It’s Always Sunny in Philadelphia is one of the most notable comedies of the 21st Century. Premiering in 2005, Always Sunny is now on its 15th season, making it the longest-running, live-action comedy series of all time, surpassing The Adventures Of Ozzie and Harriet. This kind of longevity did not come without challenges, as it was often a show that lived under the radar, finding a passionate fan base which kept it afloat.
Over the years, that fan base has continued to grow in large part because of the show’s many excellent creators, writers and performers, including Rob McElhenney, Glenn Howerton, Charlie Day, Kaitlin Olson, and Danny DeVito. As a resident of Philadelphia myself, I can think of nothing better than this show to represent my great city. Sure, this gang of misfits often make questionable decisions to say the least, but its creators know that the butt of the joke is always the characters themselves. Whether you are just getting into the show or are a longtime fan, enjoy this list of the 10 best episodes of It’s Always Sunny in Philadelphia ranked, from funny to downright hysterical.
10. ‘Chardee MacDennis: Game Of Game’ (season seven, episode seven)
Ah, yes! Chardee MacDennis, that classic board game that ranks alongside the likes of Monopoly, Clue, and Trivial Pursuit except, you know, with more drinking…a lot more drinking.
We’ve all been mind-numbingly bored on a rainy Saturday afternoon, but few of us have a board game of our own design to turn to during those times. The gang, it turns out, created Chardee MacDennis, a drinking game that fills the time while helping the players get obliterated beyond imagination. To quickly summarize a game that becomes increasingly complicated, it contains three main sections, mind (trivia, puzzles, artistry), body (physical challenges), and spirit (emotional battery and public humiliation).
By their account, the gang has played the game 17 times, and each time, Dennis and Dee beat Charlie and Mac. Ultimately, this time is no different, though how we get there is full of twists and turns. “Chardee MacDennis: Game of Games” also allows us to learn some trivia about the gang we might not even have known ourselves. For instance, “Dennis is asshole. Why Charlie hate?” Because, of course, “Dennis is a bastard-man!”
9. ‘Old Lady House: A Situation Comedy’ (season twelve, episode three)
“Old Lady House: A Situation Comedy” once again finds a way to play with the form of the show to hilarious ends. By this time in season 12, Charlie and Mac’s mothers have moved in together, despite not really getting along. Concerned about the situation, Charlie has decided to place cameras throughout the house. Dennis, who watches the videos from Paddy’s back office, sees this as an opportunity to spice things up for the ladies, turning their everyday actions into a sitcom-style comedy, replete with laugh tracks and a theme song. It’s a ridiculous setup played to absurd ends, but somehow it all works fantastically.
8. ‘The Gang Saves the Day’ (season nine, episode six)
When you are nine seasons into a show, you are allowed a certain amount of experimentation. “The Gang Saves the Day” presents just that opportunity.
The episode begins when the gang heads into a convenience store only to find them in the middle of an armed robbery. We then dive into a world of imagination, as each member pictures what they would do to save the day. Like “The Gang Gets Analyzed,” this episode gives insight into the characters and their individual neuroses. Mac, for instance, believes the situation will likely devolve into a full-on ninja fight where he will show off his impressive moves before tragically getting killed and ascending to Heaven. Meanwhile, Dee’s imagination ends with her somehow marrying both Josh Groban and Brad Pitt. The best, however, comes with Charlie’s vision. For some reason, it is in cartoon form and plays an awful lot like the opening moments of Pixar’s Up, but with significantly more rats involved. “The Gang Saves the Day” is another in a series of examples of how Always Sunny continues to take creative risks.
7. ‘The Gang Tries Desperately to Win an Award’ (season nine, episode three)
It’s Always Sunny has now run for a whopping 15 seasons, but they’ve yet to win a single Primetime Emmy. It’s a travesty, an embarrassment, and a sick, twisted joke. Then again, it did lead to one of the best episodes of the show, so it’s not all bad.
“The Gang Tries Desperately to Win an Award” is the most meta episode of the show the band has ever made, confronting head on the critics who do not deem them award worthy. Within the context of the episode, this takes the form of the bar not ever being awarded, which leads the gang to change the way they do things in an attempt to give the critics what they want. What do they think the critics want? Characters blasted with light and make-up, will-they-or-won’t-they plotlines, and a family-friendly theme song. Of course, this being the gang, it all blows up in their faces and ends in violence, disturbing sexuality, and a whole lot of spitting. Maybe there is a reason they’ve never won an award.
6. ‘Mac & Dennis Move to the Suburbs’ (season 11, episode five)
As a man who grew up in the suburbs of Philadelphia, this one hits particularly close to home. “Mac & Dennis Move to the Suburbs” focuses almost exclusively on, you guessed it, Mac and Dennis, placing them in familiar roles as an old married couple.
This one takes “old married couple” idea more literal than ever, as the two leave the city and start a life in a quiet (too quiet?) suburb. Things immediately take a turn for the worse as Dennis finds the suburbs and the commute even more aggravating than the city. Meanwhile, Mac falls into the lonely, bored housewife role. The best moments of “Mac & Dennis Move to the Suburbs,” though, come from Glenn Howerton’s performance as Dennis. Rage and slow-boiling insanity have been his bread and butter throughout the series, but this one takes it to a new level as his road rage and neighborly hostility reach a tipping point.
5. ‘Reynolds Vs. Reynolds: The Cereal Defense’ (season eight, episode 10)
Lots of court cases have been deemed “The Trial of the Century,” but they all pale in comparison to “Reynolds vs. Reynolds: The Cereal Defense.” It’s a case that has it all: slander, donkey brains, red wine, evolutionary debates, and sloshing bowls of cereal. Like “Chardee MacDennis,” this is an episode that takes place largely within the confines of the bar and again shows the lengths the gang will go to win, whatever the competition.
The episode works mostly because of both the absurdity of the situation and the kind of warped logic of the debate. It all starts when Frank rams into the back of Dennis’ car while he is parked, sending the bowl of cereal he was eating all over the interior of his Range Rover (aka his finisher car). Why was he eating a bowl of cereal in the car? Excellent question. Why did Frank run into him? Well, that’s complicated. Could a race of X-Men-like creatures evolve in real life? Maybe? These are the riveting questions “Reynolds vs. Reynolds: The Cereal Defense” attempts to answer.
4. ‘The D.E.N.N.I.S. System’ (season five, episode 10)
You could make an argument that “The D.E.N.N.I.S. System” might be the Sunny episode with the largest cultural footprint. The titular D.E.N.N.I.S. System, with all its horrific details, is definitely something people are aware of even if they only have a peripheral knowledge of the show. It’s around this time, at the tail end of season five, where we get the full picture of how sick and twisted Dennis Reynolds really is. I mean, we knew he was manipulative, vain, arrogant and possibly filming his sexual escapades without consent, but this episode lays everything out plain.
That’s not to say the rest of the gang show the best parts of themselves here either; we learn that both Mac and Frank have their own systems for picking up women, Charlie continues to stalk and harass The Waitress, and Dee treats Ben the Soldier to her own form of misguided manipulation. Of course, it all leads to Dee getting stabbed by a carny because, well, how else would it have ended?
3. ‘The Gang Gets Analyzed’ (season eight, episode five)
You are going to want to strap in for this one. “The Gang Gets Analyzed” is not the first time the show has delved into its characters’ minds, but it is certainly the most comprehensive exploration of their fractured psyches. What starts out as another in a series of sessions with Dee and her therapist turns into a full-fledged examination of each member of the gang, starting with Mac’s body dysmorphia and culminating in Dennis’ particularly unnerving brand of psychosis. This is something the show does masterfully as the seasons have worn on. Rather than continue to keep things more surface-level, they have fun getting to the root of what makes them tick and just why their dysfunction runs so deep. The gang themselves are not too open to such self-assessment; they just want to know who has to do the dishes.
2. ‘Who Pooped the Bed?’ (season four, episode seven)
It’s not a question anyone should have to answer, yet here we are. This season four episode sees the majority of the gang working diligently to uncover the age-old question, who pooped the bed?
The issue at hand stems from the living situation of the maybe-father-and-son duo known as the Gruesome Twosome, Frank and Charlie. Though it’s been displayed time and again that Frank Reynolds is a wealthy man with cash to burn, he has, at this point in the series, decided to live full-time with Charlie, sharing a single pullout couch. It’s in that very couch-bed that the two find the poop in question, perfectly placed between the two of them in a way that keeps the pooper a mystery.
Dennis and Mac are quite intrigued and agree to help get to the bottom of this truly existential question. Meanwhile Dee, disgusted by the poop shenanigans, attempts to recreate her friendless life into an episode of Sex And The City by inviting The Waitress and Artemis out for a night on the town. It’s the way this episode winds itself around and is able to wrangle the threads into one incredible ending that make it such a treat. Then of course, there’s the simple fact that, as we all know, poop’s funny.
1. ‘Mac and Charlie Die Pt. 1 and 2’ (season four, episode five and six)
This one holds a special place in my heart as the first episode of Always Sunny I ever saw. It’s a day I can remember quite well, sitting on a friend’s couch. His older brother sang the praises of this weird show on something called FX, where characters yell over each other in what appears to be genuine, vitriolic anger. I was hooked immediately. Something about the combination of humor, the way the stories seemed less forced than your typical sitcom, and the naturalist way these characters interacted felt exciting and different. It’s also a series of episodes that feature, among other things, paternal death threats, a glory hole, an abandoned wedding dress, and European anonymous sex parties. Honestly, what’s not to like? I might not have known this would become my favorite show of all time, but I certainly knew I’d be watching a few more episodes after getting a taste of Always Sunny.