Read update
It is hard to go wrong with any episode you choose ofIt’s Always Sunny in Philadelphia. It’s the longest-running live-action sitcom for a reason, though it leans hard into dark humor and generally requires every trigger warning on the book before you settle in.
With Season 15 wrapped as of December 2021 and the show renewed at least up until Season 18, there’s no time like the present to look back over some of the episodes that make it great.
Updated on June 12, 2025, by Hannah Saab:
With Season 16 ofIt’s Always Sunny in Philadelphiafinally here, it’s the perfect time to binge-watch the most rewatchable episodes while waiting for new ones every week.
10"Mac and Dennis Buy a Timeshare"
Season 9, Episode 4 (2013)
What makes the episode sofunny is how relatable it is to people who are accustomed to seeing vacation scams play out in real-time. It is a fun episode to watch before going on a vacation that doubles as a cautionary tale.
Almost everyone has had people try to sell them pyramid scheme products like vitamins, filtered water, cosmetics, the latest hot fad, etc. If not one of those scams, then timeshares. Timeshare salespeople usually approach people when they are relaxed and on vacation. ThehilariousAlways Sunnyepisodehas both of those types of scams and more.
9"Time’s Up for the Gang"
Season 13, Episode 4 (2018)
Paddy’s Pub has been put on a list that claims the bar has been sexually hostile toward women. The gang must attend a sexual harassment seminar to get off the list. This episode is rewatchable because it is like holding up a mirror to the worst parts of society.
This episode confirms a lot of what viewers have been aware of since day one while also exploring some uncomfortable subjects through humor. Still, It’sAlways Sunny in Philadelphiais known for poking fun at taboo subjects, and they do it exceedingly well in this rewatchable episode.
8"The Gang Reignites the Rivalry"
Season 5, Episode 12 (2009)
Kicking off with Frank Reynolds (Danny DeVito) talking about how sexy he looks in skinny jeans, those silly, feeling-yourself vibes are what ultimately define this episode.
The episode (in one of thebest seasons ofIASIP) is about Paddy’s Pub being banned from a local drinking competition called Flipadelphia. The ban has been lifted, and the gang can compete again. The competition is about flipping cups while drunk. It ends up going in a ridiculous direction at a frat house, which will make you belly laugh.
7"The Gang Buys a Boat"
Season 6, Episode 3 (2010)
“The Gang Buys a Boat” is a fan-favorite episode because Charlie’s (Charlie Day) idea of a great boat differs from Mac and Dennis’s idea, and the fallout grows to epic proportions (as usual).
Mac and Dennis are thinking more of a party boat, and Charlie wants a shrimp boat likeForrest Gump. So while Charlie is extremely disappointed by what’s happening, Mac and Dennis attempt to live the “high life” by socializing with fellow boat owners – it does not go well. Sweet Dee’s (Kaitlin Olson) goofy boat dance is the icing on the messed-up cake.
6"The Gang Goes to Hell"
Season 11, Episode 9 (2016)
Mac (Rob McElhenney) wins a Christian cruise in a church raffle. He convinces the gang to go on the cruise with him. The episode makes fun of Mac’s decision to embrace Christianity despite the fact that he is, at heart, a bad person (just like every member of theIt’s Always Sunnygang is awful).
Another focal point is the intersection of Mac’s faith and his sexual orientation and gender identity, which are topics that other sitcoms have dealt with, but usually not in the same episode. All this and more is what makes this a strangely profound, but still hilarious episode as the gang attempts to defend their ultimately terrible behavior.
5"The Gang Goes to the Jersey Shore"
Season 7, Episode 2 (2011)
Sweet Dee and Dennis take the gang to their favorite childhood vacation spot; unfortunately, the Jersey Shore isn’t the paradise that Sweet Dee and Dennis remember.
This turn of events is bad for them but great for the viewers because the episode is full of belly laughs. The Rum Ham is so profoundly ridiculous it is hard not to laugh. Charlie’s confusing night with the Waitress is also fun to watch over and over again, as her reaction after waking up next to him on the beach is both funny and sad.
4"Thunder Gun Express"
Season 7, Episode 11 (2011)
The gang wants to see the hottest action film in town, but it is going to take a lot of effort to get there. The experience will ring true for anyone who has tried to plan a group outing.
The gang is split up, and the episode crosscuts between the lengths and efforts each gang member will go through to see an action movie with hilarious rewatchable laughs. TheIASIPepisode is full of ridiculous momentsthat highlight how wacky each character is.
3"The Gang Goes to a Water Park"
Season 12, Episode 2 (2017)
When “The Gang Goes to a Water Park,” fans can expect hilarious hijinks. In one of the most unforgettable episodes from recent seasons, viewers see the group totally terrify a bunch of kids as Mac’s laminated entry bracelet gets stuck in a water slide. Frank and Charlie have a painful time. And Dennis meets a kid who’s just like him (and maybe even better).
The episode uses the classic formula of showing each character’s gut-busting weakness, while also reminding fans that they have no sense of shame in public. It’s a disaster from start to finish, and when viewers think it can’t get any worse, it somehow does – this perfectly captures the essence of the show.
2"The Night Man Cometh"
Season 4, Episode 13 (2008)
Among the most quoted TV episodes of all time, this infinitely rewatchable episode is surprisingly relatable. Most people either know someone in community theater or have been in community theater, or at the very least, know someone who has or has tried to do something creative and failed miserably at it – this makes themusicalAlways Sunnyepisodeespecially funny.
The play, of course, is ridiculous but hilarious. Even though it’s all extremely absurd, you’ll find yourself humming these surprisingly catchy songs to yourself for years to come. Charlie’s cringe-worthy reveal at the end is also a fantastic scene to see more than once for viewers who love that type of humor.
1"McPoyle vs. Ponderosa: The Trial of the Century"
Season 11, Episode 7 (2016)
Prepare for multiple laughs with this episode. It’s the funniest episode ofIt’s Always Sunny in Philadelphia,and that is saying a lot for a series that has made fans laugh out loud more times than they can count.
What makes the episode so great is that it’s a spotlight for some of the viewers' favorite recurring characters. They are all together in court and doing their best to be silly and up to their usual misdeeds. However, be warned – watching the episode may inspire you to go out and get a degree in bird law.
