Funniest Charlie Moments In It’s Always Sunny In Philadelphia

The eighth season of It’s Always Sunny In Philadelphia features an episode in which the entire gang of bar-owning miscreants agrees to get psychoanalyzed by Dee’s therapist. Throughout the episode, the therapist, portrayed excellently by Reno 911′s Kerri Kenney, suffers through the most absurd one-on-one therapy sessions ever depicted on television.

In a scene that would make Tony Soprano look like a psychiatrist’s dream client, Charlie explodes into a fit of rage, explaining his erratic behavior, such as foraging for discarded denim and old coins in the sewers, as well as his mysterious origins as a survivor of an abortion attempt, before pulling a dead pigeon out of his shirt pocket and throwing it into the air, only to land bluntly on the therapist’s coffee table. Charlie resolves at the conclusion of his session that, like all bizarre choices he’s made in his life, he’ll adjust to it and make a tradition out of it.

After spending five seasons pining after the aloof coffee shop waitress, Charlie becomes despondent upon learning that she has become engaged to Brad Fisher, a former classmate from high school who spent his teen years mired with horrific acne. After growing into his beauty in adulthood, Brad conspires to date the women who wouldn’t pay attention to him in school, only to dump them in a highly disrespectful manner or even leave them at the alter during their planned wedding.

Before taking revenge on Brad by delivering him a giant box filled with furious hornets, Charlie engages in one of the funniest interactions in Always Sunny In Philadelphia history. In one scene, Mac and Dennis attempt to build Charlie’s dating profile, leading to an exchange that has Charlie referring to his favorite dinner, milk-steak, boiled over hard, paired with jelly beans (raw, of course), as well as listing his favorite things, which include magnets and little green ghouls.

Season 9 of It’s Always Sunny In Philadelphia features an episode so far ahead of its time that it was revisited ad nauseam during the 2020 COVID-19 pandemic. In “The Gang Gets Quarantined,” Danny DeVito‘s Frank Reynolds becomes concerned about the sudden uptick of flu cases plaguing Philly, forcing the gang to hole up in Paddy’s Pub as they each slowly find new and creative ways to get themselves sick.

Charlie is, at first, the only character who comes prepared. Taking a page from the book of his OCD-stricken germaphobe mother, Charlie snags a pair of hazmat suits to brave the elements of the local gas station for snacks and drinks. After nearly everyone in the gang winds up locked in the bathroom, suffering from what turns out to be alcohol withdrawal, Charlie storms into the quarantine zone out of nothing but pure boredom, with a set of keys in his pocket the entire time.

In an It’s Always Sunny In Philadelphia episode, which has become rife with memes and GIFs on social media, Charlie, Mac, and Dennis attempt to solve the nationwide gas crisis by siphoning gasoline and selling it door to door. After a series of roadblocks get in the way of their ingenious business model, the three struggle to properly categorize their roles within the group.

After settling on the role of “Wild Card,” Charlie determines it is his sole mission to sew chaos and discord within the group, culminating in an epic moment in which he cuts the breaks of the gang’s van, sending everyone blasting down the road to certain destruction. After revealing to the gang that he cut the brakes, Charlie shouts, “Wild card, bitches! Yeehaw!” and leaps from the back of the moving vehicle, in a move that would later become an iconic running gag in the series.

In the tenth season of Always Sunny In Philadelphia, Keagan-Michael Key guest stars as the host of the beloved game show, Family Fight, becoming increasingly exhausted with the antics of the gang as they compete against an average American family. The fictional show serves as a clear stand-in for Family Feud, in which contestants answer questions to determine how many surveyed strangers would respond to a prompt.

As the episode progresses, Charlie continues answering the prompts in the most absurd way possible, winning a singular point on each guess. This gives way to Charlie suggesting that human beings of a certain status regularly consume dragon meat, while dragons prefer the taste of gold coins and treasure over human flesh. Eventually, Charlie remembers that he himself took this survey during a recent mall outing, guaranteeing the gang a single point every time he answers.

Charlie’s entrepreneurial spirit is seen throughout the series, with he and his cohorts frequently crafting some of the wildest inventions known to mankind throughout the run of It’s Always Sunny In Philadelphia, including a shotgun that blasts alcohol into your mouth, a milk and crow egg-based energy drink for bodyguards, and a stress ball, which is really just an egg painted green. In a season 5 episode, Charlie creates the now-famous Kitten Mittens and even shoots his own poorly edited promo video to advertise them to potential investors.

The video features hilarious quotes from Charlie, such as “Is your cat TOO LOUD?!” and “Kitten Mittens, you’ll be smitten!” Leaving the rest of the gang to wonder what prompted this sudden engineering spirit. Charlie then goes on a tirade about the dozens of cats making noise in his alley and his own cat food-eating habit, which inspires the cat’s unshakable devotion.

One of the most iconic episodes of It’s Always Sunny In Philadelphia follows the gang as they struggle to put on a stage show written by Charlie, titled “The Nightman Cometh.” The show includes a number of musical numbers, with each member of the gang getting their own solo number in addition to a few ensemble songs strewn throughout the production.

Early in the episode, the gang grills Charlie on why he decided to write a play, with Dennis and Mac asking what he stands to gain from the endeavor. In the show’s final moments, Charlie emerges from the rafters on a descending set, singing a barely scripted song about his journey through manhood and begging the coffee shop waitress to marry him. As usual, the waitress only showed up to the play in an effort to get Charlie to leave her alone, causing her to reject his advances yet again and storm out of the audience.

The Pepe Silvia monologue that Charlie delivers in Always Sunny In Philadelphia‘s Season 4 episode “Sweet Dee Has A Heart Attack” has gone down as one of the greatest and most memed scenes in comedy television. In the scene, Charlie describes his growing madness at the existential nightmare of life in a modern office, with his own illiteracy making his job sorting mail for the corporation essentially impossible.

Standing before a wall of conspiracy threads linking photos and bizarre scrawlings to one another like an insomnia-riddled detective searching for the Zodiac Killer, Charlie launches into a tirade about the lack of evidence to support the existence of Pepe Silvia, a man who Charlie claims has been receiving hundreds of unclaimed parcels.

While some fans have suggested that Pepe Silvia is really a stand-in for Charlie’s misreading of Pennsylvania, the writers have debunked this claim, with Mac even stating in the scene, “Okay Charlie, I’m gonna have to stop you right there. Not only do all of these people exist, but they have been asking for their mail on a daily basis!”