Starting with its second season, It’s Always Sunny in Philadelphia has focused on five characters: Dennis, Mac, Dee, Charlie, and Frank. But since the show has aired over 100 episodes, a few tag-alongs have been picked up along the way.
There are characters who started off as one-off parts or guest stars who ended up coming back again and again, either because they were hilarious or because they struck a chord with fans. Now heading into its 14th season, It’s Always Sunny has built up a respectable cast of supporting characters. So, fans of It’s Always Sunny, here is Every Supporting Character, Ranked.
Ben Smith – also sometimes known as Ben the soldier – is not a particularly funny or interesting character. He’s depicted as a total dumbo who could be manipulated by Dee. His introduction in “The Gang Wrestles for the Troops” led to one of the best episodes of the series, and he played an important role in “The D.E.N.N.I.S. System,” but ever since then, his recurring appearances have had diminishing returns.
His characterization seems to get weirder and weirder – like how he always wears cutoffs and he sleeps in Scrooge-style pajamas – and along with that, he becomes a less and less enjoyable part of the show.
Bill Ponderosa is even more of a degenerate than anyone in the Gang. He’s even further off the deep end than Frank, who is his terrible A.A. sponsor. While Lance Barber plays the depravity of Bill well, the character just goes too far sometimes.
If all he does is snort cocaine and he puts a gun to his own head every five minutes and he constantly cheats on his wife with prostitutes, then he’s too debauched and corrupt to be funny. Barber finds himself too busy playing Bill as an uncontrollable drug addict to make anything he’s doing actually funny.
The McPoyles have been in the show since its first season. They’re among the oldest characters on the show. They’ve been involved with the Gang longer than Danny DeVito’s Frank Reynolds. Unfortunately, as gross as they are, that doesn’t really translate into comedy.
We can get some laughs out of the Gang’s reactions to their disgusting behavior – like how they always drink milk and have a “pure” bloodline – but on the whole, they’re not great characters in and of themselves. Still, it’s impossible to deny what a joy it is to see Guillermo del Toro play their insane, grubby patriarch.
Everything about Maureen Ponderosa is both weird and hilarious. When we met her, she was defined by her dead tooth and her cat sweaters. But when she died sometime before the events of “Making Dennis Reynolds a Murderer,” she was defined by the fact she had transitioned into a cat.
She had surgical procedures to become a cat, because that was how she identified. Her character developments were always very interesting, but the way she was portrayed on the show never matched it. It’s funnier to think about her character than it is to actually watch her in an episode.
Artemis’ role in It’s Always Sunny has changed a lot over the years. She was introduced as Dee’s actor friend, but she later became Frank’s “booty call” and helped to make Charlie’s Nightman Cometh script more legible (by adding words). She also went on a date with Ben the soldier after his wheelchair made Dee uncomfortable.
When it turned out to be from a twisted ankle and not a permanent disability, Dee wanted him back and Artemis wasn’t having it. She is played by Artemis Pebdani, who Mary Elizabeth Ellis (the Waitress) knew from their performance group “Discount Cruise to Hell.”
Charlie’s creepy uncle Jack Kelly is not only a terrible attorney who folds under pressure, he’s also in possession of some incredibly illegal images that he defends as art, he may or may not have molested Charlie as a child when they shared a bedroom, and he is perpetually fretting about the size of his hands.
It’s not easy to make a character like this likable, and Andrew Friedman doesn’t necessarily do it, but he does succeed at making Uncle Jack an endearing character. He plays the role as suitably pervy, but he’s also very watchable and very funny in the role.
The cast of It’s Always Sunny have often said that Charlie’s genuine unrequited love for the Waitress is one of the things that makes the Gang endearing, as opposed to just terrible. Most fans know that Mary Elizabeth Ellis, who plays the Waitress, is married to Charlie Day in real life, which makes their whole back-and-forth in the show seem less creepy and mean-spirited.
It helps to make the stalking more palatable. Either way, the way Charlie and the Waitress’ relationship has developed over the years, like when Charlie finally got her to date him and instantly became bored with her, has been really interesting.
When Rickety Cricket first got involved with the Gang, he was a priest. Now, he’s a homeless drug addict covered in scars and burns who has to fend off stray animals in the night and had a romantic relationship with a dog. It’s Always Sunny uses Cricket just the right amount.
He comes back often enough to be classed as consistently funny, but not so much that the joke gets old. It’s always surprising to see how much worse he’s gotten as the seasons go by, and it is always a joy to see him come back to Paddy’s Pub.
This character has never actually been named, although he has appeared on the show a bunch of times. The Gang just never bothered to learn his name – they’re more interested in using his legal services for free. As a result, he’ll take on any case in which he’ll get to prosecute them, pro bono, whether it’s Dennis’ divorce settlement or placing blame in the McPoyle/Ponderosa wedding massacre.
If he’s not getting screwed by the Gang, he’s figuring out a way to screw them. He has the rights to the Kitten Mittens and gave Dennis Maureen’s debt. Every line is delivered perfectly by Brian Unger.
Mary Lynn Rajskub has only made a couple of appearances as Dennis and Dee’s cousin Gail the Snail, but she’s always been hilarious. Whether she’s inviting the Gang to a rave or getting lashed with table salt or following Mac around and calling him her boyfriend, Gail is, without a doubt, the funniest supporting character on the show.
It’s not at all surprising since Rajskub is one of the sharpest voices in comedy right now. Her most recent appearance was in the all-female reboot of the Wade Boggs episode, in which the show’s female characters attempted to beat the Boggs drinking record.