It’s Always Sunny in Philadelphia is a sitcom unlike any other. The series follows the lives of “The Gang”, a group of five detestable, inconsiderate, vindictive individuals who together own Paddy’s Pub and wreak havoc across Philadelphia any chance they get.
Fans of the show have loved to hate the Gang for the last two decades, and for good reason. It’s Always Sunny masterfully blends satire and social commentary with outrageously ridiculous situations, from childish feuds with fan-favorite secondary characters and insane ideas like Fight Milk and Wolf Cola, to therapy sessions gone wrong and basically anything else you can imagine.
If you can think of a dumb idea, chances are Dennis Reynolds (Glenn Howerton), Sweet Dee Reynolds (Kaitlin Olson), Charlie Kelly (Charlie Day), Mac (Rob McElhenney) or Frank Reynolds (Danny DeVito) has tried it.
Whether you’re looking to get into the series for the first time or you want to rewatch it for the 10th, you’re in luck. This post goes through the 30 funniest episodes of It’s Always Sunny in Philadelphia for your viewing pleasure.
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From highest-rated episodes to hidden gems and everything in between, you can’t go wrong with any of these 22-minute episodes of comedy gold.
The Nightman Cometh (Season 4, Episode 13, 2008)
The musical episode that brought us the “troll toll” and one of Charlie’s most iconic alter-egos, Day Man. In it, Charlie stages an elaborate musical production to win the Waitress’s heart, but his unsettling and bizarre content leaves the gang—and the audience—baffled. The satire highlights Charlie’s misguided romantic gestures and the gang’s unrelenting self-absorption. This cult-favorite episode turns absurdity into an art form.
CharDee MacDennis: The Game of Games (Season 7, Episode 7, 2011)
The Gang showcases their homemade, sadistic board game, where cheating and emotional warfare are not just allowed, but encouraged (for Dee and Dennis, anyway). The absurd rules and juvenile rivalries quickly devolve into chaos and escalating violence. Satirical absurdity reigns supreme in this fan-favorite entry.
The Waitress Is Getting Married (Season 5, Episode 5, 2009)
Charlie spirals when the Waitress announces she is engaged, leading him down a deeply deranged path of trying to ruin the Waitress’s life. Dee, on the other hand, disastrously attempts online dating, exposing her own flaws in the process. The gang’s behavior reaches new lows as they turn romantic rejection into absurd melodrama.
The Gang Misses the Boat (Season 10, Episode 6, 2015)
When the Gang briefly decides to go their separate ways, each member realizes how utterly dysfunctional and dependent they are on each other. From Dennis’ imploding narcissism to Mac’s troubling new friendships, the episode is a darkly humorous critique of co-dependency and personal stagnation.
The Gang Gets Invincible (Season 3, Episode 2, 2007)
Inspired to go out for the local tryout for the Philadelphia Eagles, the Gang delves into delusional fantasies of athletic glory. Even if their total lack of talent didn’t ruin their chances at fame, Frank and Charlie tripping in the parking lot (with Charlie wearing the green man costume) certainly did.
The Gang Gets Analyzed (Season 8, Episode 5, 2012)
When Dee forces the Gang to attend therapy, their deep-seated issues and toxic dynamics are hilariously exposed. Each member’s inability to self-reflect becomes a scathing satire of modern self-help culture and therapy stereotypes. It’s dysfunction at its finest.
Sweet Dee Has a Heart Attack (Season 4, Episode 10, 2008)
Health scares lead Dee and Dennis to attempt to pursue healthier lifestyles, while Charlie and Mac attempt to make it big in the corporate world. Both parties’ attempts immediately – and hilariously – go array, satirizing society’s obsession with quick fixes and absurd workplace dynamics.
The Gang Broke Dee (Season 9, Episode 1, 2013)
After years of mistreatment, Dee reaches a breaking point, leading her to a breakdown and the Gang to exploit her apparent vulnerability for their gain. The episode is a biting commentary on group dynamics, manipulation and the lengths people go for personal validation.
Flowers for Charlie (Season 9, Episode 8, 2013)
Charlie becomes the subject of an experiment to increase his intelligence, leading to absurd results and an inflated ego. Meanwhile, the Gang gets caught up in bizarre side plots. A clever adaptation of “Flowers for Algernon”, the episode hilariously critiques arrogance, pseudo-science and the pursuit of intelligence without wisdom.
Hero or Hate Crime? (Season 12, Episode 6, 2017)
When the gang finds a winning scratch-off ticket, they all feel entitled to it. What ensues next is a hilarious debate over morality, identity and virtue signaling. As each member of the gang makes a claim for the ticket, the episode bounces from the lawyer’s office to the scene of a crime, showing just how ridiculous the whole situation is to anyone other than the Gang.
The Gang Buys a Boat (Season 6, Episode 3, 2010)
For those familiar with It’s Always Sunny, you know about “The Implication.” The Gang’s dream of buying a boat quickly devolves into chaos. Dennis’ unsettling monologues and the Gang’s dysfunction turn this simple purchase into a darkly comedic disaster.
The Gang Tries Desperately to Win an Award (Season 9, Episode 3, 2013)
Frustrated by their lack of recognition, the Gang attempts to make Paddy’s Pub more “award-worthy,” only to double down on their bad behavior. Their misguided efforts explore the pursuit of external validation and the inauthenticity of awards culture. It’s a satirical masterpiece of pettiness.
The D.E.N.N.I.S. System (Season 5, Episode 10, 2009)
Dennis unveils his manipulative and sociopathic system for seducing women, horrifying even the Gang, if you can believe. The episode explores the normality of toxic masculinity and emotional manipulation, despite how clearly wrong it is when it’s laid out on a posterboard. It’s both darkly funny and deeply unsettling.
Charlie Work (Season 10, Episode 4, 2015)
Charlie single-handedly saves the bar from a health inspection in a brilliantly chaotic, single-take sequence. His underappreciated ingenuity highlights the Gang’s incompetence while parodying the thankless nature of labor. It’s a rare glimpse of Charlie’s surprising capabilities amidst his usual nonsense.
Mac & Dennis Move to the Suburbs (Season 11, Episode 5, 2016)
Mac and Dennis’ attempt to live in the suburbs spirals into madness as they confront boredom and each other’s unattractive habits. The episode hilariously exaggerates the clash between urban chaos and suburban monotony. It’s a satirical take on the illusion of a simpler life.
The Gang Goes to a Water Park (Season 12, Episode 2, 2017)
The Gang’s trip to a water park turns into a series of outrageous schemes, from faking terminal illnesses to cut the lines to Dennis taking a young boy “under his wing.” Their antics lampoon entitlement, rule-breaking and the chaos of public spaces. The episode is both hilarious and uncomfortably relatable.
Mac Finds His Pride (Season 13, Episode 10, 2018)
Mac comes to terms with his identity through a heartfelt and unexpectedly moving dance performance. The episode blends absurd humor with a rare moment of emotional depth, making it a one-of-a-kind episode for this darkly comical series.
Dennis and Dee Go on Welfare (Season 2, Episode 3, 2006)
After considering hard work and determination, Dennis and Dee instead fake their way into the welfare system, spiraling them into absurd laziness and crack addiction, of course. Their descent into squalor explores stereotypes about government aid while exposing their own privilege and incompetence. It’s satire wrapped in chaos.
The World Series Defense (Season 5, Episode 6, 2009)
The Gang recounts their misadventures during the 2008 World Series, spinning wildly self-serving tales to justify their rowdy behavior and legal troubles. From Mac’s overblown patriotism to Dee’s misguided schemes, their antics escalate in hilarity and absurdity. The episode humorously highlights their unshakable entitlement and knack for turning celebration into chaos.
Wolf Cola: A Public Relations Nightmare (Season 12, Episode 4, 2017)
The Gang faces backlash when Frank’s beverage company, Wolf Cola, becomes embroiled in scandal, highlighting their total lack of ethics or accountability. The episode is a scathing satire of corporate PR and damage control. It’s absurd, dark and hilariously tone-deaf.
The Gang Goes to the Jersey Shore (Season 7, Episode 2, 2011)
The Gang’s beach trip goes exactly as you’d expect it to, from Frank’s questionable adventures to Dee and Dennis’ nostalgia gone awry. Playing on vacation expectations versus reality in the most outrageous way possible, this beach day is equal parts wild and cringe-inducing.
Dennis Takes a Mental Health Day (Season 16, Episode 3, 2023)
Dennis’ attempt to relax and take a break from the Gang leads to a breakdown of his own fragile psyche. The episode lampoons self-care culture and the absurdity of Dennis’ meticulously crafted persona. It’s a darkly funny exploration of his narcissism, showing audiences just how despicable he is as a character.
The Gang Hits the Road (Season 5, Episode 2, 2009)
A road trip to the Grand Canyon in a compact car with a U-Haul turns into a series of disastrous and wildly inefficient detours. The Gang’s inability to work together and Charlie’s fear of leaving Philly highlights their dysfunction in a satirical take on the classic road trip.
The Gang Goes on Family Fight (Season 10, Episode 8, 2015)
The Gang’s appearance on a game show showcases their toxic dynamic, lack of knowledge and utter disregard for rules. The episode is a hilarious play on reality TV and the competitive family game trope. At least they didn’t try to play CharDee MacDennis.
Mac Bangs Dennis’ Mom (Season 2, Episode 4, 2006)
In this chaotic episode, Mac decides to pursue Dennis’ manipulative and narcissistic mother as a twisted form of revenge. Meanwhile, Charlie schemes to win the affection of the Waitress through a convoluted and deeply misguided plan. This episode masterfully explores the absurd lengths people will go to out of spite or infatuation.
Frank vs. Russia (Season 13, Episode 4, 2018)
Frank takes on an underworld figure in a bizarre wrestling match that highlights his mysterious past and his obscene hubris. A fan-favorite – as most Frank-focused episodes are – the episode plays on fear of aging, bravado and the absurdity of Frank’s shady exploits.
Making Dennis Reynolds a Murderer (Season 12, Episode 5, 2017)
When Dennis is accused of murder, the Gang creates a wildly biased documentary to clear his name. The episode hilariously echoes true-crime documentaries while delving into Dennis’ sociopathic tendencies.
The Gang Hits the Slopes (Season 11, Episode 3, 2016)
A ski trip becomes a satirical homage to 80s teen movies, complete with rivalries, outrageous outfits and over-the-top montages. The Gang’s antics brilliantly subvert nostalgic tropes.
Dee Day (Season 14, Episode 3, 2019)
Dee enforces her own day of self-indulgence, forcing the Gang to follow her bizarre rules. The episode dives into gender roles, power dynamics and the Gang’s endless pettiness.
The Gang Tends Bar (Season 12, Episode 8, 2017)
The Gang attempts to host a functional night at Paddy’s Pub after Dennis convinces them it’s time to turn a new leaf. But with the packed bar and a mysterious crate left in the alley, what else can the gang do other than completely upend their chance at some semblance of success?
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There you have it: the 30 funniest episodes of It’s Always Sunny in Philadelphia. And with the all-new season 17 set to air sometime in 2025, now’s the perfect time to get on board with the Gang’s antics.
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Frequently Asked Questions
How many seasons of 'It's Always Sunny in Philadelphia' are there?
16
Who are the main characters in 'It's Always Sunny in Philadelphia'?
The main characters are Dennis Reynolds (Glenn Howerton), Sweet Dee Reynolds (Kaitlin Olson), Charlie Kelly (Charlie Day), Mac (Rob McElhenney) and Frank Reynolds (Danny DeVito).
What are some of the funniest episodes of 'It's Always Sunny'?
Funniest episodes of 'It's Always Sunny in Philadelphia' include Sweet Dee Has a Heart Attack (Season 4, Episode 10, 2008), Charlie Work (Season 10, Episode 4, 2015), The Gang Goes to a Water Park (Season 12, Episode 2, 2017), The Gang Goes on Family Fight (Season 10, Episode 8, 2015), The Gang Tends Bar (Season 12, Episode 8, 2017), and so many others.
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