Funniest It’s Always Sunny In Philadelphia Episodes, Ranked

Inspired by Extreme Home Makeover, the Gang wonders, “What would Ty Pennington do?” Attempting to do something good, the Juarez family that just moved in down the street is selected for an extreme makeover. In the classic, It’s Always Sunny In Philadelphia fashion, no one knows what they’re doing, starting with the terrifying home break-in and ending with the complete destruction of the home.

As the makeover spirals further into insanity, Charlie ends up trying to make a taco bed, while Frank wants to screen Apocalypto about how their ancestors were savages “until Mel Gibson and the Catholics saved them.” Retta, from Parks and Recreation, makes a brief cameo as the hardware store clerk that has no idea what the Extreme Home Makeover account is.

“The D.E.N.N.I.S. System” isn’t the first Always Sunny episode that proves Dennis is a sociopath, but it’s the best. Dennis explains every step using his seduction of Caylee, a pharmacist played by Glenn Howerton’s real wife, Jill Latiano, but he’s disgusted over how Mac and Frank have developed their own systems based on his cast-offs.

The level of cringe humor crammed into the 22-minute episode out does The Office, but as usual, what makes it hysterical is how insane the Gang becomes, and the rest of the world is aware of this, with the appropriate reactions. “The D.E.N.N.I.S. System” is almost as horrible as the implication conversation, and as usual, everyone else but the Gang wins in the end.

Since Always Sunny excels when the Gang runs up against normal people, “The Gang Dines Out” is a classic by pitting them against a fancy restaurant and a poor, beleaguered waiter (Michael Naughton). Guigino becomes the setting for a series of “ones-ups-manship,” from pouring out wine to asking the waiter to tie shoelaces together, before finally uniting the group together as the horrible friends that they truly are.

There are so many great moments in this episode, it’s hard to pick just one, from Dee trying to get the waiter to sit with her to Frank’s hairpiece (one of the many that Danny DeVito wears, and it’s always funny), and finally, Dennis’ “double jack knife twist.”

Ironically, the Gang’s behavior is never worse than when they are trying to actively not be horrible people. “Mac and Dennis Move to the Suburbs” takes Always Sunny out of Philadelphia, where Mac and Dennis can’t find an affordable apartment, and bet Frank that they’ll last more than a month in the suburbs. The lack of bars, a barking dog, and their incredibly friendly neighbor Wally bring out the worst parts of Mac and Dennis.

Playing off the usual suburban cliches, as most normal sitcoms do on a weekly basis, isn’t the strength of Always Sunny, but that’s why it’s a brilliant one-off episode. Pay attention to the growing pile of trash inside their house, one of many subtle gags about how Mac and Dennis have no idea how life works outside of the city.

The Gang’s dynamic is defined in this episode, Mac’s the brains, Dennis’s the looks, and Charlie’s the wild card, as they embark on another scheme to get rich quick. Using a bank loan, they want to buy gas, store it in the basement of Paddy’s, and sell it a year later for profit. It’s no surprise that the situation devolves, but when they decide to sell it curbside and light fireballs to attract motorists, well, it’s a new low for the Gang.

The best bit, though, is the sad fate of the gold car, which Dee runs into twice in the episode, and then, when Charlie embraces being the “wild card,” it all gets worse. Framing Dennis and Dee’s dad for supporting terrorism is ridiculous, yet it’s overshadowed by, well…just look at that image again.

After saving old photos of their trips to the Jersey shore, Dennis and Dee suggest everyone goes to the beach while they re-create their old vacations. In order this results in catching homeless men under the boardwalk, hair getting stuck in a Slingshot ride, smoking drugs, getting caught up in a robbery, digging a grave, and dodging bullets. It’s a jam-packed episode since that only happens to Dennis and Dee, while Frank and Mac are caught on a raft drifting out into the ocean before getting saved by a boat of Guidos.

Notably, this is the second time Charlie has left Philly in his life, and during an encounter with The Waitress on the beach, she admits to using ecstasy, marking the start of her slow descent into being an even worse person than the Gang.

Even during the episode, the Gang debates using the “R” word, but given that Dee’s new boyfriend is an up-and-coming rapper that doesn’t drive, likes juice boxes, and lives at home, all of them are convinced he’s retarded. Yet they agree to have him perform at the bar for some say publicity, which causes the guys to form a band, since if Dee’s boyfriend can perform and get laid, they can too.

What happens is one of the greatest bits in the history of Always Sunny, as Charlie writes a rock opera and Dennis is excited to perform and be hailed as a “rock god.” This was the world’s introduction to Nightman, a joke that paid off later in an even better episode. Oh, and Dee’s boyfriend isn’t, but this episode is all about “Day Man, fighter of the Night Man.”

First off, this episode aired in 2013 and centers around the flu running rampant in Philly, but Always Sunny nailed the madness that overcame most of the population in 2020 during the Covid pandemic. Frank, panicking over the flu, forces everyone to stay in Paddy’s Pub, forcing anyone who shows signs of being sick into the bathroom. Naturally, this leads to a Danny DeVito Apocalypse Now parody and ends with Frank completely hairless and covered in hand sanitizer.

This time, it’s all about the Gang’s personalities running up against each other, and the results are always hysterical. The fact they predicted some of the insanity from the later real-life quarantine, from suiting up to go out in public to arguments over getting food delivered, makes this episode even better in retrospect.

A parody of Family Feud that even goes so far as to poke fun at contestants giving double-entendre responses, “The Gang Goes On Family Fight” is Always Sunny at its best. Keagan-Michael Key, as a parody of Steve Harvey, is perfect, giving the greatest facial expressions to the insane responses, including Charlie stating that humans eat dragons. In each round, Charlie gives an insane answer and gets exactly one point, leading up to the punchline that he took the survey at the mall.

Left forever unanswered from this episode, for the best, is how Frank watched “many pigs eat many men,” but there are a ton of deep-cut jokes in the responses, from laser-removing hair to the toe knife. Most of the best episodes have one thing in common though, and that’s, again, Nightman, which gets an absurd shoutout in this episode.

“The Nightman Cometh” is not only the greatest episode of Always Sunny but one of the best sitcom episodes in history. Charlie staging a rock opera based on the song from “Sweet Dee’s Dating A Retarded Person,” but now it’s been expanded with horrible, yet amazing, results. This time, Danny DeVito is added as a troll, singing classic lines that rhyme “hole” with “toll” and should not be repeated in public, with Dee joining in as the Princess that falls in love with Day Man.

The joke is that it’s a horrible musical, but the Gang performs it so earnestly that it becomes the pinnacle of cringe entertainment. And all of that is before Charlie descends from above the stage and proposes to the Waitress, with predictable results.

Amazingly, the cast turned this episode into an actual stage show, going on a multi-city tour to perform the real musical. Fans have even used their own versions of the musical to launch proposals, which is an amazing legacy for the funniest episode in Always Sunny history.