The 10 most outrageous moments from It’s Always Sunny In Philadelphia

“Charlie Wants An Abortion” (season one, episode two)

The initial, Danny DeVito-less season saw It’s Always Sunny planting its flag on as many hot-button issues as possible. In this episode, it’s the abortion debate, as the news that Charlie supposedly fathered a child sends him, Dennis, and Mac on their own disastrously self-interested journeys into that particular minefield. The fatherless Charlie’s abortive attempts to bond with the deeply unpleasant child are at least rooted in some sense of personal responsibility, but Dennis and Mac’s infiltration of both sides of the local pro- and anti-choice ranks is motivated purely by their desire to get laid. And while Mac successfully lures a rabid activist into a handy backseat (by hinting at his nonexistent role as abortionist-murdering zealot), her subsequent pregnancy announcement sees him immediately urging the young woman right into the very women’s health clinic they’d been picketing.

“The Gang Finds A Dead Guy”/“Pop-Pop: The Final Solution” (season one, episode six/season eight, episode one)

The running joke of Dennis and Dee’s decrepit grandfather having been a full-on Nazi is never meant to explain why the Reynolds siblings are the way that they are. In fact, the Gang is horrified at the revelations in these episodes that their semi-beloved Pop-Pop is a racist monster, that they were whisked off to Hitler Youth day camp without realizing it, and that Pop-Pop’s storage unit may be home to some of failed painter Hitler’s lost artworks. (Rejecting Nazis is a low bar, but credit where it’s due.) After trying to hawk the old man’s memorabilia to a horrified museum curator, Mac and Charlie ultimately decide to just burn it all behind Paddy’s (and hit Dennis with the news of his grandfather’s evil, just for fun). Still, trafficking as these linked episodes do in both Nazi regalia and the dying Pop-Pop’s vituperative racism is queasy stuff, with only the Gang’s collective no-win fates assuring viewers that Nazism doesn’t pay.

“The Gang Finds A Dumpster Baby” (season three, episode one)

Sometimes a tableau only tells part of the story. Sure, “The Gang Finds A Dumpster Baby” ends with a social worker coming upon the titular abandoned baby in blackface, seemingly about to be bisected by Charlie, Frank, and Dennis with a scimitar. But it’s the journey—child endangerment, exploitation, and neglect—that lends that final shot such comedic power. Finding an adorable infant behind Paddy’s, the Gang’s first instinct is to re-abandon the tyke, only for Dee and Mac to imagine a life as lucrative stage parents.

Meanwhile, Charlie finally pries from Frank and his mother the fact that he himself wasn’t so much abandoned as deliberately but incompletely aborted, with Frank refusing to acknowledge Charlie as his son. After finding out that white babies aren’t what advertisers are looking for these days, Dee and Mac unsuccessfully try quick-tanning the kid before whipping out the shoe polish, while the arguing Frank and Charlie fight over the shiny “Ali Baba sword” they found in their nightly dumpster-dives. And that’s where we came in, not having even mentioned how Dennis deceived a comely environmentalist into sex while ensuring the razing of an entire forest.

“Mac Is A Serial Killer” (season three, episode 10)

When the big reveal of a refrigerator full of multiple severed human heads isn’t the most upsetting thing in an episode, you know It’s Always Sunny is going for broke. Here, Mac’s suspicious absence from Paddy’s prompts the Gang to connect him to a string of serial murders, leading to an elaborate To Catch A Predator sting where they attempt to get their friend to confess to being an actual, head-chopping predator. And while the final reveal suggests that Frank, packing a chainsaw for maximum vigilantism, enacts gory justice on the actual killer, it’s the revelation that Mac’s been sleeping with transgender woman Carmen (Brittany Daniels) that truly upsets the Gang. An act both his Catholic guilt and fragile macho image condemns to secrecy, Mac’s seasons-long attraction to the proudly trans Carmen routinely sees the Gang referring to her with an offhand trans slur. Glenn Howerton apologized in a later interview, noting that, unlike in later seasons, no member of the Gang piped up to even performatively object to the slur in order to make one of the others feel bad.

“The Gang Buys A Boat” (season six, episode three)

It’s Always Sunny seeds possible motivations for the Gang’s individual awfulness throughout its run, without ever positing those events and influences as sufficient excuse. Dennis, for example, might have been molested by his Rick Moranis-looking female school librarian as a young teen (an event Dennis steadfastly maintains is both no big deal and evidence of his sexual prowess), but that in no way explains how elaborate and merciless his own sexual practices are. Here, cornered by a confused and increasingly alarmed Mac about his enthusiasm for purchasing a run-down houseboat, Dennis’ explanation of “the implication” that will prove the deciding factor in stranded-at-sea women’s choice to succumb to his will is one of the most succinctly creepy moments in TV history. The way Howerton makes Dennis’ eyes go black as he freezes Mac with his imagined narrative of very, very dubious consent encapsulates Dennis Reynolds’ inner darkness more than his trunkful of zip ties and duct tape.

“Frank’s Pretty Woman” (season seven, episode one)

The addition of Danny DeVito as Dennis and Dee’s rich and hedonistic father Frank saved It’s Always Sunny from cancellation. It also introduced Frank’s more retrograde, old-school awfulness to the rest of the Gang’s more complexly self-delusional mix of rationalization and tortuous justifications.

Here, Frank’s plan to marry sex worker Roxy (Alanna Ubach) sends the rest of the Gang scrambling, not so much out of concern, but because the whole thing is sort of gross and embarrassing to them. Frank’s blunt bigotry and misogyny is a tricky tool to work with, and there are times here when his disregard for the women in his life reaches unsettling depths. But no Sunny ending is more jaw-droppingly, go-for-broke insensitive than when Frank, finding that Roxy has overdosed right before their ceremony in his and Charlie’s filthy apartment, urges the Gang to just drag her body into the hallway. Frank, noting that that’s what Roxy would have wanted, walks off, as Roy Orbison’s “Pretty Woman” plays over the spectacle of the woman’s splayed and lifeless body.

“PTSDee” (season seven, episode 12)

There’s nothing more triggering to a member of the Gang than when someone dares to suggest that their personal awfulness is worse than the Gang’s collective awfulness. So when Dee finds out that the male stripper she slept with the night before considers her his “rock bottom,” she hatches an elaborate scheme to prove she, instead, rocks.

Luring her depressed conquest back to his abandoned stripper life with a triumphant comeback show at Paddy’s, it’s finally revealed that the young woman he’s been enthusiastically grinding on is in fact the daughter whose estrangement had contributed to his downward spiral into Dee’s bed. Sweet Dee’s perpetual marginalization makes her the victim more often than anyone in the Gang, but, when roused, she can enact truly terrifying vengeance. Here, crowing in magnificent villainy, “That’s your rock bottom—you sticking your dick in your daughter’s face, you son of a bitch!”, Dee shows herself to be as capable of wrecking lives as the guys should anyone set her off. When a shocked Dennis calls Dee’s manipulation the darkest thing she’s ever done, it’s with admiration as much as horror.

“Charlie And Dee Find Love” (season eight, episode four)

As comparatively endearing as Charlie Kelly can be, It’s Always Sunny never lets us forget the depths of his obsessive neediness, and how much damage he can do because of it. In this season eight episode, a chance car accident sees Dee and Charlie both wooed by a pair of ultra-rich Philly elites. Trevor Taft (Joshua Thomas Casaubon) turns out to be just the sort of douchebag frat boy you’d expect Dee to run afoul of, the episode’s denouement reveals the Taft family’s rich and beautiful daughter, Ruby (Alexandra Daddario), has actually fallen hard for Charlie, his ravenous cheese hunger and position as Paddy’s designated rat-dispatcher notwithstanding.

Charlie’s series-long obsession with Mary Elizabeth Ellis’ deeply uninterested Waitress appears over, but as soon as he finds out she needs him again, Charlie deliver a stinging rebuke to the one woman who actually seems to reciprocate his love. Charlie (tinkling music mockingly scoring his tirade) tells Ruby icily, “You slept with me almost instantly—and by the way, a quality woman doesn’t do that. She doesn’t say yes right away, she says no to a man, for years, like, 10 years.” Charlie is as damaged as any character we’ve ever seen, but that doesn’t mean he’s safe to touch.

“The Gang Turns Black” (season 12, episode one)

The season 12 opener not only sees the Gang awaken transformed into Black versions of themselves—played, this time, by Black actors and not the Gang in blackface. It’s also a musical episode, with the Gang fumbling their way through the Philly streets as they attempt to figure out how they got this way (and, to their increasing panic, how to turn back).

As daring and ultimately successful an exercise in It’s Always Sunny’s sneakily insightful examination of the blinkered state of American racial politics, the true shock isn’t in Frank’s predictable reaction to seeing the world as a Black man (he really, really wants to say the n-word), but in the episode’s bloody and genuinely heartbreaking conclusion. Charlie, the one Gang member whose alter ego is a child (AJ Hudson), assures his friends that a carload of armed police summoned by a jittery shop owner are there to help, only for the toy train in his hand to be confused for a gun. Even if the episode turns out to be a brain-fried dream of Carl (Wil Garret—who’s mostly known as the Old Black Man on the show), the lightning-quick edits of the young Hudson’s chest exploding from the cops’ bullets slams the episode’s message home with a sickening, blood-red clarity. The Gang doesn’t ever learn, but that doesn’t mean It’s Always Sunny isn’t occasionally and shockingly illuminating.

“Mac Finds His Pride” (season 13, episode 10)

The real shock here comes from an act of elaborate and lovely sincerity. Mac’s tortured acceptance of his own, deeply repressed homosexuality has long been treated as a joke, both by the Gang and the show. For the Gang, Mac being gay is just another thing about him they don’t give a shit about, while, for the show, the gyrations of a shame-warped closeted gay man lashing out in every direction makes for good comedy. The last five minutes of season 13 see Mac telling his terrifying incarcerated father, “Dad, I’m gay,” before revealing the starkly impactful interpretive dance routine he’s been working on all season as he worked through his decision, largely offscreen.

We saw how Rob McElhenney had sculpted Mac’s body this season as inexplicably as he’d packed on the pounds prior to season seven, and now we see why. The episode up until this point had been a tiresome rehash of “Mac is gay” jokes from the Gang, all of which, here, turn out to be a grand fakeout to set us up for one of the most lovely and wrenching five minutes in the series’ history. Viewers were torn, arguing whether the show’s eternal commitment to illuminative comic cruelty could shoulder something so heartfelt. In the end, it’s Frank, of all people, who gasps out an awed, “Oh my God. I get it. I get it.” In that moment, we are Frank, and Frank is us. You never know just how or when It’s Always Sunny In Philadelphia is going to sucker-punch you, and leave you gasping.