You don’t get to 14 seasons without a strong core of a cast. It’s Always Sunny in Philadelphia has that in place with Glenn Howerton, Rob McElhenney, Charlie Day, Kaitlin Olson, and Danny DeVito. Still, one of the underappreciated aspects of the show’s success is the large cast of recurring weirdos that also populate Dennis, Mac, Charlie, Dee, and Frank’s world.
Here are some of the best, most consisten, and outright weirdest supporting characters from It’s Always Sunny’s 14-season run.
Rickety Cricket is the living embodiment of the corrosive effects of the gang’s sins. Once an upstanding young priest named Matthew Mara (and nicknamed Rickety Cricket in high school due to his leg braces), Cricket’s life completely fell apart once he came back into Dee, Dennis, Charlie, and Mac’s orbit. Now he lives on the streets, doing crack, getting into dogfights, and generally just becoming an inhuman monster.
Cricket has appeared in every Sunny since season 2 and you can practically set your watch to how far along the show is by how rough a condition cricket is in.
“In terms of character evolution, [Cricket] really distills so perfectly what this kind of behavior will do to a human being,” Rob McElhenny told us. “So [the Gang] directly, yet in our minds indirectly, affect [Cricket]’s life so much that he goes from a Catholic priest who is very, very happy to a shell of a human being. To watch that devolution of a human at the hands of this behavior, I think really best distills what we’re saying with the show.”
Mary Elizabeth Ellis
The Waitress is another Sunny character who has been around since the show’s very beginning. Originally the object of Charlie’s stalker-ish affection, the still-unnamed waitress has since come into her own. Unfortunately for her, that just means that she’s leaned into her own self-destructive and alcoholic tendencies.
Jimmi Simpson, Thesy Surface, Nate Mooney
Siblings Liam, Ryan, and Margaret love two thinks: milk and making the gang’s life a living hell. The McPoyle family is a largely inbred clan that the gang has known since high school. When Charlie foils a bogus molestation lawsuit the McPoyles have planned, they periodically insert themselves into the Gang’s lives as unibrowed antagonists.
Dennis briefly dated Maureen Ponderosa in high school but found himself turned off by her “dead tooth.” When she turns up in Dennis’s adult life sans dead tooth and bad breath, Dennis almost immediately marries her. After their inevitable divorce, Maureen gets breast augmentation surgery and also begins the process of becoming a human cat. She is now dead.
Chalk Bill Ponderosa up as another man whose life was utterly ruined by a romantic dalliance with Dee Reynolds. Bill was once a fit and attractive young man at the Gang’s high school who settled down into a comfortable life with a wife and children. After Bill and Dee hook up, Bill reveals himself to have a bit of an addictive personality. Now he embraces his full scumbag potential, doing drugs and creeping out women with Frank.
Gail the Snail
Mary Lynn Rajskub
Nobody wants to salt the snail but she gives you no choice. Gail is a universally loathed cousin of Dennis and Dee. She gets by her “snail” nickname honestly, always slurping saliva and displaying a weird phobia of salt. We first encounter Gail during her father’s funeral in season 5. Since then, she’s popped up a few times purely to annoy the Gang.
Ben the Soldier
The Gang first encounters Ben Smith a.k.a. Ben the Soldier when Dee forms an online relationship with him and goes to meet him upon his return to the U.S. When he first appears in a wheelchair, Dee naturally decides to axe the relationship. Turns out that Ben just tweaked his ankle though, costing Dee a relationship with one of the strangest, sweetest doofuses in the Sunny canon. Ben has since guested again on no fewer than four Sunny episodes, always wearing his trademark jean shorts.
Even someone has loathsome as Dee has friends. Well, one friend really. And this one isn’t really a friend. Artemis was first introduced as Dee’s friend from acting class all the way back in Always Sunny season 1. Since then she’s appeared in every season save for 10 and 12. Artemis is, let’s say, sexually adventurous. She is fond of boasting of her “bleached asshole” and has embarked on a truly revolting relationship with Frank Reynolds. Artemis is also an important part of Sunny lore, being the one who translated Charlie’s illegible notes for The Nightman Cometh.
Rex was a contestant to be the model for the Paddy’s Pub billboard but since then has become an object of Mac’s fascination. When Mac fantasizes ascending to heaven and meeting God, it’s Rex who he is in the pearl robes and white beard. When the Gang needs a figurehead for a cult, it’s again Rex who they turn to. Still, despite his Adonis-like appearance, Rex is a very sensitive, vulnerable soul. Dee can bait him into sex with any light level of negging.
Rowdy Roddy Piper
There is not a better match of character and actor in all of It’s Always Sunny than Da’Maniac and Rowdy Roddy Piper (R.I.P., champ). The gang first find retired wrestler Da’Maniac when they try to put on a little wrestling show for the troops. They soon find out that “Da’Maniac” isn’t just a wrestling nickname. Da’Maniac only shows up once more after his initial appearance but those two appearances are so strong that he’s an undeniable force in the Sunny universe. Da’Maniac loves you.
The gang is a powerful force of chaos and the world needs a powerful force of order to keep them in check. Enter The Lawyer – the gang’s most capable nemesis. First introduced in season 3 as the executor of Barbara Reynolds’ estate, the Lawyer periodically turns up on It’s Always Sunny when the gang’s schemes enter into the legal realm. Charlie is passionate about defeating The Lawyer with his knowledge of bird law but The Lawyers usually gets the best of him. Unfortunately, the Lawyer came about utterly defeated and physically disfigured in the grand McPoyle trial so it’s unknown when he’ll come back again.
It’s telling that the gang’s only weapon against the legal prowess of The Lawyer also just happens to be the man who possibly molested Charlie as a child. “Uncle Jack” Kelly is an even worse attorney than he is an uncle, and that’s saying quite a lot. Uncle Jack is very self-conscious about the size of his hands and despite potentially traumatizing Charlie, is increasingly welcome on all the gang’s schemes and trips. He even got a Super Bowl LII invite.
Z is one of Frank and Charlie’s friends from “under the bridge.” He first appeared in season 6 but has since turned up a few more times, typically when there is a party of some sort. He has a deep appreciation for Ben’s jean shorts. He used to have a pair, himself, but he “blew the crotch outta them things.”