How does a live-action comedy attain longevity without going stale in the process? It’s Always Sunny in Philadelphia has been on the air for almost 15 years, initially premiering in August of 2005. The series has maintained its standard of excellence for 14 seasons, never wavering in its ability to deliver laughs and gasps alike. Not to mention, It’s Always Sunny in Philadelphia doesn’t shy away from tackling hot-button topics. Whether it’s an episode where the gang discusses racism or which terms are considered politically correct, this show pushes boundaries without fear. Nothing is too taboo or off limits. Of course, it should be noted that It’s Always Sunny in Philadelphia pokes fun at the arrogant and self-obsessed characters on the show. But, it’s still rooted in honesty, and that’s where the comedy shines. 

Below, I’ve compiled a list of my top 20 favorite episodes of It’s Always Sunny in Philadelphia. This list was painstakingly difficult, seeing as every episode is laugh-out-loud funny and cleverly written. But, I shouldered the overwhelming task with aplomb, because that’s what real heroes do…from the comfort of their own couch. 

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“Mac Finds His Pride” (S13E10)

Now, I feel like this episode’s reception was a mixed bag. Some decried it for not being particularly funny, while others hailed it as revolutionary. I agree with the latter – “Mac Finds His Pride” was a poignant love letter to the LGBTQIA+ community. Watching Mac (Rob McElhenney) come out to his father via dance routine was altogether heartbreaking and beautiful. Frank (Danny DeVito) noticeably weeping at the end and finally understanding/supporting Mac was so wonderful to watch. Who knew It’s Always Sunny in Philadelphia could make me cry (and not from laughing)?

“Dennis and Mac Move to the Suburbs” (S11E05)

Mac and Dennis (Glenn Howerton) falling prey to the monotony of the suburbs felt all too relatable. Not to mention, Dennis unraveling and unleashing his fury upon his poor neighbor Wally was gut-busting funny. Their domestic dynamic is intriguing. Mac plays the “housewife” while Dennis is the “breadwinner” of the two. This episode dissected the suburban family trope with hilarious results. Remind me to never move in with Mac and Dennis. 

“The Nightman Cometh” (S04E13)

“Don’t say ‘stage freeze,’ just do it!” Charlie (Charlie Day) pens a musical to reel in the girl of his dreams – the Waitress (Mary Elizabeth Ellis). Oh, and fun fact: Charlie and the Waitress are happily married in real life. Anyway, the Waitress isn’t impressed with Charlie’s magnum opus, and insists on embellishing that restraining order. The musical, “The Nightman Cometh,” is a classic Sunny staple. If I actually had to rank these episodes, I’d put this one in my top five. Charlie making Dennis and Dee (Kaitlin Olson), who are twins, a romantic couple definitely tickled my funny bone. Well, more like their reaction to the aforementioned. 

Still of Rob McElhenney, Charlie Day, Glenn Howerton, Kaitlin Olson and Danny DeVito in It's Always Sunny in Philadelphia

IT’S ALWAYS SUNNY IN PHILADELPHIA — Pictured: (L-R) Rob McElhenney as Mac, Charlie Day as Charlie Kelly, Glenn Howerton as Dennis Reynolds, Kaitlin Olson as Dee Reynolds, Danny DeVito as Frank Reynolds. CR: Patrick McElhenney/FX

“Charlie Work” (S10E04)

Who doesn’t love doing Charlie Work? “Charlie Work” is an homage to Birdman Or (The Unexpected Virtue of Ignorance). We see Charlie scrambling to ensure Paddy’s Pub receives a stellar mark when the Health Department pays the gang a visit. Charlie leads the health inspector around the bar in one continuous shot as percussive beats punctuate his movements in the background. Why Charlie Day was never nominated for an award for this episode, I’ll never know.

“Dennis and Dee Go on Welfare” (S02E03)

This one is an oldie but a goodie. Dennis and Dee try to cheat the welfare system while in pursuit of their actual dreams – veterinarian and actress, respectively. Then, they decide that being under the influence of drugs would get them more money from the government. Of course, the sibling pair wind up addicted to crack in the process and accomplish nothing. Guess there’s always a surefire career at Paddy’s Pub!

“The Gang Gives Frank an Intervention” (S05E04)

Adding Danny DeVito to the cast in Season 2 was easily one of the best decisions the Powers That Be ever made. DeVito is uninhibited, so naturally a role like Frank Reynolds gives him room to wreck havoc as only he can. This episode finds the crew staging an intervention on Frank over his descent into madness and depravity. However, Frank mistakes this as a comedy roast, which makes it all the funnier. 

“CharDee MacDennis: The Game of Games” (S07E07)

Now, who doesn’t love a good drinking game? “CharDee MacDennis: The Game of Games” combines every known tabletop game into one. But, don’t try this game at home, folks. Not unless you want to destroy your liver and possibly sustain multiple bodily injuries. 

“The Gang Gets Analyzed” (S08E05)

My heart goes out to the therapist that attempted to pick apart the brains of these Jabronis. Dee brings the gang to one of her therapy sessions. She forces her therapist to decide who [in the gang] should wash the dishes after their dinner party. Naturally, Dennis inserts himself into each person’s individual session with the therapist. He claims to possess heavily detailed records of everyone on hand. That’s normal. Speaking of normal, the therapist deems Charlie the most levelheaded of the bunch. You know, the man who kills rats, eats cat food and wanders through the sewers for fun.

“The Gang Goes on Family Fight” (S10E08)

Keegan-Michael Key guest stars in this episode as a game show host for Family Fight. Key does a terrific job of playing the “straight character” to the gang’s wacky personas. Frank turns out to get every answer right, Charlie believes that not enough people eat dragons, and Dee brings a fart button for laughs. In addition, Dennis has a breakdown on national TV and it’s downright hysterical. Howerton is an underrated actor, and I’ll continue to say that until someone recognizes him for his immense acting prowess. 

“Hero or Hate Crime?” (S12E06)

Now, It’s Always Sunny in Philadelphia is at its best when the gang can just riff on sensitive issues. Their warped sense of morality and blatant unawareness never fails to make me giggle. In this episode, they ponder over whether Frank shouting “f*g” at Mac constitutes as a hate crime. However, Frank addressed Mac as such to save him from death by falling piano. So, does that make him a hero? In typical Sunny fashion, the gang hires an arbitrator to help them sort out this mess. And in four hours, no less! That’s a record for them!

Still of Rob McElhenney, Danny DeVito, Glenn Howerton, Kaitlin Olson and Charlie Day in It's Always Sunny in Philadelphia

IT’S ALWAYS SUNNY IN PHILADELPHIA — Pictured: (l-r) Rob McElhenney as Mac, Danny DeVito as Frank, Glenn Howerton as Dennis, Kaitlin Olson as Dee, Charlie Day as Charlie. CR: Patrick McElhenney/FX

“Hundred Dollar Baby” (S02E05)

Of course, this is a play on Million Dollar BabyFrank decides to train Dee in the art of boxing when an old rival challenges him to a stint in the ring. In the B story, Dennis and Mac enlist Charlie to fight in the underground fighting circuit. Both Dee and Charlie get hopped up on steroids, and the results are side-splitting funny. I can’t imagine Kaitlin Olson and Charlie Day held it together without at least one slip-up during those “rage” scenes. 

“The Gang Turns Black” (S12E01)

Now, this episode came about when Black Lives Matter surged to the societal forefront. This is another Sunny installment with mixed reviews. I think it’s brilliant. These characters have struggled with their collective racism throughout the course of the show. “The Gang Turns Black” finds the gang electrocuted during a storm. The following day, they discover their reflections in the mirror are completely different people. Thus, they set out into the world to fix the problem. Along the way, they learn what people of color encounter in their day-to-day lives. This episode does a tasteful job of pulling back the curtain on this issue without resorting to blackface. On top of that, it was a musical episode. Howerton is quite the gifted vocalist, and I need to see him in a musical someday. 

“The Gang Goes to a Water Park” (S12E02)

This episode was chock full of hi-jinks and debauchery – Sunny style. Besides its clever writing, It’s Always Sunny in Philadelphia is adept when it comes to delivering pitch perfect slapstick comedy. As far as I’m concerned, Kaitlin Olson is a modern-day Lucille Ball. Dennis connects with a girl on a genuine, emotional level, counteracting his typical psychopathic tendencies. Charlie and Frank pretend the latter is gravely ill so they can barge to the front of the line for water park rides. It’s just a solid and funny episode. 

“Sweet Dee’s Dating a Retarded Person” (S03E09)

Reminder – this episode aired in 2007, so the aforementioned title may come off as a little too coarse. However, as per their usual, It’s Always Sunny in Philadelphia is proving a point: never judge a book by its cover. Also, the gang is the absolute worst. This episode birthed the song “Dayman,” (as performed in “The Nightman Cometh” episode) which may be one of the most prolific masterpieces of our time. He really is a master of karate and friendship for everyone!

Still of Danny DeVito, Kaitlin Olson, Glenn Howerton and Rob McElhenney in It's Always Sunny in Philadelphia

IT’S ALWAYS SUNNY IN PHILADELPHIA — Pictured: (l-r) Danny DeVito as Frank, Kaitlin Olson as Dee, Glenn Howerton as Dennis, Rob McElhenney as Mac. CR: Patrick McElhenney/FX

“Mac and Charlie Die Pt. 1 and 2” (S04E05 and S04E06)

This two-part episode marks the first time I ever watched It’s Always Sunny in Philadelphia back in 2008. It’s hard to believe that the aforementioned aired 12 years ago. Anyway, Mac and Charlie decide to fake their own deaths after the former’s dad is released from prison. They’re convinced Mac’s dad is out to kill them, but really his father wants to get as far away from them as possible. Dennis, Frank and Dee hold a funeral for the pair in the bar, with only Mac’s mom and Charlie’s mom in attendance. Eventually, they discover that Charlie and Mac are alive. You know, since the pair are crawling through air vents while speaking at full volume. In addition, this episode has one of my favorite Dee scenes: her riding public transit. It’s gold. 

“The D.E.N.N.I.S. System” (S05E10)

Is it narcissistic to have an intricate system for bedding girls that’s named after yourself? Well, according to Dennis Reynolds, it’s not. But we know better. “The D.E.N.N.I.S. System” is absurdity at its finest. Not to mention, there’s a cameo by Howerton’s real-life wife Jill Latiano. She portrays the woman Dennis is aiming to bed. Another fun Sunny fact: Kaitlin Olson and Rob McElhenney are married in real life, which makes their disdain for each other on the show even funnier. This series is a family affair, folks. 

“Thunder Gun Express” (S07E11)

The gang is hellbent on making it to a showing of the fictitious Thunder Gun Express, your stereotypical “dude bro” movie. We see the crew, one by one, inevitably abandon each other amid their race to the theater. It all plays out like an over-dramatic action flick, presumably akin to the fake film in this episode. Highlight: Frank giving an impromptu riverboat tour after he overthrows the actual tour guide. 

“The Gang Solves the Gas Crisis” (S04E02)

Now, this episode aired in 2008 during the gas crisis that plagued the nation. You remember that time when gas was exorbitantly expensive? The gang tries to alleviate said gas crisis, but crashes and burns spectacularly in the process. Literally. “The Gang Solves the Gas Crisis” is another classic Sunny installment. In fact, Season 4 as a whole really is some of their best work. 

“The Gang Gets Held Hostage” (S03E04)

Did you know that, prior to starring as a hunk in Westworld, Jimmi Simpson portrayed one half of the McPoyle brothers on Sunny? The McPoyle family is notorious for never breeding outside their own bloodline. They’re incestuous and just downright creepy, with a strange love for milk. We see the McPolye brothers and their sister overtake Paddy’s Pub as they hold the gang hostage. Dee eventually succumbs to Stockholm Syndrome, while Frank is in the air vents searching for his will. The McPoyle trio force the gang to strip to their undies and destroy the bar. There’s oodles and oodles of betrayal and backstabbing. This is Sunny at its finest: absurdist, fast-paced and loud.

“America’s Next Top Paddy’s Billboard Model Contest” (S04E03)

My favorite line from this episode is spoken by Frank: “Dennis, your mule is sh*t. I’m no longer turned on by mules.” This line cracks me up every time I watch this episode. Frank reveals that he paid for a billboard to showcase Paddy’s Pub and, hopefully, attract more patrons. The gang decides to hold a modelling contest to rein in an attractive man and woman for said billboard. Naturally, things go awry when Dennis’ vanity must be sated, so he enters himself into the contest. Dee and Charlie set out to become internet famous. Mac holds a Bachelor-like competition to find his next girlfriend. Overall, this episode ticks off the right boxes for me. 

Honorable Mentions: “The Gang Tries Desperately to Win an Award” (S09E03) and “The Janitor Always Mops Twice” (S14E06)

“The Gang Tries Desperately to Win an Award” has a wonderful music performance by Charlie Day. Paddy’s Pub undergoes a revamping as the gang takes a more amiable approach to how they treat customers. The result is Charlie spitting on people and the core characters realizing that they’re, well, terrible people. I guess the moral of the story is don’t be someone you’re not? Just be yourselves! “The Janitor Always Mops Twice” is a black and white film noir spoof that centers on Charlie as he seeks to uncover the culprit behind Frank’s unfortunate diarrhea poisoning. I love when Sunny gets thematic and/or pays homage to cinematic properties. As per usual, they knock it out of the park with all the glitz and glamour of old Hollywood. 

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Do you have any favorite episodes of It’s Always Sunny in Philadelphia? Sound off in the comments below!

 

 

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