20 Of The Most LOL Moments From 'Always Sunny'

The twelfth season of It's Always Sunny In Philadelphia is currently on air, and over the years, The Gang - bartenders Dennis Reynolds, his sister Dee, their father Frank and their friends Mac and Charlie - has made us laugh until we cry by getting into all types of trouble. It was hard to narrow down the best moments out of over 120 episodes, but the 20 instances below are the ones that made us LOL the most.

From musicals and new jobs and relationships to hijinks involving pageantry, laugh tracks and dream books, we hope the humorous summaries below provide laughs. Share the most laugh-worthy Always Sunny episodes in the comments!

20 When Charlie Has Cancer

The episode with this same name is an iconic initial introduction to IASIP. Those who have seen behind-the-scenes moments of this show know that Kaitlin Olson’s audition included lines from the opening scene, during which Charlie and Dennis discuss the possibility of Charlie having cancer. Of course, as the summary of the series even points out, these characters are narcissists...so why would anyone truly show that they care about Charlie’s health scare?

Charlie finds out he might have cancer and just wants someone to talk to, but Dennis doesn't realize that he wants to talk right then; Mac and Sweet Dee are waiting for Dennis, who was just going to zip in and out...so he slips out of Charlie's apartment, putting cancer on the back burner.

19 When Dennis And Dee Go On Welfare

Via Playbuzz

In Season 2’s Dennis and Dee Go On Welfare, the two do get a genius idea to go on welfare, which means they quit their jobs, buy some chains and put on some gangster rap - because why not? The idea came about due to Frank’s bossiness, since he’s the new owner of Paddy’s Pub. This is one of the many times that the twins promise to go chase their dreams again; they shouldn't be bartending - and they can even make more income with help from the government. However, they end up addicted to crack and back at the bar, doing Charlie’s work, so that Frank can teach his kiddos a lesson. Despite a tragic ending, they will always have their one afternoon of freedom, during which they sat...drunk...on porch steps...in the middle of the afternoon...singing Just a Friend by Biz Markie.

18 When Sweet Dee Dates Lil Kev

Via Pinterest

We’ve been introduced to several of Dee’s love interests - The entire series even starts out by doing so! - but perhaps her most memorable boyfriend was Lil Kev, the intellectually disabled rapper from Season 3. Kevin Gallagher went to elementary school with Dennis, and years later, Dee ends up dating and dumping him; he actually isn't actually intellectually disabled despite what Dennis says, and even slams Dee in front of everyone at the bar through a colorful rap song. Even though he’s able to throw some shade her way, he does live with his mom, does not drive and does wear his T-shirt backwards, which Dee points out, as she questions what she’s doing with her life.

She breaks up with Lil Kev while the two are watching cartoons. He’s is laughing it up, throwing popcorn into his mouth and washing it all down with a juice box. He doesn’t even care about his shirt which seals the deal for Dee: “We need to break up.”

17 When Charlie Writes The Nightman

In the same episode, Charlie sees the light (literally) and creates one of the first musical hits of the show: The Nightman. The Gang gets all worked up about an upcoming concert taking place at the pub; a music store and a hotel room are both destroyed during the process, and weird costumes are showcased, since no one can agree on one band look. To prepare, Charlie locks himself in his dark apartment and huffs paint, coming up with a twisted song about a “nightman”. When Dennis comes in and pulls down the curtain on Charlie’s window, creativity hits, and they realize that the song also needs a “dayman”. The two start singing and dancing together, creating a song that goes from just focusing on being “left in a world of darkness” to celebrating karate and friendship for everyone!

16 When Charlie Goes Crazy At An Office Job

In Season 4, Dee is hospitalized for a heart attack, causing Charlie and Mac to work in an office so they can have health insurance. There, Charlie goes on a wild hunt involving the mail and the name Pepe Silvia that keeps popping up. When Charlie explores the office, though, there is no Pepe Silvia, so he goes to Carol in HR, but...There...is...no...Carol. Mac steps in to inform Charlie that not only do all of these people exist, but they're all searching for their mail that Charlie is neglecting to deliver.

15 When The Gang Gets Extreme: Home Makeover Edition

Every now and again, the characters try to be good people, like a few episodes later, when they are inspired by Ty Pennington. They pick out a family and decide to redo the family’s home; however, Dee’s Spanish is a little broken, and with Mac’s menacing motions, it seems the family is in for trouble...which, with these bartenders involved, of course they are. Dee ends up telling the family that they'll lose their house and their lives, all for the sake of extreme television. Then, their house is completely destroyed, and they are forced to get a credit card for the $3,000-worth of homewrecking supplies The Gang bought. Welcome to America! And Dee...Work on Spanish.

14 When The Nightman Cometh

This is arguably the best episode of the entire show. Charlie writes a play, which is actually performed in front of a real-life audience (in real life). Everyone sings songs involving coffee and love, all so Charlie can propose to The Waitress. A giant sun floats down onto the stage, holding Charlie, dressed as brightly as the sun, singing about fighting The Nightman and asking The Waitress for her hand in marriage. When the big finish concludes, though, The Waitress just wants to know if that's it and if she can leave. Charlie demands an answer, and she tries to shut him down...but he reminds her that he will, of course, see her again tomorrow, since he must follow every move of the love of his life (who is also his real-life real love, since actors Charlie Day and Mary Elizabeth Ellis are married!).

13 When Charlie Salts Gail The Snail

Via Imgur

In Season 5, The Gang tries to do some good again, and this time, they target Frank. Frank is always using his connections and money to wrangle the group into more horrible ideas, and an afternoon at the park turned out to be a funeral...one in which Frank was just using to hit on his sister-in-law. That’s when it is realized that Frank might need professional help. After attempted therapy and having Gail the Snail (his niece) mash on Frank’s balls (since Mac tried to convince him to go after Gail, rather than Aunt Donna), everyone ends up back at the bar and considers the intervention a success; they tell the therapist to leave, sip wine out of cans and salt Gail the Snail away.

12 When We Learn About The D.E.N.N.I.S. System And What Men Do

Via Sceneclip

Dennis pretends to buy medications for his ill grandmother from Caylee, who works in a pharmacy and is his new love interest (also his wife in real life!), which Demonstrates value. He then invites her on a date, which leads to sex/Engaging physically. He pretends to be an angry/crazy person, calling Caylee and threatening her, which leads to her needing to lean on him even further - known as Nurturing Dependence. The threats get worse, though, all part of a plan in which he makes her feel horrible and Neglected emotionally...until he swoops in again and makes her feel like he is the love of her life (Inspire hope). But The D.E.N.N.I.S. System ends with Dennis Separating entirely and with Caylee leaving upset voicemails on his cell...which apparently just means that she really wants him - since that’s what men do!

He explains the entire dating process that he does, causing the men to hump the air and flex and do other “manly” things (since neglecting and separating are sooo manly), and Dee just stares at them, surprised that they believe such things work.

11 When We Learn Of Charlie's Dream Book

Via Flickr

Why is Charlie the one who has to do all the dirty work in the bar? Does he ever get thanked or paid for this? Do his so-called friends even realize what he goes through? This all gets addressed in Season 6, as a party is thrown for the King of the Rats. Regardless of the mishaps that occur while planning this surprise “birthday” party, Mac, Dennis and Dee are able to produce some special gifts for Charlie, all from his “dream book”. They try to decipher his weird drawings and illiterate writing and create denim chicken (a skinned rotisserie chicken in tiny denim pants), a bird with teeth (which they had to convince Charlie was not real, as the teeth were just glued into a skeleton) and “worm hat” (Is it a hat that makes one look like a worm? Is it a hat made out of worms? Or is it a teeny-tiny hat for a worm? All wrong...It’s Hans Worm Hat, a German guy who appears in Charlie’s dreams.).

10 When A Male Enters Frank's Beauty Pageant

Via Reddit

In Season 7, a beauty pageant is held, since new ventures and schemes are always being brewed up and attempted. Mac, Dennis and Charlie try to help the one young male who entered win, which results in a strange version of Yankee Doodle happening, during which “someone should have worn a shirt”. The little boy - the only boy in the pageant - loves to sing and dance and perform, but the shirtless techno version of this American classic went all wrong. The crowd looks uncomfortable, the boy rips off his red, white and blue sequined vest at the end, and the guys realize that maybe that was not the best approach to a win. It doesn’t matter, though, since Samantha won - She’s the prettiest, and that’s all that matters, right?

9 When Charlie And Dee Find Love

Charlie may not be the most handsome or the smartest of the group, but he has a shining moment in Season 8. While out stalking The Waitress, Charlie and Dee get rear-ended by a good-looking and well-off brother-and-sister duo, Trevor and Ruby. The four end up going on dates to restaurants (where Charlie even refrains from eating cheese...for a bit). This involves playing tennis, but in the end - of course - it all goes awry. Dennis finds out that Trevor is just using Charlie and Dee and assumes Ruby is, too. In a weird series of events, we also discover that The Waitress has been in an accident, and Charlie must go rush to his one true love, which upsets Ruby; Charlie claps back with facts that he knew Ruby liked him. He was using HER to make The Waitress jealous. He doesn’t consider Ruby a “woman of quality”, since she wanted sex early on in the relationship.

8 When The Gang Broke Dee

Season 9 brought so many greats, such as The Gang Broke Dee, during which an elaborate scheme is put in motion to help/break Sweet Dee. In one of the most elaborate Always Sunny tricks ever, the guys make Dee believe she’s finally getting famous from her comedy, going as far as to “fly” her to Conan (but she's really at Paddy’s, and everyone [except Dennis] has been in on breaking her down even more). The idea comes about when Dee is seen at an all-time low: eating month-old cake, smoking, not showering and finishing the guys’ insults before they can even get them out/not even being bothered by the fact that they think she’s a gross bird, since she’s so ugly she “can't even get a bus to hit on [her]”.

7 When The Gang Tries Desperately To Win An Award 

It’s Always Sunny In Philadelphia has been nominated for awards a few times but has only won a couple, including a 2016 People's Choice Award for Favorite Cable TV Comedy. We expect more after 12 years, though! Therefore, this Season 9 episode stands out due to the fact that the characters act like they’re fine with everyone liking classier, trendier bars better than Paddy’s Pub (much like the actors/actresses try to keep creating, despite the fact that other shows are receiving more awards). The Gang decides to try out one of these “cooler” bars, with its bartenders that act like they are on a primetime show, its regulars that know all the fun traditions (like drinking when a bell rings) and its cocktails full of fruit and color and exciting names.

As much as Mac, Dee and Dennis hate to admit it, they are kind of fond of the giant fishbowl drinks and find themselves caught up in the drama surrounding the bartenders of this “best bar”.

6 When The Gang Saves the Day And Charlie Floats Away

More hilarity ensues when we are given glances inside the characters’ heads. If they were all in a convenient store that was being robbed...

Mac would put his body guarding into motion and karate chop anyone standing in the way of safety. Dennis would only care about his shining - and fragile! - moments and female prize. Frank would only be concerned about many hot dogs he could eat in the midst of madness. Dee would finally get rid of the males holding her back and become a celebrity. Charlie would go full Pixar - marrying The Waitress, having lots of miniature waitresses/janitors and floating away in a house pulled by balloons.

While we loved all these alternate theories, we LOVED seeing Charlie get his happily ever Up after!

5 When There Are Flowers And Cheese For Charlie

This episode begins with The Gang arguing over who will be selected for an experiment - an experiment that rewards $1,000 and an experiment searching for a not-so-bright subject; the researchers find Charlie trying to grab cheese from a lab rat’s maze...but of course, Charlie isn’t going for the cheese that seems most accessible. He is determined to get the other piece of cheese, despite the fact that he is zapped every time he makes the wrong move. This unusual behavior makes Charlie the top pick for the experiment - an experiment that causes him to believe he’s suddenly a genius, listening to books on tape, speaking Mandarin (so he thinks) and not having any interest in his normal passions (even The Waitress!).

4 When Charlie's Work Is Never Enough

Via AV Club

In Season 10, all of Charlie’s janitorial work is put to the test on inspection day. A crate of chickens arrives, toilets are clogged, the carbon monoxide detector is turned off (as usual/thank goodness), and a truck driver shows up (for a separate scheme the other members of The Gang have going on), but Charlie goes into action mode, giving orders and making successful moves happen - without the inspector even noticing what’s going on!

In the end, he announces that they received the highest rating, but his buddies say they don't care; they always pass, without ever having to do "anything that special". Poor Charlie.

3 When Mac And Dennis Move To The Suburbs

Via Coub

Philadelphia is a great background to this show, but what happens when Mac and Dennis move to the suburbs? They start to go crazy - That’s what. Of course, a bet is going on, so they have to survive and cannot admit that they hate it. But the commute, the neighbors, the new/strange noises...The guys hate these things, but they begin to hate each other even more. Mac becomes the stay-at-home wife, cooking and cleaning and resenting Dennis for not helping, while Dennis stays aggravated all day, in rush-hour traffic and at work. These two lifestyles come to a head at dinner one night, when Dennis complains about yet another mac-and-cheese meal. Mac tries to explain how hard it is to be cooped up at home all day, but Dennis comes back with complaints about work - and the two continue to bicker like a married couple.

2 When The Gang Goes to Hell 

At the end of Season 11, The Gang Goes to Hell, in two parts and two episodes; Mac talks them all into taking a cruise...but it’s a Christian one that frowns upon their usual behavior, so they try to refrain from cursing, lying, drinking and so on. However, they end up thrown in cruise liner “jail”, trapped in a room that eventually begins flooding. The episode begins with The Gang dressed in white, in a bright-and-white room, talking about being sorry for their sins and how grateful they are to be saved. Part two ends with the light being lowered, though, since it was just a desk lamp at an office where a man tells them they are not legible for any compensation for the cruise ship’s emergency due to their crimes...Not heaven - or hell!

1 When The Old Lady House Turns Into A Situation Comedy 

Via Culturess

Twelve seasons later, Always Sunny is clearly still seeing success, with a huge cult following that appreciates the crass humor. Traditional comedy shows have certain positive traits, too, though, which The Gang tries out in A Situation Comedy; multi-camera views, a laugh track, music cues and predictable situations and characters are seen, as Dennis fills the back office of the pub with viewing monitors. “The grunty one physically abuses the shrill one, and the shrill one psychologically abuses the grunty one. And it really plays,” he says, speaking of Mac’s mom and Charlie’s mother. But then a possible ransom note shows up, which Charlie assumes means that Mrs. Mac is trying to kill his mom, and Mac’s mom then spills hot soup on Bonnie Kelly’s leg...causing her to aim a hammer over Mrs. Mac while she’s sleeping. Charlie writes the behavior off as comedy, though - They’re just like The Honeymooners!

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