For more than fifteen seasons, *It’s Always Sunny in Philadelphia* has centered around the outrageous behavior of “The Gang”—a group of deeply flawed characters who consistently lack any sense of morality or consequence. While Mac, Dennis, Dee, Charlie, and Frank are at the heart of Paddy’s Pub, the show truly shines thanks to its memorable supporting characters. These often-unlucky individuals usually fall victim to the Gang’s schemes, leading to comical and often heartbreaking results.
Whether they’ve been rivals, temporary friends, or constantly caught in the crossfire, these ten characters have become integral to the hilarious mayhem of ‘It’s Always Sunny in Philadelphia,’ solidifying their place in the show’s history and proving that at Paddy’s Pub, everyone thrives on shared misfortune.
10) The Lawyer
The lawyer only shows up when the Gang is in serious trouble – which is pretty common – or when he chooses to help people they’ve harmed. He usually responds to their ridiculous plans with obvious frustration, and somehow ends up caught in the middle of the chaos.
He’s the only serious person amidst a chaotic scene, a dedicated professional visibly burdened by having to defend truly difficult clients. Recently, he suffered severe injuries – losing an eye and being badly burned with hot oil used for frying food – during a bizarre incident involving Charlie and a moving ambulance.
9) Bill Ponderosa
Dee has a complicated history with Bill, a man she used to have a teenage crush on. Their relationship has been on-and-off, and Bill has always been troubled – he’s unfaithful to his wife, struggles with drug use (often with his friend Frank), and seems to lack remorse. Though Dee remembers Bill being very attractive when she was younger, she realizes he’s changed a lot, yet she continues to have an affair with him.
Honestly, watching Bill’s journey on the show is just… wild. It’s both incredibly dark and hilariously sad to see how much he’s changed. There’s this one episode where he basically admits he’s trying to drink himself to death at Paddy’s, and the Gang doesn’t even blink! Now he’s like a warning sign of what can happen to someone who gets sucked into their world, and he’s totally willing to go along with even the most awful things they do – he’s practically sunk to the same level as Charlie, Mac, Dennis, Dee, and Frank!
8) Maureen Ponderosa
Dennis decided it was time to get married, so he tracked down his old high school girlfriend, Maureen Ponderosa. They got married immediately, and Maureen moved into the apartment Dennis shared with Mac, kicking Mac out in the process. It wasn’t long after the hasty wedding that Dennis realized Maureen was incredibly strange, and he became fixated on her noticeable gap-toothed smile. A running joke throughout the series is Maureen’s gradual and peculiar transformation into a cat, starting with extensive plastic surgery and culminating in her fully identifying as feline. This ultimately leads to her darkly comedic and supposedly accidental death after she falls from a rooftop – though everyone suspects Dennis intentionally pushed her.
She repeatedly tried to upset Dennis, either by asking for money or by deliberately behaving in ways she knew would embarrass him. This consistently triggered his need to control situations and revealed a disturbing side of his personality. Even after she died, she wanted to provoke him one last time by requesting he bury her ashes in a pet cemetery – something she knew he’d strongly object to.
7) Gail the Snail
Okay, so there’s this character, Gail – everyone calls her Gail the Snail – and she’s Dee and Dennis’s cousin. Honestly, she’s *designed* to be awful. The writers clearly want you to hate her! She keeps popping up, and it’s always the same deal: she’s totally clueless, tries way too hard to seem cool and grown-up, and has zero self-awareness. It’s painful to watch, but in a weirdly funny way, I guess. She’s just… a lot.
She’s a perfect contrast to the group, who clearly dislike her, even though they’re just as bad. They try to get rid of her by throwing salt at her – a cruel tactic they call “salting the snail” – until she leaves. Her presence is funny because it forces them to face someone they actually see as even more awful and pathetic than themselves, which isn’t easy to achieve comedically.
6) The Waitress
Charlie is completely fixated on the Waitress, relentlessly following her, which he believes he’s doing to help. Unfortunately, she’s constantly having bad luck, often losing jobs because of the Gang’s meddling. Dee sees the Waitress as her greatest rival and repeatedly sabotages her recovery from addiction, pushing her back into substance abuse.
The character experiences constant hardship, though it’s often presented with a dark humor. She’s a victim of the other characters’ thoughtlessness, as they repeatedly sabotage her relationships, work, and well-being. They don’t even realize the damage they’re causing, and any positive moments she has are quickly destroyed by Charlie’s actions.
5) Artemis Dubois
Artemis is Dee’s friend – a bit more grounded than most, but still wonderfully eccentric. She’s full of energy and known for her over-the-top personality, free-spirited attitude, and surprisingly inventive use of fast-food ingredients. What makes Artemis unique among the regulars is that she doesn’t get caught up in the Gang’s usual bad behavior. She often provides a surprisingly sensible perspective – though ‘sensible’ is relative when you’re around the crew at Paddy’s Pub – and she’s incredibly self-assured.
Artemis instantly makes any situation more interesting, usually by causing some kind of playful chaos – like inventing a persona during a bowling game or pulling elaborate pranks. She’s delightfully unpredictable and a great foil for Frank, sometimes helping The Gang and other times working against them. Her dedication to performance, combined with her unusual jobs, brings a unique and dramatic energy to the show.
4) Liam & Ryan McPoyle
Liam and Ryan McPoyle are truly unsettling brothers and the heads of the strange McPoyle family. The McPoyles are infamous for their disturbing relationships, obsession with milk, and long-held grudges against the main group. Liam takes the lead as the more threatening of the two, while Ryan silently and creepily supports him.
The McPoyles are a comically irritating family who are always looking for a reason to be upset. They’re constantly claiming someone has wronged them – whether it’s something minor like tampering with wedding milk or something serious like shooting a relative – and their disputes always escalate into dramatic events like kidnappings, hostage situations, or courtroom battles. Despite being rivals, they’re strangely amusing.
3) Mrs. Mac
Let me tell you, Mrs. Mac is a character. She barely speaks – mostly just grunts, sighs, and a whole lot of coughing, likely from the constant chain-smoking. But honestly, her silence is hilarious! It screams disappointment in her son, Mac, and his buddies, and it’s way funnier than any lines she *could* say. The irony is, Mac is always going on about how much his mom adores him, making her silent treatment even more brilliant.
You know, unlike Frank or Mrs. Kelly who were actively awful, Mrs. Mac was just…distant. She didn’t really *do* much, but her coldness really hurt Mac, and honestly, it felt like looking in a mirror – she seemed stuck, just like him, and couldn’t really connect with anyone emotionally. But some of the funniest parts of the show, for me, were when Mrs. Mac and Bonnie Kelly ended up having to live together – those two were a hilarious disaster!
2) Cricket
Rickety Cricket, born Matthew Mara, is arguably the most heartbreaking example of someone whose life was ruined by interacting with Dee and the Gang. Dee discovered Cricket had a long-standing crush on her and cruelly used this to manipulate him. He left the priesthood believing she reciprocated his feelings, but she rejected him, and her and the Gang’s actions led him down a path of homelessness, addiction, physical injury, and despair.
He’s so desperate for acceptance that he’ll do anything the gang asks, even humiliating things like eating lemons or hosting a strip show at the pub. They exploit him purely for their own amusement, showing they have no compassion. This constant string of bad luck, which gets increasingly worse each time we see him, is a key part of the show’s darkly funny and pessimistic outlook.
1. Rum Ham
Frank brought a ham that he’d soaked in rum with him on a trip to the Jersey Shore. He did this so he and Mac could have alcohol on the beach. The two of them quickly became oddly attached to the rum-soaked ham, treating it almost like a person.
When Rum Ham is accidentally thrown overboard, Frank reacts with genuine distress, yelling apologies. Fortunately, a group of partygoers on a boat happen to rescue Frank and Mac, and also pull Rum Ham from the water, much to their relief. This whole situation perfectly showcases the wildly funny and unexpected humor that makes *It’s Always Sunny in Philadelphia* so unforgettable.
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2025-10-08 17:14