10 Best It’s Always Sunny in Philadelphia Episodes

It feels odd to call the longest-running live-action sitcom of all time an underdog, but that’s what It’s Always Sunny in Philadelphia is. It’s always been something of a niche product; however, it’s definitely odd that the longest-running sitcom of all time has never even once won an Emmy. In fact, it’s only been nominated three times, and it wasn’t for Outstanding Comedy Series; it’s always been for stunt coordination. A series that proudly and brilliantly goes against the grain doesn’t receive as much love as a series that plays things safe within formulaic sitcom parameters.

Without a doubt, It’s Always Sunny in Philadelphia is one of the most ingenious shows to ever hit television. There’s even an argument to be made that it’s the funniest show of all time… at least for those who can get on its wavelength. The following episodes serve as illustrations of that substantial appeal.

Here are the 10 best episodes of It’s Always Sunny In Philadelphia.

1) “The Gang Exploits a Miracle” (Season 2, Episode 7)

Sunny Season 1 has its highlights, but it’s still very much a show in its infancy. Yet, even from the beginning, it was clear that It’s Always Sunny wanted to push boundaries, and it was capable of doing so in unexpected ways. But there was still something missing, and that something was Danny De Vito. Once his wealthy scumbag Frank Reynolds got involved in the sophomore season, there was a logical way for the gang to fund their schemes. But, even still, the best scheme of Season 2 (one of the series’ top years) is undoubtedly their exploitation of a water stain that vaguely resembles the Virgin Mary.

“The Gang Exploits a Miracle” is early Sunny at its best. There’s an opportunity to make money from something so unethical the vast majority of people wouldn’t even think of doing it. But the gang doesn’t think twice about doing it. They dive in. Plus, seeing Mac and Charlie pretend to be pseudo-priests is iconic. They’re not even doing that for money; they’re just trying to one-up each other. And Charlie wins, even though Mac is the religious one of the two. Truly top-tier bickering.

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

Season 4 is still early days Sunny, but it found the show taking bigger swings. This is never more evident than in “The Nightman Cometh,” which has the gang putting on an entire play. A really, really funny play.

Season 4 has a number of A-level classics, e.g. “The Gang Solves the Gas Problem,” “Mac’s Banging the Waitress” and “Mac and Charlie Die,” but “The Nightman Cometh” is arguably the best episode of the series. It’s not the first one you should show people, but it’s perfect. It’s also the only one to spawn an entire live stage tour.

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

If there’s a perfect episode to show an Always Sunny first-timer, “The Gang Gives Frank an Intervention” is it. You get a full sense of all the characters, and you get a great taste of one of the many elements that make the show so great: De Vito going wild.

It also has the single funniest scene of the show’s history, where Frank is walking down a suburban street, blacked out drunk and thinking out loud about how he’s going to “bang Aunt Donna.” Mac, who has been walking alongside him the entire time (out of frame), finally appears in the show and speaks, which scares Frank out of his mind.

Season 5 as a whole is arguably the series’ best. “The Gang Hits the Road,” “The Gang Wrestles for the Troops,” “Paddy’s Pub: Home of the Original Kitten Mittens,” “Mac and Dennis Break Up,” and “The D.E.N.N.I.S. System” are all classics.

4) “The Gang Buys a Boat” (Season 6, Episode 3)

Always Sunny is at its best when the gang has a simple plan and, through their own individual faults, that simple plan goes to utter goose s**t. That’s “The Gang Buys a Boat” to a tee. Frank and Charlie are obsessed with catching oysters; Dennis and Mac are obsessed with the others cleaning up the boat while they party, and Dee is just trying not to look like an inflatable guy from used car lots while dancing. Oh, well, Dennis also wants to have sexy times on the boat, and he thinks he should have an easy time doing it…because of the implication.

Season 6 was a step down from the perfection of Season 5, but there were still a few golden eggs, e.g. “Mac and Charlie: White Trash” and “Charlie Kelly: King of the Rats.” It’s also an important season, considering it was the first in HD. But none of its other great episodes have the scene where Dennis explains to Mac what “the implication” is, and that alone is more than enough to net “The Gang Buys a Boat” the title of best episode of Season 6.

5) “The Gang Gets Trapped” (Season 7, Episode 9)

Like Season 2 and Season 5, Season 7 is one of Sunny‘s best. A big factor in its success is undoubtedly the fact that the ultra-talented Matt Shakman directed every last one of its 13 episodes. You might recognize Shakman as the director of episodes from even bigger shows like Game of Thrones, Succession, Monarch: Legacy of Monsters, or every installment of WandaVision (not to mention the upcoming The Fantastic Four: First Steps).

“Frank’s Pretty Woman,” “Frank Reynolds’ Little Beauties,” “Chardee MacDennis: The Game of Games,” “How Mac Got Fat,” they all rank up there with the series’ best. But “The Gang Gets Trapped” is even more so. After seven years, the gang was ready to get introspective, and this episode is the ultimate in having them point out one another’s specific, grating flaws. All while inside a closet in the suburban home of some (supposed) southerners who they fear will tie them up to two horses and have those horses run in opposite directions.

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6) “Mac Day” (Season 9, Episode 5)

If there’s any season where there are A-level episodes and swings-and-misses with not much in between, it’s Season 9. On the A-level side of things there was “The Gang Tries Desperately to Win an Award,” “The Gang Gets Quarantined,” and “Mac Day.”

Everything about “Mac Day” is hysterical. Mac is a needy guy to begin with, so when the day that’s supposed to be devoted to him instead ends up being dominated by his cousin, “Country Mac,” (American Pie‘s Seann William Scott) his increasing despair is only increasingly engrossing. Not to mention, the final scene teasing the beginning of Frank Day is an all-timer.

7) “The Gang Beats Boggs” (Season 10, Episode 1)

A big part of Sunny‘s appeal is the gang’s tendency to get absolutely hammered. It’s really all they do. Drink and squabble, squabble and drink. So, to see them do that on a packed aircraft thousands of feet in the air is a winning concept (though it didn’t really work when the show tried it a second time).

There are a few great moments in the episode. For instance, the two mentions of Executive Decision and Passenger 57, Dee’s consistent failure to grasp who Wade Boggs is, Charlie’s failure to grasp that the man is alive, and Dennis’ hastily assembled (and totally wrong) summarization of the most attractive woman on the plane.

8) “Mac & Dennis Move to the Suburbs” (Season 11, Episode 5)

Always Sunny has always benefited from perfectly-cast side characters (including the late Lynne Marie Stewart as Charlie’s Mom), but the true appeal is seeing Mac, Charlie, Dennis, Dee, and Frank spar with one another. In fact, the characters are so well drawn that a 22-minute episode can not only survive, but thrive, even when its focus is just on two of the core five.

For instance, “Mac & Dennis Move to the Suburbs”, which has, well, Mac and Dennis move out of their inner-city Philadelphia comfort zone into the surrounding suburban area. Now they’re forced to just deal with one another. The end result? Lots of “Mac’s famous Mac ‘n Cheese” (really just boxed mac ‘n cheese), a dead dog, and Dennis pretending he doesn’t hear the smoke alarm beep that’s driving Mac figuratively crazy (and Dennis literally crazy).

9) “Hero or Hate Crime?” (Season 12, Episode 6)

Like the next episode on this list, “Hero or Hate Crime?” displays just how effective Sunny is when it shows the characters in a panel setting. They’re lined up in a single location and forced to confront both themselves and their own flaws.

But “Hero or Hate Crime?” has the edge over the next entry and Season 14’s “Thunder Gun 4: Maximum Cool” not because it was first, but because it was really the show analyzing its own progressive evolution. What is still acceptable now vs. what had been unacceptable once, and perhaps how we should consider things in the future.

10) “Time’s Up for the Gang” (Season 13, Episode 4)

There’s no way to make a show about bad behavior that survives the dawn of the “Me Too” era without eventually acknowledging that era. And the way Sunny went about that was absolutely brilliant. The gang is brought to a conference focusing on improving the practices of Philly’s worst bars, a list on which Paddy’s most certainly finds itself (though the whole conference ends up being a ruse). It’s a great hook to get the gang in one location so each member can be forced to acknowledge their past sketchy actions. Things kick off in a hilarious way, with Dee coming into the room excitedly chanting “Time’s Up, Time’s Up, Time’s Up!” with a soda in hand, immediately after Dennis asks who could possibly be having a good time in this scenario.

At the end of Season 12, it sure did seem like Dennis actor Clenn Howerton was being written off the show. He had A.P. Bio to occupy a substantial chunk of his time, and fans wondered how the gang could go on without its most sociopathic member. The answer was it didn’t really have to. Much of Season 13 features Howerton and even in the episodes where he’s absent, there’s so much going on it’s not glaringly obvious. And, by next season, he was back in full. Along with “Time’s Up,” three of the season’s best have Howerton, including “The Gang Escapes” and “The Gang Solves the Bathroom Problem,” and two do not (“Charlie’s Home Alone,” and “Mac Finds His Pride).”

It’s Always Sunny In Philadelphia is streaming on FX-Hulu.