their jobs for them and then decides to celebrate with Frank's money. That means we get to see the very proud Dennis and Dee filthy and begging for drugs from Mac and Charlie wearing tuxedos and riding in a limo, completely upending the status quo. The episode is noteworthy for Dennis and Dee singing Biz Markie's "Just a Friend" on a stoop, but it's also full of great moments and helps establish just how much the "Always Sunny" writers are willing to push the envelope.

The gang are all pretty funny, but they're also surrounded by a larger cast of totally ridiculous side characters. Some of the best episodes show the gang bringing their whole crew together, which includes people like the free-spirited Artemis (Artemis Pebdani) and the expansive, inbred McPoyle family. In "Who Got Dee Pregnant?," the guys try to figure out who the father of Dee's baby is by trying to remember their Halloween party, the night they believe she got pregnant. The only problem is that they drank a lot and don't remember, so we see different versions of what might have happened, leading them to eventually ask both Artemis and Liam (Jimmi Simpson) and Ryan (Nate Mooney) McPoyle for help.

"Who Got Dee Pregnant?" is great because it shows us just how deluded the gang can be about their own lives, and it also gives us some truly ludicrous McPoyle moments, including Mac hooking up with Liam and Ryan's mute sister Margaret (Thesy Surface) and Liam's screaming demands that Mac call her. It also gives us Frank dressed as both Spider-Man and Man-Spider, as well as some amazing drunk acting from the whole gang. (Fun note: Olson was really pregnant during filming, so the show's cast and crew had to try and hide this during the flashbacks, which is kind of fun to look for.)

The gang has always been more than a little twisted, but season 7 felt like when they really stepped things up to another level. The first two episodes of the season feature a sex worker dying in Charlie and Frank's apartment, as well as Dennis and Dee smoking angel dust and witnessing a robbery gone very violent. Things only continue to spiral hilariously out of control from there. In episode 7, "Chardee Macdennis: The Game of Games," we learn that one day, while the gang was bored, they created their own board game, and it's just as dangerous and wild as the gang itself. Dennis and Dee form one team, the "Golden Geese," and apparently they always win, destroying not only Mac and Charlie's self-esteem but their game tokens as well.

"Chardee MacDennis" is one of the only episodes to get a sequel or direct follow-up because it's a ridiculously fun half-hour with some of the series' most-quotable moments. ("Because Dennis is a bastard man!" is funny no matter what.) We get to see each member of the gang's strengths and weaknesses and also learn that Dennis and Dee have always cheated (because, naturally, cheating is encouraged and they're never the types to play fair at anything). It's full of insights into the gang and its dynamics while being really freaking funny to boot, so how can you not love "Chardee Macdennis?" Just be careful if you try playing the game yourself!

The members of the gang are truly terrible people, but the creatives behind "Always Sunny" seem to have their hearts in the right place. As a result, we occasionally get episodes that are about much more than whatever silliness the gang is up to. One of the best episodes that digs into tricky topics is "Hero or Hate Crime?" from season 12, which is when Mac finally comes out of the closet as a gay man. Mac's sexuality wasn't predetermined from the start, but eventually it made sense for him to come out as gay, and the show had to do it in a way that felt true to "Sunny." "Hero or Hate Crime?" is a seriously vulgar half-hour of TV as the gang tries to determine what words are acceptable for each of them to say, including and especially a particular slur for gay men. Mac explains the horrible history of the word and they agree to not use it again, and eventually, he comes out of the closet in order to receive the winnings of a lotto scratcher.

McElhenney has several LGBTQ family members, including his mother and her long-term partner, so he wanted to make sure the episode dealt with things in a way that wasn't hurtful to anyone yet still maintained that special "Sunny" sense of humor. The best part? After Mac comes out, the gang all agree that they still hate him and find him annoying, but it has nothing to do with his sexuality. "It's a Mac thing," they agree, and it's amazing because they're still the same terrible characters, and they always will be.

Season 17 of "Always Sunny" will premiere on FXX on July 9, 2025, and will be available to stream the next day on Hulu.