It’s Always Sunny in Philadelphia has persisted for well over a decade thanks to both its raunchy yet witty writing and its talented cast. While every cast member has contributed plenty to an already energetic formula, many fans have heralded Charlie Kelly as the standout member.
Despite being the grunt of Paddy’s Pub, Charlie often steals the show with his manic energy, inherent sympathy, and a backstory that only becomes more and more tragic as the story goes on. Unsurprisingly, that incredible energy and smart delivery has developed some of the best episodes in the series’ long history.
10 McPoyle vs. Ponderosa: The Trial Of The Century (8.6)
Charlie Kelly is the law’s best-kept secret, mostly because he’s far from the most ideal representation for a court case. Unfortunately for Bill Ponderosa, there weren’t many options available when the McPoyles wanted recompense for their disastrous wedding in the episode “The Maureen Ponderosa Wedding Massacre.”
Here, Charlie pulls out all the stops of his very limited vocabulary in law (and, in all honesty, English) to make a case for Bill, including everything from dragging out surprise witnesses to exhibiting his expertise in “Bird Law.”
9 The Janitor Always Mops Twice (8.6)
It’s Always Sunny doesn’t always do parodies; but when they do, it’s always a showstopper. In their wonderful spoof of neo-noir flicks, Charlie has to clean up the aftermath of Frank getting food poisoning, both in terms of finding out who poisoned him as well as literally cleaning up the mess as a janitor.
It’s a good thing that this episode is in black-and-white. His investigation puts him at odds with the rest of The Gang, as he dives into a sticky mystery involving the waitress and a cherry conspiracy. When he gets too close to the case, things start to run red.
8 The Waitress Is Getting Married (8.8)
Charlie’s troubled history with The Waitress is a well-documented one, particularly in The Waitress’ restraining orders. In this episode, The Gang does their best to keep Charlie from discovering her upcoming engagement, knowing full well how that would destroy him as well as how they would be left to clean up the bar.
This leads Mac and Dennis to arrange a blind date for Charlie via preparing an online, dating profile that is the furthest thing from descriptive of Charlie. However, no amount of tricks or makeup can hide what Charlie truly is inside, and Charlie takes the date off what few wheels it was already on.
7 Flowers For Charlie (8.8)
One of the biggest problems for Charlie as well as The Gang as a whole is his illiteracy. Due to an unstable childhood and years of drug abuse, Charlie has become the bumbling moron that The Gang is always ready to abuse. That same ignorance, however, is what made him a prime candidate to test out a new drug meant to increase one’s mental capacity.
As the experiment went on, Charlie became more and more arrogant. He started using a more complex vocabulary, began playing a long series of Chess games, challenged The Gang and Frank with his newfound intelligence, and even broke things off with The Waitress. This episode truly does dare to ask what the true price of intelligence is.
6 Sweet Dee Has A Heart Attack (8.9)
Given that The Gang runs a very sloppy bar, one has to wonder how these people could possibly afford health insurance. As it turns out, they can’t. After Dee gets a sudden heart attack, the entire group starts to become health crazy. While she and Dennis resort to a variety of fast track health methods, Charlie and Mac decide to get health benefits as mail clerks at a local office.
Here, they start their various misadventures as office dwellers, using only prior knowledge from ’80s movies to guide them. As Mac tries to mingle with the upper management, Charlie’s extended time in the mailroom brings him down a dark, conspiratorial path to enlightenment.
5 Dee Reynolds: Shaping America’s Youth (8.9)
The Gang has a very fragile chemistry that is quickly offset if the group either separates from one another or Paddy’s Pub. This is most evident in “Dee Reynolds: Shaping America’s Youth,” in which, Dee and Charlie decide to leave Paddy’s Pub to get new jobs at their old high school.
While Dee shapes young minds as a drama teacher, Charlie tries to mentor the kids from his influential spot as a janitor. While the position isn’t a huge upgrade from his spot at Paddy’s, it did give a prime opportunity to talk and advise the next generation, a prospect that proves that not everyone is cut out to be a teacher and that schools really should take hiring their custodians seriously.
4 Charlie And Dee Find Love (8.9)
After Charlie takes one of his harshest rejections from The Waitress yet, he and Dee come across two very good looking and very rich siblings from one of Philly’s most powerful families. They begin seeing the siblings, leading Dee to have a very one-sided romance with the brother and Charlie to have a surprisingly intimate relationship with the sister, played by Alexandra Daddario.
Things really heat up when Charlie seemingly confronts The Waitress one last time to see if he was still in love with her only to see the aftermath of Frank’s recent sabotaging of her. Will Charlie stick with the girl who clearly loves him back or will he return to The Waitress during a time when she truly needs him?
3 Mac & Charlie Die: Part 1 (9.0)
When Mac’s father, Luther, is announced to be on parole soon, the duo tries to testify against him to keep him in jail. This is mostly because of their tumultuous history with him and the fact that they’re really scared of what Luther might do to them.
After that fails in grand fashion, the two resort to the only other alternative: faking their own deaths. In their convoluted attempts to stage their deaths, Mac gets a massive concussion and wears a wedding dress, Charlie shoots at Dee’s car, and the two prepare a very demanding, video will.
2 The Nightman Cometh (9.7)
It’s disappointing that Charlie is often synonymous with being the dope of the group, given that he’s easily the most creative and artistically talented out of all of them. There’s no better example of this than in “The Nightman Cometh,” in which he directs a play that is definitely not meant to win the heart of The Waitress.
In a Kubrickian display of arrogance and perfectionism, Charlie gets increasingly frustrated as The Gang proves to be really uncooperative, leading him to either yell at or manipulate the crew to get some semblance of what his vision was. What ensues is The Gang constantly trying to make the show about themselves and a very revealing display of Charlie’s complicated history.
1 Charlie Work (9.8)
It’s easy to see Charlie as the sidekick of the group. He rarely dictates The Gang’s various grifts and schemes and is often made to do the bulk of the work. Despite his low, hierarchical status, Charlie is, in fact, one of the most important members of Paddy’s Pub. In “Charlie Work,” the fans get to see how hard Charlie works to actually keep the seedy bar running.
Here, Charlie showcases how focused he can really be and how he can assume a leadership role when the going gets tough, and it does get tough when the bar’s scheduled inspection happens to be on the same day that the rest of The Gang tries to stage an airline scam. To make things even better, the second half of this episode show how talented Charlie and the rest of the cast really are as they pull of an impressive, continuous shot.
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