The It's Always Sunny In Philadelphia Cast Name The Worst Things Their Characters Have Done

The five Philadelphia-dwelling ne'er-do-wells that call themselves the gang on "It's Always Sunny in Philadelphia" are some genuinely abominable human beings. Over the show's 20 year run, Frank (Danny DeVito), Charlie (Charlie Day), Mac (Rob Mac, formerly Rob McElhenney), Dee (Kaitlin Olson), and Dennis (Glenn Howerton) have done a lot of awful things, ranging from arson to alleged murder. But what do the actors who play the gang think are their absolute worst moments? 

At the 20th Anniversary celebration of the show (as part of The Paley Center for Media's acclaimed PaleyLive series), which was attended by /Film's BJ Colangelo, Day, DeVito, Howerton, Mac, and Olson each shared the things their characters had done that were somehow worse than all of the others. It was a pretty hilarious conversation that must have sounded nightmarish to someone who didn't have the context for each situation. Indeed, despite not really meaning to push the boundaries of comedy (or good taste), the gang has repeatedly toed the line between being seriously funny and potentially offensive.

While some of the actors' answers are pretty easy to guess, like Howerton explaining that "the implication" and especially Dennis' use of it on the cruise ship in "The Gang Goes to Hell" was his character's darkest moment, others are a little more out of left field. Not only that, but the audience apparently had plenty of opinions to offer and shouted them out in an appropriately "Always Sunny" fashion. So, what are the worst things the members of the gang have done in the eyes of the "Always Sunny" cast? Let's take a look.

Day was just as quick and definite in his answer as Howerton, immediately saying that the worst thing Charlie ever did was "the thing to Ruby," which he described as "so ruthless." Ruby (Alexandra Daddario) was Charlie's love interest in the season 8 episode "Charlie and Dee Find Love," but in the end it turned out that he was using her to make The Waitress (Mary Elizabeth Ellis) jealous. He ends up breaking Ruby's heart in a way that feels totally out of character for Charlie, who is never as intentionally cruel or calculating as the rest of the gang. (It's honestly my least favorite episode in the entire series for this reason; Charlie is the secret heart of the gang, and he has to stay somewhat innocent.)

DeVito, on the other hand, claimed that he had never done anything wrong as Frank, to which the audience began shouting out examples of his depravity, including when he tricked Dennis and Dee into digging up their own dead mother to prove he wasn't going senile and could get one over on his kids. Olson, meanwhile, felt that maybe the gang's treatment of former classmate Matthew Mara (David Hornsby), better known as "Rickety Cricket," was by far the gang's worst deed. Since he started the series as an ordained Catholic priest and, as of season 16, was becoming a crime boss of sorts, she's honestly not wrong, though that feels more like an extended situation than a single "worst moment." 

Really, it seems like the folks behind the gang glossed over a lot of things, including some kidnappings, assault, and attempted murder when their characters locked everyone in Mac and Dennis's apartment on Thanksgiving. Then again, the gang has done so many awful things that it's kind of hard to narrow down.

Before Rob Mac even had a chance to answer the question, someone in the audience shouted "blackface" in reference to Mac wearing blackface in the gang's "Lethal Weapon 5" and "Lethal Weapon 6" sequels, the latter of which also features Dee in blackface. The episodes containing said blackface have been removed from some streaming services, along with a few other racially insensitive episodes involving blackface or brownface. Mac, however, was quick to point out that his character had technically gone a step farther by putting blackface on D.B., the infant he and Dee found in a dumpster in season 3:

"We found the baby in the dumpster, yeah, but we were painting the baby, so I actually, not just my own blackface, but painting a child's face, which I haven't seen on Reddit ... that being as much of an issue."

Fans of the "Always Sunny" podcast might remember that Mac occasionally gets a little confused by how the show's subreddit reacts to various things. In this case, he's not defending the use of blackface at all; he's just boggled that people forget that both he and Dee forced blackface upon an infant in an attempt to get famous. Meanwhile, painting his own face seems to get him a lot of hot water, even after the show's creators took full accountability for all of it. Thankfully, the series has a lot more going on than just the gang's terrible antics, and that's helped keep them on the air for all of these years.

Season 17 of "It's Always Sunny in Philadelphia" will premiere on FXX on July 9, 2025, and the next day on Hulu.