The Worst Things The Always Sunny In Philadelphia Gang Have Ever Done

The misanthropic sitcom "It's Always Sunny in Philadelphia" has officially become the longest-running comedy series in the history of American television. Created and produced by Rob McElhenney, Glenn Howerton, and Charlie Day, the adventures of the so-called "Gang" have long been beloved by critics and fans alike. In December 2021, Howerton even told "Late Late Show" host James Corden that it's basically impossible for him to walk around Philadelphia itself without being set upon by fans of the show.

Arguably the most endearing aspect of "Always Sunny," of course, is its wholehearted commitment to total depravity. The Gang's schemes tend to be opportunistic at best and outright psychopathic at worst, and over the course of the show they've indulged in tax fraud, arson, kidnapping, assault, and even murder — if you believe the fan theories, that is.

Here's a question, though: what are the very worst things the Gang have ever done? It seems that not an episode goes by without Dennis, Mac, Charlie, Dee, and Frank doing something truly horrendous, but, when you're looking at more than 162 episodes of the show, it can be pretty difficult to pin down the most abhorrent of them all. Luckily, we've got the low-down on the lowest deeds committed by everyone's favorite miscreants. These are the worst things the "Always Sunny in Philadelphia" Gang has ever done.

No episode sums up the utter wickedness of the Gang better than Season 7's "Sweet Dee Gets Audited," the climactic scene of which provides one of the show's most macabre moments. The basic gist of the story is that Dee finds herself audited by the IRS after claiming a baby (that she had previously birthed as a surrogate mother) as her dependent. Meanwhile, Frank tries to distance the bar's dodgy dealings from the impending audit while Dennis, Mac, and Charlie inadvertently form a microcosm of America's political system. It's a whole thing.

In the end, the Gang decides that there's only one way they can possibly throw Dee's snoopy IRS agent off her (and the bar's) trail: staging a fake funeral for the baby. Even the members of the Gang themselves are aware of how messed up this is, with Dennis pointing out beforehand that this is "easily the darkest thing we've ever done."

It goes about as well as you might expect. Dee ends up bleeding from the eyes when Dennis blows chili powder in her face to help her cry, while Frank gives a eulogy that ends in an advertisement for his fake soda distributor "Wolf Cola." As for Mac and Charlie — well, after correctly suspecting that Frank is up to something shifty, they expose the dummy funeral to the IRS agent and tip what they believe is an empty coffin onto the floor ... exposing the rotting corpse of a dog that had died in the alleyway outside. All in all? Not their finest hour.

Over the years, the Gang has produced, directed, and starred in a number of unofficial installments in the "Lethal Weapon" series. In a move that can only be described as deeply unfortunate, the Gang has also taken these opportunities to dabble in blackface.

"Lethal Weapon 5" first appears in Season 6's "Dee Reynolds: Shaping America's Youth." In this episode, Dennis is quick to point out that Mac's use of blackface during his performance as Murtaugh is racist, while Mac argues that it's a time-honored dramatic tradition (Frank, true to form, claims that it's acceptable, just so long as it's funny). In the show's ninth season, "The Gang Makes Lethal Weapon 6" returns to the subject; this time, however, now Mac and Dee wear blackface.

Times have changed since then, of course, and the show took a somewhat meta approach to discussing these past misadventures in the Season 15 episode "The Gang Makes Lethal Weapon 7." During this episode, the Gang hears that their previous "Lethal Weapon" movies have been pulled from the local library for their offensive nature — the same fate that befell the "Lethal Weapon" episodes in 2020.

In Dennis' words, however, the Gang has done "a lot of learning, a lot of growing, and a lot of being scared" in recent years, so they decide to make the third in their homemade trilogy, this time starring two Black actors. One of those actors is a Donovan McNabb impersonator and the other is a literal pimp — but hey, progress is progress.

Dee Reynolds is by far the most put-upon member of the Gang. Although she's no angel herself, Dee has been subjected to endless abuse, mockery, and even assault during her time working at Paddy's Pub. Perhaps the cruelest thing the other members of the Gang have inflicted on Dee, however, is success.

In Season 9's "The Gang Broke Dee," Dee finds herself hauled from rock bottom into the spotlight after the rest of the Gang, worried that they might have been "in some ways responsible" for her sorry state, suggest she channel her misery into stand-up comedy. After delighting the crowd at an open mic night with her self-deprecating humor, Dee finds herself launched into superstardom. She attracts a talent scout named Snyder, scores a number of huge gigs, and even books a slot on "Late Night with Conan O'Brien. " Of course, she's also more than happy to leave the rest of the Gang in the dust, including an increasingly baffled and frustrated Dennis.

As Dee steps out onto the stage to meet Conan, however, the episode pulls a brutal twist: everything that had previously happened to Dee had been set up by the Gang, who hired dozens of actors to convince Dee she'd made it in showbiz. They did this, apparently, to prove that she could sink lower than rock bottom (and as punishment for joking earlier about suicide). Just for added flair, Mac, Charlie, and Frank had chosen not to let Dennis in on the scheme, driving him to the brink of insanity too. Talk about two birds and one stone.

In the Season 4 episode "Paddy's Pub: The Worst Bar in Philadelphia," the Gang receives some bad news: a local newspaper critic has given them a shoddy review. The critic in question, Harvey Korman, complains about the bar's lack of charm, Dee's crass insults, and the ceaseless arguing of the three "classless bores" who own the place.

The Gang responds to this criticism with all the grace you'd imagine, visiting Korman's office, threatening him, and taking a hammer to his belongings. But it's Charlie who takes things a step too far when, unable to let his hatred of Korman go, he kidnaps the critic and brings him to Paddy's Pub. Worried about the litigious consequences of Charlie's crime, the rest of the Gang decides to commit to the kidnapping and try to get a better review out of Korman. Over the next few hours, Korman is tied up, insulted, and knocked unconscious by Charlie, while Dennis and Dee somehow end up kidnapping Korman's cat and neighbor.

The Gang has kidnapped a number of people in the years since "The Worst Bar in Philadelphia," be it accidentally or intentionally. But Korman's case might be the most disturbing of all — not only because it ends up in a double kidnapping (or triple, if you count cats), but also because there's no way of telling just what Charlie might have done to Korman had the others not been around.

It won't come as much surprise to hear that the Gang has made plenty of enemies over the years. Their reckless plans and gung-ho nature has ticked off all kinds of people, and in Season 9's "The Gang Squashes Their Beefs," they try to bring some Thanksgiving cheer to the people they've wronged ... mostly because these beefs have finally begun to inconvenience them.

Naturally, things quickly take a dark turn. The guest list at the Gang's beef-squashing party, which is held in Dennis and Mac's apartment, includes the McPoyle brothers, Frank's landlord, Gail the Snail, a random man whose car was destroyed by the Gang years earlier, Bill Ponderosa, and Rickety Cricket, who shows up uninvited. Before long, the McPoyles are clamoring for Frank's eye, Bill, Frank, and the random guy are high on cocaine, and a vicious food fight has broken out. Worst of all, though, is the "money fire" that Frank started earlier, which, by this point, has totally engulfed Mac's room.

As the fire spreads and the party descends into chaos, the Gang chooses to flee into the hallway, locking the door behind them and trapping their enemies inside. Frank's casual prediction that they'll all burn to death is dismissed by Dennis, who points out that there's a fire escape inside the apartment — but nevertheless, this is a pretty clear-cut case of attempted murder. Luckily, only Cricket ends up worse for wear.

Not every awful thing the Gang has done happened out of malice. Being who they are, things can get out of hand even when they're trying to do the right thing, and there's no better example of this than the Season 4 episode "The Gang Gets Extreme: Home Makeover Edition."

Off the back of a recent obsession with "Extreme Home Makeover," the Gang decides to gain a little karma by recreating the show (in which families that have fallen on hard times are given a drastic makeover of their homes) for an immigrant family that lives down the street. They begin by kidnapping the Juarez family in the middle of the night, blindfolding them, and taking them back to the bar, where Dee's broken Spanish convinces the three Juarezes that their "life is no more." Just for good measure, they force Mr. Juarez to pay for all the construction materials before subjecting the whole family to "good old-fashioned American cinema" (Mel Gibson's "Apocalypto") and an all-American fashion makeover. Meanwhile, the construction crew — Frank, Dennis, and Charlie — mess about with a wrecking ball, bicker among themselves, and eventually burn the Juarez family's house to the ground.

Funnily enough, this is one of the very few instances in the whole run of "Always Sunny" in which the Gang are actually held accountable for their actions, as a court awards Frank, Dennis, and Dee's childhood mansion to the Juarez family. As Mac so succinctly puts it: "You try to help people, and you just wind up getting screwed."

Gather ye round, children, for this is the tragic tale of Rickety Cricket. Quite rightly described by AV Club's Dennis Perkins as "the Gang's 'Picture of Dorian Gray,'" the ex-priest known as Matthew Mara is a walking, talking representation of the corrupting influence of Dennis, Mac, Charlie, Dee, and Frank.

In "The Gang Exploits a Miracle," his first appearance on the show, Mara is a mild-mannered priest with a crush on Dee Reynolds; a dozen seasons later, he is a traumatized, disfigured, homeless crack addict with absolutely no qualms about what he'll do for a case of beers. Over the years, Cricket has been used as a drug mule, hunted for sport, wounded by a stray trash can, struck with a hatchet, shot in the hand, and much, much more — and even if the Gang doesn't actively participate in Crick's misfortunes, it's usually involved in them in some way or another.

Oddly enough, by the show's later seasons, Cricket appears to have settled into his role as the Gang's "street rat," showing much more enthusiasm for their schemes and often stopping by Paddy's to smoke PCP in the bathroom. In the Season 12 episode "A Cricket's Tale," he even turns down a golden opportunity to get his life in order, instead choosing to remain with the Gang. It's actually almost sweet ... you know, if you ignore all that other stuff.

You'd hope that any decent human being would try to help you if your life was in danger, and you'd certainly hope that your friends and family would do the same. Then again, the Gang aren't decent human beings — so maybe it's no surprise that, in Season 14's "The Gang Chokes," every last one of them leaves Frank to die when he chokes on an appetizer in a restaurant.

In fact, the show makes a point of showing each member of the Gang's expression as they watch Frank struggle. Charlie, who later admits that he was mad because Frank interrupted his speech, hesitates a little too long; Mac looks to Dennis for a cue but receives none, and so refuses to get involved; Dee quite genuinely looks like she's rooting for the appetizer; and Dennis watches on with the exact kind of utter vacancy you'd expect from a diagnosed sociopath. Luckily for Frank, the recurring character known as the Waiter saves him in the nick of time.

Now, Frank's relationships with the other members of the Gang have hardly ever been ideal — with the notable exception of Charlie, of course — but allowing him to choke to death still seems pretty harsh. And this isn't the only time the Gang has put Frank's life in danger.

During the Season 10 episode "Frank Retires," Frank (you guessed it) retires. This immediately kicks off an epic political showdown between the various members of the Gang for total control of Paddy's Pub, of which Frank had previously been majority shareholder.

Oaths are sworn, backs are stabbed, and world-shattering revelations come to light, but among it all, one thing remains constant: Frank just keeps on losing blood. Charlie is first to drain Frank in an attempt to prove that they're father and son, but the doctor they harass into performing the DNA test points out that the bucket they used to collect it was contaminated with the blood of four more individuals and one animal. Later, Dee joins up with Charlie, and the two of them try to secure more blood from Frank by filling up a plastic bag. Then, during the final showdown between each member of the Gang, Mac turns up with his own bottle of Frank's blood, because he feels "like we're probably gonna use it in the future and he was already opened up."

Considering the doctor approached by Charlie tells him that Frank was likely "in desperate need of blood," it's probably fair to say that two more impromptu donations didn't do Frank much good. Sure enough, by the end of the episode, Frank is, in his words, a "shell of a man he once was." He then decides that retirement is bad for him and announces his return to Paddy's Pub, none the wiser to the fact that his closest friends were behind his rapid decline in health.

Ben the Soldier is one of the few wholly "good" recurring characters to feature in "Always Sunny." Unfortunately, this makes him a prime target for both Dee's predations and the Gang's sordid schemes.

The most brutal example of this takes place in the Season 9 episode "Mac and Dennis Buy a Timeshare," in which various members of the Gang attempt to exploit Ben's PTSD in order to hook him onto a scam. Having been tricked into joining a pyramid scheme aimed at selling stress-reducing berry juice, Dee and Charlie try to convince Ben to join in by breaking into his apartment wearing night vision goggles; the idea is to trigger Ben's shellshock in order to make him more susceptible to their demands.

When they arrive, however, they find Dennis and Mac have already beaten them to it, dressing as Arab terrorists and forcing Ben to watch war movies in an effort to get him to buy into their timeshare. At that point, Ben reveals that he doesn't actually have PTSD, and that he served in the army as a computer programmer. This was actually Ben's last appearance in the show to date, so it can only be assumed that the Gang gave up on him as soon as they realized he was pretty much immune to manipulation.

In case you ever needed proof that the Gang's atrocities stretch back as far as "Always Sunny" goes, the show's third-ever episode, "Underage Drinking: A National Concern," finds Paddy's Pub blighted with underage drinkers — and the Gang leaping to capitalize on them.

When they first realize that the bar is filled with underage teens, the Gang decides that they have a civic responsibility to provide a safe space for them to drink. It takes practically no time at all for Dennis, Charlie, Mac, and Dee to become fully embroiled in the lives of these kids, however, and the Gang even ends up hosting a pre-prom party at Paddy's.

Now, plying children with alcohol is one thing (even if it is watered down,) but Dee really outdoes herself in "Underage Drinking." Embittered by her own failed high school career and encouraged by the advances of a popular jock, Dee agrees to go on a number of dates with him, essentially courting an underage boy. It's an early yet significant low for Sweet Dee, and one that, unfortunately, would be repeated in the years to come.

Season 14's episode "Paddy's Has a Jumper" begins with the Gang discussing the power of algorithms to decide how people should act and behave, mostly in the context of binging TV shows on streamers. Before long, however, the Gang is applying their own algorithm to a life-or-death situation: namely, the fate of a suicidal man who is threatening to jump from their roof.

It should go without saying that Dennis, Mac, Charlie and Dee's careful investigation into the man is incredibly callous; they ask whether the man could die, whether he would actually jump, and whether they should let him. They even conclude that the man's death would be best for everybody involved, suggesting that the bar could become a suicide-themed tourist attraction. The Gang then actually commits to this man's death, insisting that they give him a helping hand, all in the name of the algorithm (as Dennis says, it's best to think of it as more of a "deletion" than a murder).

Mercifully, the jumper is accidentally tricked into coming down by Frank, whom he believes is his estranged father. Although the man is clearly disappointed to find this isn't the case, it's probably for the best that he made that mistake.

The worst thing to happen in Season 10's "Mac Kills His Dad" isn't actually Mac (very nearly) killing his own father — in fact, this particular crime takes place in the story's B-plot. When Frank's friend and Dee's ex Bill Ponderosa arrives at the bar to cheerfully announce a decision to drink himself to death, Dennis, Dee, and Frank try to show him that life is worth living. Pondy, however, is too far gone and seems determined to check out on his own terms, and so the trio pivot to a new plan: take out a life insurance policy on him and cash in when he dies.

At the same time, Mac and Charlie discover that Mac's father, Luther, is facing the death penalty for a crime he didn't commit. Bill subsequently volunteers to confess so he'll be executed instead, allowing the Gang to cash out while Luther can walk free. Fortunately, or unfortunately (who can tell anymore?) Bill has a last minute change of heart, decides that life is good, and rats on the real killer instead — dooming Luther to an inevitable prison shanking.

One other moment in this episode deserves a shout-out, too: Frank's go at cheering up Bill, in which he explains the thing that makes him happy is riding around town in a limousine, filling a balloon with champagne, then throwing it in the face of a homeless man to give him a "taste of the good life." Even for Frank, that's pretty dark.

The final moments of Season 13's "The Gang Gets New Wheels" mark a truly shocking chapter in the Gang's history of depravity. Earlier in the episode, Charlie and Mac had bought some new bikes before being bullied by a gang of local kids; Frank had struck up a friendship with a teenage boy at driver's ed, who he promises to help score with a woman; Dee, meanwhile, had befriended a clique of local mothers, one of whom she suddenly turned against after being casually insulted.

Dennis' (far less scandalous) subplot ends with him regaining the exact type of Range Rover he had previously lost when the Gang destroyed it with an RPG in "Dennis' Double Life." He then takes his car around the city, picking up each member of the Gang as they flee the consequences of their own storylines: Charlie and Mac have violently assaulted the children who bullied them, possibly killing at least one, while Dee has slept with her enemy's "boy-toy" to get her own back — unfortunately, he has turned out to actually be the woman's teenage son and the boy that Frank had befriended. In the space of a few minutes, Charlie and Mac have murdered a child, Frank and Dee have inadvertently conspired in the statutory rape of a teenager, and Dennis has helped them all make a quick getaway. It really doesn't get much more messed-up than that.