The 15 Funniest Episodes of It's Always Sunny in Philadelphia

I'll say it. I'm basically an awful human being. And as an awful human being, I love that paean to sociopathy, It's Always Sunny in Philadelphia. True, I'm from Philly, and I'm fairly certain they used my friend's apartment building for the exterior shot of Dee's apartment, but that's neither here nor there. I love the show because it's hilarious and mean.

But when I sat down to pick the 15 funniest episodes, I ran into a problem. In rewatching the series, I realized that something like 90% (conservative estimate) of the episodes are amazing. So these are MY top 15. You might pick a totally different bunch. So if you think I'm wrong (and yes, I know I left Pepe Silvia and can wine AND Charlie going America all over everyone's asses off the list), argue with me. It'd only be in the spirit of the show, after all. Worst case scenario, I'll be relegated to Charlie work.

 

15. The Gang Recycles Their Trash
Season 8, Episode 2
Sunny skewers its characters on a regular basis, but it's the meta-skewering in this episode that vaults it into the top 15. And when the sanitation workers of Philadelphia go on strike, why shouldn't the gang retry failed schemes of the past (from selling a service door-to-door to running billboards) and see them kind of succeed for once? In an otherwise lackluster season, "The Gang Recycles Their Trash" seems to acknowledge that the show's best days may be behind it, but at least it's not going to pretend it doesn't know that.

 

14. Thunder Gun Express
Season 7, Episode 11
This one clearly takes inspiration from the episode of Seinfeld where that foursome tried (and mostly failed) to meet up for a movie. But as misanthropic as that show was, this one — that has the gang running around Philadelphia, ditching one another when it becomes convenient, and... uh... hijacking a boat full of tourists — probably beats out that nihilistic masterpiece. Bonus creepy points go to Dennis listening to his self-recorded sex tapes in the car.

 

13. The Gang Makes Lethal Weapon 6
Season 9, Episode 9
With the blackface vs. blackvoice argument a thing of the past, "Lethal Weapon 6" is pure fan service. There's barely a framing story here and what little does exist is just an excuse to build on season 6's "Dee Reynolds: Shaping America's Youth" and show more of the gang's demented take on the Lethal Weapon franchise. Yes, Mac and Dennis switch characters halfway through and Frank gets his creepy sex scene featured, but it's the homoerotic locker room scene where Mac's latent urges for Dennis take center stage that steals the show.

 

12. Mac and Dennis Break Up
Season 5, Episode 9
A throwaway insult from Dee causes Mac and Dennis to question if they're not just a little too dependent on each other, causing a game of musical apartments. Mac attempts to spend time with Charlie and Frank, which causes Charlie to head over to Dee's, etc. Dee attempts to right her wrong by luring the roommates to dinner with the promise of "large breasted women" — who, of course, fail to arrive — and the boys are once again best friends. As Sunny goes, this is as low key as it gets, but even it's smaller, sweeter premise leads to some ace Charlie lines, including the iconic "Cats do not abide by the laws of nature."

 

11. Charlie Gets Molested
Season 1, Episode 7
You'd think that even a show whose pilot was called "The Gang Gets Racist" would draw the line at making fun of child abuse. You would be wrong. The first season ends with this supremely warped (and, well, hilarious) episode in which we meet both the disgustingly greasy and opportunistic McPoyle brothers and Charlie's perverted, pedophilia-inclined Uncle Jack. In playing Charlie's potential childhood molestation (at the hands of a gym teacher) for laughs, we were given the first brutally honest glimpse of what we'd be in for in the following seasons, a mentality exemplified in this exchange:

Charlie: OK, OK. First of all, there are people out there who actually have been molested and you guys are going to exploit that for your own personal gain? You assholes are securing your places in hell.

Ryan McPoyle: We've thought about it. We're willing to roll the dice.

 

10. The Gang Saves the Day
Season 9, Episode 6
How would you react if you were in a convenience store being held up? If you'd use the situation to your own advantage — whether that's to showcase your karate skills, become a famous actress (don't ask), or marry the woman of your dreams — congratulations, you'd fit right in with the gang. Really, the episode is in pretty strong territory up until the last segment: Charlie's dream, a note-perfect homage to Up, where his fondest dream is not to travel to Paradise Falls, but instead to purchase bushels of janitor and waitress children at the "Baby Store," and bury his beloved wife next to his equally beloved rats. It's sweet and sad and hysterical all at the same time.

 

9. The Gang Gets a New Member
Season 6, Episode 8
Group cohesion is a fragile thing. Introduce a rogue element, and it could all come crashing down. The rogue element in this case being Jason Sudeikis as a former member of the gang. Previously (and poetically) ejected from the group by being pushed out of a moving car, this time he's back and better than Charlie at just about everything — butt dance included — except deferring to Mac and Dennis. The decision is clear: ejection by vehicle, part deux. On the upside, Mac is now free to eat fries, despite Dennis's fatwa on the action.

 

8. Paddy's Pub: Home of the Original Kitten Mittens
Season 5, Episode 8
Just gonna leave this here: Hello, Charlie Kelly here, local business owner and cat enthusiast. Is your cat making too much noise all the time? Is your cat constantly stomping around driving you crazy? Is your cat clawing at your furniture? Think there’s no answer? You’re so stupid! There is! Kitten Mittens. Finally, there is an elegant, comfortable mitten for cats…. I couldn’t hear anything! Is your cat one-legged? Is your cat fat, skinny, or an in-between? That doesn’t matter! Cause one size fits all! Kitten Mittens! You’ll be smitten!

 

7. Mac Fights Gay Marriage
Season 6, Episode 1
Mac's biblical convictions (and his willingness to abandon them) have always been a big part of Sunny, but never moreso than when he attempts to justify his rejection by a transwoman whom he'd bedded before her final surgery. Incensed that she's now free to marry someone he deems subpar, he embarks on a one-man crusade — all the time ignoring Charlie and Frank's impending tax-related (and possibly incestuous) nuptials. I guess the Bible only applies to hot chicks.

 

6. The World Series Defense
Season 5, Episode 6
OK, let me level with you: This was the first Sunny episode I ever watched — and it was only because of its Phillies connection. I watched it at work (hiyo!) and then I immediately watched it again. And thus a love story was born! Truthfully, Sunny doesn't acknowledge its hometown often enough for my taste, but this is a terrifically funny tribute to Philadelphia and its fairly insane fans. It's also the genesis of Mac's sticker-laden love letter to Chase Utley, which is a tour de force of epistolary storytelling in its own right.

 

5. The Gang Gives Back
Season 2, Episode 6
We're in the homestretch here, so we're getting to the really disturbing essence of the the gang. Blow up a building in the name of fake jihad and what's your sentence? Apparently in Philadelphia, it's to work with underprivileged youth in a rec basketball league. Yikes. Of course (of course!) the gang splits up and teaches the kids to fight dirty, complete with shoving tacks into opponents. But it's Charlie's discovery of the Waitress in his court-ordered AA session that really cultivates the seeds of her hatred sown in the next episode on our list.

 

4. Mac Bangs Dennis' Mom
Season 2, Episode 4
There are no real winners in this episode, but there are two clear losers: Charlie and the Waitress. In using his knowledge of Mac's indiscretion with the twins' mother to manipulate the rest of the gang for his own purposes, he inadevertenly causes the object of his affection to sleep with... Frank. She, of course, only sleeps with him in order to get back at Dennis, who'd been playing his own game with Charlie. Charlie is shattered. The Waitress is shattered. But us? We laugh. Because we're all actually terrible people.

 

3. Dee's Dating a Retarded Person
Season 3, Episode 9
Dennis might actually be the worst person in the gang. The others all have their own issues, but he likes to manipulate them for the fun of it. He's basically a psychopath. Case in point: this episode. Dennis convinces his sister that the up-and-coming rapper she's dating suffers from mental retardation (a term that I, quite frankly, don't even feel comfortable writing). He even accompanies her to the boyfriend's house (he lives with his mom) and so colors her opinion of him that she feels forced to dump him based on suspicion alone. But really, the main storyline here is less important than what gets introduced in this episode, namely, The Nightman. More on that in a second.

 

2. The Waitress is Getting Married
Season 5, Episode 5
Sunny is at its best when it functions as a showcase for Charlie's incomprehensible tendencies, which is why the last two entries on this list are what they are. The gang, worried for Charlie (aw) when they find out the Waitress is engaged, set out to find their put-upon friend a match. I'm not sure any description can do justice to this episode, all I can do is quote Charlie, trying to explain that he's a philanthropist: "I'm a full-on rapist! You know: Africans, dyslexics, children. That sorta thing."

 

1. The Nightman Cometh
Season 4, Episode 13
And here we are, the episode so amazing, they took it on the road and toured with it. A send-up of musicals, romance, and the show itself, The Nightman Cometh is one of the funniest half-hours that has ever aired on television. Kudos especially to the fearless Charlie Day, who's never been better, and is clearly having the time of his life. Get this man a Broadway show, stat.


Bonus Pepe Silvia:

Leah E. Friedman is the editor of SideReel.com. She's from Philadelphia and she's a terrible person, but the two aren't related. If you know where to get a Wawa hoagie in San Francisco, she's all ears. You can follow her musings on Twitter

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