The Worst Thing Every ‘It’s Always Sunny…’ Character Has Ever Done

5 Charlie: Faking Cancer (Season 1, “Charlie Has Cancer”)

After everything the Gang has done over the years, Charlie’s (Charlie Day) worst moment goes all the way back to the pilot, which was made with a few bucks and a dream — a dream of a show in which an asshole fakes having cancer to get a date.

In what’s still one of Charlie’s most elaborate plans, he tells Dennis (Glenn Howerton) he has cancer so that Dennis will tell The Waitress (Mary Elizabeth Ellis), and she’ll agree to go out with him. Of course, Charlie’s friends aren’t exactly victims here since they end up using Charlie’s cancer to garner secondhand sympathy and have sex with other women, including The Waitress. As for The Waitress herself, she did have to put up with Charlie for a day, but at least she got $250 and some Dennis action out of it. 

Five years later, Charlie’s mom (Lynne Marie Stewart) pulled a similar stunt when she pretended to have cancer to raise money to fix a Virgin Mary statue she ran over. When Charlie asks where she got the idea, she says, “I learned it by watching you.”

Matthew “Rickety Cricket” Mara (David Hornsby) has to be the worst casualty of the Gang’s depravity, having gone from a fresh-faced priest to a badly-scarred, drug-addicted homeless man who openly shacks up with dogs throughout the series. And it all started with Sweet Dee (Kaitlin Olson), his high school crush, who once promised she’d kiss him if he ate a turd, then turned him down because, well, he ate a turd.

When they meet again in adulthood (or what passes for adulthood in this show), Dee seduces Cricket while trying to get him to bless a water stain shaped like the Virgin Mary. After some initial resistance on his part, she convinces him to quit the priesthood, only to turn him down again when he does.

A year later, Dee gives Cricket another little push toward corruption when she and Charlie get him addicted to drugs so that he’ll help them sell some on the streets that he now calls home. After that, Cricket didn’t really need any more assistance from the Gang on his journey to monsterhood, but they still help him every once in a while because they’re nice like that.

3 Mac: Feeding His Dead Dog to Dennis (Season 11, “Mac & Dennis Move to the Suburbs”)

One of the most tragic characters in this series is little Dennis Jr., the dog Dennis buys Mac (Rob McElhenney) when they move to the suburbs together. But what begins as a happy family slowly devolves into a living nightmare as Mac and Dennis start losing their sanity due to the unnatural isolation of suburban life. Sadly, or perhaps mercifully, the “living” part doesn’t apply to Dennis Jr. for too long since the increasingly deranged Mac neglects the dog into an early grave. He then goes full Titus Andronicus, mixing Dennis Jr.’s body into a plate of his “famous mac and cheese” and feeding it to Dennis Sr.

Oh, and it wasn’t even his famous mac and cheese — it was store brand. And they say Dennis is the psychopath.

2 Dennis: Talking a Man into Setting Himself on Fire (Season 10, “Mac and Charlie Join a Cult”)

In the “Ass Kickers United” episode, Dennis, Dee and Frank (Danny DeVito) start a fake cult and compete to see who’s the best at manipulating its members, which include Mac and Charlie. Frank convinces someone to eat a turd sandwich (in case you had any doubt who raised Dee), Dee gets the cultists to rebuild Dennis and Mac’s burnt-down apartment while making them think they’re going to another dimension, and Dennis tells them to kill themselves. As they’re arguing over who’s the winner, one of the cultists actually lights himself on fire on Dennis’ orders, thus re-igniting the apartment. 

Note: The first time the place burned down was due to the Gang’s botched Thanksgiving dinner, which ended with them trapping all their enemies in the apartment as it was engulfed in flames, also on Dennis’ suggestion. 

Determining Frank Reynolds’ lowest moment is a challenging task. Is it his dealings with Jeffrey Epstein? When he opened a Vietnamese sweatshop “a lot of good men died in,” by his own admission? The time he pimped out his son? The time he waterboarded his daughter? When he set her on fire? All those times he gleefully ruined Christmas for them over the years? 

We could do this all day, so let’s limit this to reprehensible things we’ve actually seen Frank do in the show. In that case, the winner has to be the time he went to the trouble of hiring a fake psychic and burying money in a dog’s grave to manipulate Dennis and Dee into believing that their mother was still alive and had hidden millions of dollars all over town, including in her supposed coffin. When the Gang cracks open the casket, expecting to find a fortune inside, Franks laughs his ass off as his kids scream at the sight of their mother’s actual remains. Even Dennis seems to think this is going too far, judging by his traumatized weeping.

So there you go: Every character in this show is definitely going to hell, and so are all of us for enjoying it. Hope they don’t serve mac and cheese there.  

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