It's Always Sunny In Philadelphia: 15 Worst Things The Gang Has Ever Done

It's Always Sunny in Philadelphia gang looking shocked

Since it premiered in August of 2005, It’s Always Sunny in Philadelphia has pushed the boundaries of what a television sitcom can get away with. Like Seinfeld before it, its main characters have gotten themselves into crazy situations and horrifying schemes due to selfishness and their endless pursuits of fame and fortune. Charlie, Mac, Dennis, Sweet Dee, and Frank represent the worst in all of us. They have no shame and will do pretty much anything to prove a point. But, then again, that’s what makes the show so hilarious. Every episode is a trainwreck of extremism you can’t help but watch as they make fools of themselves or put each other -- and everyone else who happens to wander into their path -- in danger.

While it was hard to narrow it down to just fifteen, this is a collection of some of the worst things the It’s Always Sunny gang has ever done over their twelve season (and counting) run.

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Kaitlin Olson and Rob McElhenney in blackface on Its Always Sunny in Philadelphia
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15 Wearing blackface in their productions of Lethal Weapon sequels

Kaitlin Olson and Rob McElhenney in blackface on Its Always Sunny in Philadelphia

Although they opened season 12 with an episode about becoming African-American versions of themselves (“The Gang Is Black”) by having different actors play the roles, in previous episodes, they just used blackface. Out of their passion for the Lethal Weapon movies, Dennis, Mac, Charlie, and Frank created their own sequel, Lethal Weapon 5, which was shown to a group of high school students, at Paddy’s no less. In true It’s Always Sunny fashion, they played all the characters themselves, including Danny Glover’s Roger Murtaugh character.

While there’s an in-depth conversation between Dennis, Frank, and Mac on the merits and controversy of using blackface and other inappropriate physical stereotypes, ultimately, Mac’s portrayal of Murtaugh inspires an impressionable student to show up to school in blackface, getting Charlie and Sweet Dee fired.

Then, as if using blackface once wasn’t enough, they make a sequel to their sequel during season 9. Lethal Weapon 6 has both Mac, reprising his role as Murtaugh, and Sweet Dee as his daughter, Rianne, in full blackface. While it’s obviously super offensive, somehow the cheesiness of the entire fan film charade still makes it funny in an awkward sort of way.

14 Encouraging underage drinking in their bar to turn a profit

Charlie Day tells off a teen in Paddys Bar

During an unusually packed night at Paddy’s, the gang realizes that most of their customers in the bar that evening are underage. After Dennis kicks everyone out, they all regroup to discuss how so many kids got into the bar in the first place. At first, most of the gang talks sense about not letting kids drink, but then Mac proceeds to convince them that teenagers need a safe place to indulge. He even goes so far as to say they’d be doing something good, as if letting underage kids drink is a form of community service.

Eventually, even Dennis chimes in, suggesting they water down the drinks to make a profit off the unsuspecting youth. As with everything else on this show, they find a way to rationalize what they’re about to do (and this is only the third episode). At least Dee tries to call them out, commenting, “I don’t know how you guys live with yourselves,” to which they reply appropriately, “one day at a time.”

13 Trying to mooch off unemployment and welfare

Kaitlin Olson as Dee and Glenn Howerton as Dennis in Its Always Sunny

Spoiled entitled people that they are, it’s no surprise that Dennis and Dee attempted to mooch off unemployment benefits and welfare at one point. In season two, they can’t stand working for Frank after he becomes the new owner for Paddy’s, so they quit to follow their supposed dreams. At first, Dennis sees their newfound freedom as an opportunity for achievement, but Dee has other plans for them.

After qualifying for unemployment, they spend their days getting drunk on their stoop, listening to Biz Markie, and being genuine a-holes. Unfortunately for them, unemployment runs out after a few weeks in Philadelphia, since they weren’t actively looking for work, so welfare becomes their next target.

Even though Mac points out that welfare’s for people who actually need it, Dennis and Dee hatch a scheme to pose as a recovering crackhead and his retarded sister. When their plan is foiled by a sassy government employee who demands actual proof of their states of mind, they decide to smoke a little rock in order to prove their crack addiction. Although actually getting addicted wasn’t in the cards, it just goes to show how far they’ll go to get their own way.

12 Exploiting a baby they found in a dumpster

Its Always Sunny gang with Dumpster Baby

Even the gang’s supposed good deeds turn sour when they think they can profit off them somehow. Such was the case with Dumpster Baby, or D.B. for short. Mac and Dee decide to take care of the little guy out of the goodness of their hearts, or at least until they get tired of him. But then, as they contemplate putting him back in the trash for someone else to find, a young woman tells them D.B. could be a Gerber baby.

Hoping to make D.B. into a star, they take him to a commercial agency, only to find out there’s a surplus of white baby actors. Latino babies, on the other hand, are in high demand. After asking the casting agent if there’s anything else they can do, she replies, “Not unless you can change the color of this baby’s skin.” Big mistake.

Mac and Dee take this advice seriously and bring D.B. to a tanning salon. When they’re turned away, they argue over whether they should paint him with shoe polish or bronzer. Luckily for little D.B., The Waitress calls Child Services, who rescues him from their demented clutches.

11 Trying to trigger Ben the Soldier's PTSD

Travis Schuldt as Ben the Solider at Paddys in Its Always Sunny

One of the many recurring victims of the It’s Always Sunny gang, Ben the Soldier becomes a target once again during the ninth season. After Dee and Charlie try and get Ben involved in their pyramid scheme, Mac and Dennis plan to trigger Ben’s supposed PTSD to get him to buy their timeshare. Instead of setting off Ben, they trigger Da’ Maniac, causing him to break a lamp and scare Ben away.

Meanwhile, Dee and Charlie also plan to set off Ben the Soldier by sneaking into his apartment with night vision goggles and torturing him. Seeing as great minds—or in this case, deranged minds—think alike, Dennis and Mac are already at Ben’s bedside, dressed as a couple of Jihadists in fatigues and makeshift keffiyehs. Much to their dismay, Ben informs them he was a computer programmer during the war and never saw any combat. That still doesn’t explain why he dresses like a five-year-old during the day and Ebenezer Scrooge at night, though.

10 Breaking into a house for their version of Extreme Makeover: Home Edition

Rob Elhenney as Mac Kaitlin Olson as Sweet Dee and Danny Devito as Frank in Its Always Sunny

While creating vision boards of all the ridiculous things they want out of life, the It’s Always Sunny gang hatches a scheme to use good deeds to get what they want even faster. Since they had been talking about Extreme Makeover: Home Edition (because Charlie put Ty Pennington’s face all over his vision board), they decided to do their own version for an unsuspecting family.

Taking extreme to another level, they break into the Juarez family’s home with a makeshift wrecking ball. Dressed all in black, looking more like a gang of robbers than anything else, their surprise takeover is like something out of a Rob Zombie movie. With bags over their heads and fear in their hearts, the Juarez family is kidnapped and taken to their Americanized makeover headquarters to await the demolition of their former home.

After smashing and giving away their possessions, threatening them with various weapons, and putting them thousands of dollars in debt, the gang completely destroys the Juarez family’s home. Lucky for them, this is one instance where the gang’s misdeeds actually benefit their victims, as a judge forces Dee to give Frank's mansion to the Juarez’s. If only Ty Pennington could see them now.

9 Impersonating police officers in order to steal from people

Glenn Howerton as Dennis and Danny DeVito as Frank impersonate Police Officers in Its Always Sunny

It all started with a bum masturbating in an alley behind Paddy’s. You know, just a regular day in Philadelphia. After trying (and failing) to find a ‘junkyard dog’ to scare him off, Dennis, Charlie, and Frank buy an old cop car instead. While it would have been enough of a bad idea to just drive around in it, using the sirens to run red lights and cut through traffic, Frank and Dennis take things to another level. To drive a cop car you have to be a cop, right? So they rent police uniforms and impersonate a couple of police officers.

Their crazy idea of justice doesn’t stop there, though. No, they’re determined to get into character. After a hot dog vendor offers them free hot dogs, the power goes to their heads and they start robbing people in exchange for not giving them a ticket. After things start getting out of hand, Charlie becomes the (Al Pacino) voice of reason and finally puts a stop to their shenanigans -- by blowing up the car.

8 Pretending to be crippled to pick up strippers and get free stuff

The gang of Its Always Sunny in Philadelphia gets crippled

Apparently, strippers love guys in wheelchairs, at least that’s what Mac, Frank, and Charlie discover when they go to a strip club. Strippers start fawning over Charlie because he’s in a wheelchair with two broken legs due to Dennis backing over him with his car. They feel so sorry for him they give him a free lap dance, which inspires Mac to get a wheelchair of his own. “People give you free sh** and women treat you like a puppy they just found out on the street,” he tells Dee and Dennis.

So, being the con men that they are, Mac and Dennis head down to the mall in a pair of wheelchairs hoping to score some sympathy. Much to their amazement, Dee already has a scam of her own going, getting guys to like her because of her determination do stuff herself despite having to use walking sticks. As the gang gets bolder in their attempts to use their faux handicaps for personal gain, it all literally comes crashing down around them as Dennis and Mac fall asleep at the wheel and crash into them in front of the strip club. Talk about instant karma.

7 Holding a funeral for Sweet Dee's fake baby to get her out of an IRS audit

Kaitlin Olson as Sweet Dee at fake baby funeral in Its Always Sunny

Sweet Dee’s most horrific scheme all started after she became a surrogate. Instead of just collecting the money and going on her merry way, she decided to try and cheat the system by claiming the baby on her taxes as a dependent. Just like in real life, the IRS came after her sneaky scamming self and slapped her with a big fat audit. Freaking out in normal Dee fashion, she and the rest of the gang concoct an elaborate scheme to stage a funeral for her alleged baby so the IRS couldn’t prove she didn’t have the baby in the first place.

It was a pretty dark thing to do, even for them, but desperate times call for desperate measures. Things were starting to look up for Dee until her eyes started bleeding from the chili powder Dennis blew into them and the funeral became a spontaneous commercial for Wolf Cola. That and the fact that inside the baby’s casket was a very dead and decomposing dog from the alleyway, which Mac and Charlie decided to tip out onto the floor, exposing the charade.

6 Kidnapping, bribing, and molesting a newspaper critic

Charlie Day with Newspaper reporter played by Fisher Stevens in Its Always Sunny

Many a business owner has probably fantasized about doing awful things to the jerks who leave them bad reviews on Yelp or in the newspaper. Luckily for those people, they don’t live in the world of It’s Always Sunny in Philadelphia, where they would clearly never be safe.

When Paddy’s gets a scathing review in the paper, the gang take it upon themselves to find the critic and threaten him into giving them another chance. After he makes it abundantly clear that ain’t gonna happen, Charlie kidnaps and brings him to the bar to be dealt with. Because they taped him to a chair, Charlie and Mac end up helping him go to the bathroom, undoubtedly molesting the poor guy in the process.

Even though they all try and convince themselves they were just ‘borrowing’ him for a couple hours, they can’t leave well enough alone. Amidst trying to make it look like the guy left on a trip, they end up in the wrong apartment and kidnap the owner because he asked too many questions. After ruining not one, but two people’s days, the critic writes additional commentary the next day, which pisses them all off once again. Some people never learn.

5 Pretending to be Jihadists to try and save Paddy's

Rob McElhenney as Mac and Glenn Howerton as Dennis dress as Jihadists in Its Always Sunny

When an Israeli businessman shows up and claims he now owns the land Paddy’s is on, he gives the gang a week to vacate the premises. Always up for a challenge, they first go to a lawyer for advice on how to get this guy off their backs. Since they’re advised there’s no legal way to fight him, they interpret that as a means to get creative and scare him off.

Being the immature man-children that they are, Charlie, Mac, and Dennis start off by toilet papering the building next door—and try to egg it as well. Somehow, things escalate pretty quickly and next thing you know, they’re filming a jihad video dressed like a couple of terrorists. Upon reviewing the tape they actually decide it’s too extreme, which is pretty amazing for them, so they decide to just throw a bag of flaming poop through the window instead.

Because the worst outcome often happens when they’re around, the flaming poop causes the building to explode, destroying the property owned by the Israeli. However, Charlie somehow snuck the video to the guy anyway, causing a couple of police detectives to show up at their door asking questions.

4 Trying to frame Bruce and blowing up a random guy's car in the process

The Always Sunny Gang blows up a guys car

Dennis and Dee’s biological father, Bruce, has pledged to donate all of their mom’s money to an Islamic Cultural Center. Seeing as the apple falls extremely far from the tree, Dee and Frank decide to get revenge since they believe the money should have been theirs in the first place. They plant bomb-making materials in what they think is his apartment so they can frame him and get the money back. Unfortunately for everyone involved, Bruce doesn’t live in a crappy apartment in the middle of Philadelphia.

While scoping out the apartment from the outside, they accidentally crash into the car of the guy who lives there. This becomes a running joke throughout the episode, as the car gets more and more destroyed, eventually blowing up after Charlie cuts the breaks on Frank’s van, which is full of gasoline barrels. Instead of framing Bruce and ruining his life, they destroy this random guy’s car and feel like the a**holes they truly are—for a moment anyway.

3 Making Paddy's an 'anything goes' establishment

Danny DeVito as Frank at a Russian Roulette match in Its Always Sunny

In an effort to show that they won’t stand for limitations on their freedoms, the gang makes Paddy’s an ‘anything goes’ establishment, which opens up a huge can of worms. While Mac and Dennis just wanted to stay open past 2:00 am and have a mardi gras-like atmosphere in the bar, Frank interprets it in a much different way. He invites a bunch of chain-smoking Vietnamese guys to play poker, whose stakes get so high they start betting body parts.

After banishing them to the basement, a new group of crazies shows up at the bar, starting with the McPoyles. Eventually, all sorts of lowlifes and drug addicts wander in, shooting up and drinking themselves stupid. But it’s Charlie bating the McPoyles and getting stabbed with a fork that finally causes them to want to reintroduce rules in the bar. Well, that and the fact that one of the Vietnamese guys kills himself in the basement playing Russian roulette.

2 Getting Rickety Cricket addicted to coke and selling him out to the mob

David Hornsby as Rickety Cricket in Its Always Sunny

Another poor unfortunate soul who consistently ends up in the crossfires of the It’s Always Sunny gang is Rickety Cricket. Aside from all the times they tortured him in high school, more recently, they convinced him to abandon his priesthood and subsequently become homeless as a result. So, when Charlie and Dee run into him on the street while trying to sell some cocaine for the mob, naturally, they rope him into their scheme.

When he sells the drugs lickety split, they convince him to do it again by giving him a little taste of their stash. What follows is a downward spiral into drug-induced crazy that ends up with him unintentionally admitting to something he didn’t do—forcing himself on the wife of the mob boss. “You guys, I did it and I made it so sexy,” Rickety exclaims. Even though he’s talking about the trash can musical he was writing, no one in the gang corrects the mob boss’ assumption, which leads to the destruction of Rickety’s shins.

1 Leaving their enemies to burn in a Thanksgiving Day apartment fire

The Its Always Sunny Gang Squashes Their Beefs

In what was perhaps their magnum opus of extremism and calamity, episode ten of season nine reigns as pretty much the worst thing the gang has ever done. Upon trying to just get the things they want for a non-traditional Thanksgiving, they encounter obstacles at every turn because of the enemies they’ve made. Hoping to squash those beefs once and for all, they invite everyone they’ve been quarreling with to a big Thanksgiving dinner.

Dennis writes up a peace treaty and instead of metaphorically wiping the slate clean and burying the hatchet, they’re prepared to literally do those things as part of a ceremony. However, things don’t exactly go as planned when you’ve got a room full of people who hate each other. As they start admitting to one messed up thing after another, tensions run high and voices are raised, culminating in an epic Thanksgiving food fight.

As the gang regroups, they discover Mac’s room is on fire, the result of an earlier display of beef, where Frank burned a wad of cash. Instead of calling 911, or even apologizing for their misdeeds, they nail the door to the apartment closed and leave all their enemies to burn. Happy Thanksgiving, indeed.


Did we miss any of the gang's worst moments? How much darker can It's Always Sunny really get? Sound off in the comments.

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