10 Best ‘It’s Always Sunny in Philadelphia’ Characters, Ranked

The black comedy It’s Always Sunny in Philadelphia has been entertaining audiences with the exploits of a narcissistic and depraved group of friends, the Gang, in Philadelphia dive bar Paddy’s Pub for 16 seasons. Its plots range from the characters’ various scams to tackling larger social and political issues, all in its own hilarious yet dark way. The show debuted in 2005 and first aired on FX, where it was a fixture before it moved to the network’s second channel, FXX, in 2013 for Season 9. It is the longest-running live-action comedy in television history, with at least two more seasons to come.

The Gang makes It’s Always Sunny in Philadelphia as hilarious and dark as it is, thanks to their scheming and general disregard for other people, including each other. But other characters are just as crucial to the show, from the Gang’s friends and family to people whose lives they’ve ruined with their selfishness and cruelty. Though none are particularly good or likable, they do make for fantastic entertainment.

10 Uncle Jack

Portayed by Andrew Friedman

Charlie’s Uncle Jack Kelly started off as a side character, but over the years, he’s had a greater presence on the show. When Charlie was a kid, Jack lived with him and his mother, and it’s often implied that Jack molested Charlie at the time and that the events are what inspired Charlie to write “The Nightman Cometh.” Jack works as a lawyer and sometimes represents the Gang, leading him to interact with the Lawyer.

Uncle Jack has been creepy and unsettling from his first moments onscreen, and he’s only gotten worse as the series has progressed, and he’s been featured more, as he’s eager to touch and hug almost anyone he interacts with. He is often shown to be insecure about the size of his hands, which, in his opinion, are too small, and obsessed with the size of others’ hands, especially the Lawyer’s hand, leading him to wear large fake hands which he insists are real.

9 The Lawyer

Potrayed by Brian Unger

Similar to the Waitress, the subject of Charlie’s affection, the Lawyer is a character without a name often getting pulled into the Gang’s antics. He’s a Harvard-educated lawyer who was first introduced when he read Barbara’s will to Dee, Dennis and Frank and made additional appearances throughout the series, typically when a member of the Gang had a new idea for a money-making invention, and they never paid him for his work.

The Lawyer can be charming and likable, in contrast to the Gang, who he strongly dislikes, and it’s obvious why. He’s a “straight man” in the midst of their chaos, and his clear exasperation at dealing with them — and his clear intelligence and competence — makes for some great moments. Because he knows they won’t actually read any contracts they sign, he’s able to secure himself 100% of the profits from any Paddy’s merchandise, as well as ownership of their invention, kitten mittens. It would be despicable if the Gang didn’t deserve it.

8 Artemis Dubois

Portrayed by Artemis Pebdani

Artemis is a friend of Dee’s from an acting class. After meeting Frank, the two struck up a romance. She often helps the Gang in whatever capacity she’s needed, whether that’s solving an episode’s mystery or assisting in a scheme, and she gets results. She’s also tried just about every drug imaginable, leading her to announce she doesn’t remember most evenings. Most importantly, she was the director of Charlie’s musical, “The Nightman Cometh.”

Although it’s hard to imagine Dee having other friends — or really, any friends at all — it is easy to understand why Artemis is one of them. She’s just as crass as Dee, if not more so, with a bold personality and a sense of confidence which make her a great fit for the Gang, and seems to say what’s on her mind, no matter what. Things are guaranteed to get messier whenever she’s involved, which also means they’ll get even funnier.

7 The Waitress

Portrayed by Mary Elizabeth Ellis

The nameless Waitress is the side character who has the distinct attribute of showing up the most in the series without ever being a main character. She first appeared in the very first episode and has been on the show regularly ever since. She went to high school with the Gang and used to work at a coffee shop Charlie often went to. Charlie is in love with her and proposed to her using “The Nightman Cometh,” but naturally, she was unimpressed by the musical and turned him down.

Although the Waitress is typically around as the subject of Charlie’s desire and is annoyed with him, she’s had some hilarious moments in her own right; and despite being justifiably horrified by the Gang’s antics (she sometimes calls out their behavior), she’s not perfect and has had her share of depraved behavior. Still, it’s easy to feel sorry for her, since she seems unable to escape from the Gang and their scheming, sometimes at her expense.

6 Matthew “Rickety Cricket” Mara

Portrayed by David Hornsby

Cricket went to high school with the Gang and entered the priesthood. After expressing his love for Dee, she turns him down and manipulates him into leaving the priesthood, kicking off a downward spiral which continued over the course of the series. Cricket became homeless and developed a drug problem, and his horrible experiences even impacted his physical appearance, as he accumulates more and more scars over the course of the series.

Cricket is something of a cautionary tale, showing what can happen to a person at the hands of the Gang. Hornsby is hilarious in the role, whether he’s afraid of what the Gang will get him into next or acting irrational at the height of his addiction, especially because he always seems to be upbeat and in good spirits, no matter how horrible his situation is. It’s hard to imagine things getting any worse for Cricket, but they probably can.

5 Dennis Reynolds

Portrayed by Glenn Howerton

Dennis is one of the co-owners of Paddy’s Pub and the twin brother of Dee. It’s often implied Dennis may be a serial killer. He has a very close friendship with Mac, to the point that Dee once aptly compared them to an old married couple. He was married to his high-school sweetheart, Maureen Ponderosa, for a brief period of time. At the end of Season 12, he leaves the bar to return to his secret family, only to return almost immediately in Season 13.

Dennis can be charismatic, but at heart, he’s arrogant and manipulative, especially when it comes to woman; and he has a tendency to try to manipulate women into sleeping with him. He’s possibly the worst member of the Gang, which is saying something, and is also sort of the “straight man,” especially compared to the others. He’s also prone to angry outbursts when he doesn’t get his way. But his horrible behavior also leads to some of the show’s funniest moments.

4 Deandra “Dee” Reynolds

Portrayed by Kaitlin Olson

Dee, nicknamed Sweet Dee, is Dennis’ twin sister and she works as a bartender at Paddy’s. One of the show’s running gags compares Dee to a bird, just one example of how she’s often bullied by the guys in the Gang. Dee once aspired to be an actress, but her stage fright and lack of skills were probably a factor in why that career path didn’t pan out.

Dee is just as sadistic as the guys, if not more so, thanks to her selfish and manipulative tendencies and her crass personality, despite being made fun of as the girl in the group, she’s managed to pull off some things that even horrified the guys. She’s at her funniest when she’s being combative and aggressive, and she also has some of the show’s funniest lines. But some of her best moments are also thanks to Olson’s dedication to physical comedy.

3 Ronald “Mac” McDonald

Portrayed by Rob McElhenney

Mac is own of the bar’s co-owners and also serves as its bouncer. His father, Luther, has been in prison for most of Mac’s life, and his mother (Sandy Martin) is indifferent towards him. Mac and Dennis are close friends and live together. Mac is gay and officially came out in Season 12, although the Gang thought he was lying at first, then later came out to his father through an interpretive dance in the Season 13 finale, one of the most powerful, emotional episodes of the series.

Mac is just about as dumb as Charlie, if not more so. He’s typically not deliberately cruel, especially compared to the rest of the Gang. He is a Catholic, which contributed to his struggle to accept his homosexuality. Mac is also one of the most reasonable characters and one of the few that’s actually experienced some growth over the course of It’s Always Sunny in Philadelphia; but to be clear, that doesn’t mean he’s redeemed himself. He’s still, very much, a horrible person.

2 Charlie Kelly

Portrayed by Charlie Day

Charlie is the janitor of Paddy’s Pub and was once one of its co-owners. He had a difficult childhood, with an absent father and inattentive mother. As an adult, he lives with Frank. He wrote the infamous musical “The Nightman Cometh” in an elaborate plan to propose to the Waitress, who he is in love with and who is completely uninterested in him, for good reason. He’s responsible for some of the Gang’s more ridiculous and bizarre schemes.

Charlie is possibly the most chaotic and unhinged member of the Gang, and one of the most hilarious as a result. He is often shown to be not very intelligent and is illiterate, although he does have a creative side to him. He is generally nicer than the rest of the Gang and is the most likable of the group, even relatable at times, but he is still prone to outbursts.

1 Frank Reynolds

Portrayed by Danny DeVito

Frank joined the cast of It’s Always Sunny in Season 2 as the father of Dennis and Dee, although it was later revealed he wasn’t their biological father and was possibly Charlie’s father. He is divorced from their mother, Barbara. As a child, he was put in a mental institution, then later released. As a result, he no longer trusts therapists. He was once a successful businessman and is now part owner of Paddy’s. He lives with Charlie in a tiny apartment, where they sleep together on a pull-out couch.

Frank quickly became one of the most memorable characters on It’s Always Sunny in Philadelphia after he was introduced in Season 2. Needless to say, he was a terrible father to Dennis and Dee when they were kids and remains so now that they’re adults. Although it doesn’t show up often, Frank does have a vulnerable, sensitive side to him. Best of all, though, there’s seemingly no physical gag DeVito will say no to as Frank, making for some of the show’s funniest moments.

Watch On Hulu

NEXT: Every Recurring Character in ‘It’s Always Sunny in Philadelphia,’ Ranked by Unhinged-ness