Top 5 'It's Always Sunny in Philadelphia' Side Characters, Ranked

The “Gang” from “It's Always Sunny in Philadelphia” are five of the most extreme, absurd and inappropriate people in the history of television. While the show is much more than just a show about terrible people, it must be admitted that it is inhabited by some terrible people. Charlie (Charlie Day), Mac (Rob McElhenney), Dennis (Glenn Howerton), Sweet Dee (Kaitlin Olson) and Frank (Danny DeVito) are pretty fun on their own, but they also have to interact with other people, which means expanding the world” Always Sunny” with more strange and wild characters. There are dozens of recurring characters throughout the show's 16 seasons, but some have made their mark more than others, either as willing accomplices in the gang's plans or as ill-fated targets.

There aren't many decent people who stay involved with the gang for long without getting cracked or just saving the day, so most of the characters that are really left here are just as demented as the gang in their own unique ways. Whether they're as weird as the inbred, milk-drinking McPoyles, or they're just the unlucky object of Charlie's obsession, like the poor unnamed waitress, one thing unites all the characters in the gang's orbit: they've all been permanently changed in some way by the gang. Some of the residents of the show's fictional Philadelphia have almost managed to take on the gang over the years and have made an impact on the show with laughs. So who are the best of the worst Philly has to offer? Let's take a look at five of the best side characters in “It's Always Sunny in Philadelphia.”.

There aren't many people who can bring chaos to a gang, but Bill Ponderosa (Lance Barber) may be a master of chaos. Introduced as Dee's old high school crush, Bill is a burning dumpster of a man who cheats on his wife with multiple lovers (including Sweet Dee) before a nasty divorce leaves him broke and alone. He ends up becoming addicted to all kinds of drugs and asks Frank to become his Narcotics Anonymous sponsor, which only leads to more depravity because Frank is the worst sponsor in the world. Seriously, Frank basically encourages Bill to do drugs and even get drugs for him. (For added creepiness, Bill's dealer is his teenage son, who calls his father a name I can't even begin to print here.) Bill was also Dennis' brother-in-law for a short time, when Dennis was briefly married to Bill's sister Maureen (Catherine Reitman).

Pondy is almost always guaranteed to be a great dose of gallows humor mixed with pure, unfiltered chaos, and is probably one of the worst people the gang comes into contact with on a regular basis. The only one who comes close is Uncle Jack, Charlie's pedophile (Andrew Friedman), who is quite funny himself, but can also really change everything, Really uncomfortable. Plus, Uncle Jack would never do something as irresponsible as adding bath salts to milk at his sister's wedding, so Pondy's tendency to make bad choices that affect everyone gives him an advantage here.

Another character sure to add an element of chaos to the mix is ​​Artemis Dubois (Artemis Pebdani), who first appeared back in the season one episode “Charlie Has Cancer” as a young woman from Dee's acting class who has lost her job at Wawa ( convenience store), so Dee invites her to Paddy's to be a “Coyote Ugly” style bartender. She is one of Dee's only friends, although they have a rather hostile relationship at times as Artemis plays by her own rules and does not allow Dee to abuse her in any way. She is also a very vocal woman of her own, announcing to a club full of people that she has bleached her private part as part of a bizarre mating call.

Although she didn't catch any hotties during her Sex and the City night with Dee, Artemis has been hanging out with Frank on a regular basis. The two have periods of a relationship that never feels very committed, although Artemis introduces Frank to her family when they sit with Shiva in the season 11 episode “Being Frank,” so it's at least a little serious. Artemis is a free spirit who can always be counted on for a witty commentary on a situation and maybe a little of her special way of judging. She also never hesitates to engage in some of the gang's more disgusting moments, such as her amazing investigation and speech about feces in “Who Pooped the Bed?” or giving an entire plane full of female ayahuasca and enjoying the resulting fountains of vomit. Somehow Artemis has managed to maintain her fantastic personality despite her many interactions with the gang, which tends to cause some pretty intense changes in others, but that's okay because she's always hilarious.

Dennis and Dee's adoptive father and Charlie's potential biological father, Frank (it's a long story), became part of the gang over time, but he's not the only parent who brought hilarity to “It's Always Sunny.” Charlie's mom Bonnie Kelly (Lynne Marie Stewart) and Mac's mom Mrs. McDonald (Sandy Martin) are hilarious on their own, but they're even better together. The duo first teamed up in the Season 6 episode “Mac's Mom Burns Her House Down” after Mrs. Mac moved in with Bonnie and the two women realized they could get along and help each other. They worked together to trick everyone into giving them money after accidentally destroying a statue of the Virgin Mary with a car in the movie “Charlie's Mom Has Cancer”. They were even featured in a spoof sitcom created by Dennis called “Old Lady's Home.”

Mrs. Mac is a chain-smoking former Jiffy Lube employee who rarely utters a word, while Bonnie is a nervous alcoholic who suffers from obsessive-compulsive disorder. In many ways they are completely different from each other, but they are united by their more conservative beliefs, which their sons accept as a racist, less ideal “Golden Girls” situation. The relationship between Charlie and Mac is actually quite sweet, but the one between their mothers is just hilarious. Throw in Uncle Jack or Luther McDonald (Gregory Scott Cummins), Mac's brutal ex-con father, and things are sure to get funny.

Like the Ponderosa, the McPoyle family appears to have had some contact with the gang. The McPoyle's are a sprawling family of inbred oddities led by patriarch Pappy McPoyle (played by director Guillermo del Toro), although brothers Liam (Jimmi Simpson) and Ryan (Nate Mooney) are much more at odds with the gang. Fans first met the pair in the season 1 episode “Charlie Gets Molested,” when they falsely accused a former teacher of molestation and Charlie criticized them, leading to a feud that has lasted 16 seasons and counting. In Season 3, they teamed up with their mute sister Margaret (Thesy Surface) to hold the gang hostage, then in Season 6, they helped the male gang members try to find out who got Dee pregnant and cheered Mac on in the bathroom with Margaret. Unfortunately, in Season 8, Liam lost an eye due to drugged milk at his wedding (courtesy of Bill Ponderosa, at Frank's urging), so the original resentment started all over again.

The McPoyles are absolutely hilarious, even in small burststhanks in large part to the performances of Simpson and Mooney. They both know how to really capture the strangeness of their characters and add unusual touches to their lines that make them even funnier. Liam shouts “you call her!” on Mac after that encounter with Margaret is one of the funniest lines in the entire series, and it's all because of Simpson's insane delivery. Luckily, the McPoyles are still around and have been working with the gang since season 16, so hopefully we'll be laughing at their antics for as long as the show airs.

There's only one side character in It's Always Sunny in Philadelphia who has an episode to himself, and that's Matthew “Rickety Cricket” Mara. He is the most important side character in the series because he is not only wildly funny as played by David Hornsby, who also writes the series, but over time also the most thoughtful of the entire crew. While other characters have completely changed, like Ponderosa's descent into drug mania or Liam's lost eye, no one took the brunt of gang violence like Cricket. Nicknamed “Rickety Cricket” in high school due to his leg braces, he had a huge crush on Dee, which she used to torture him. He eventually became a Catholic priest, but left the church because Dee confessed her love for him. (She changed her mind almost immediately, of course.) After leaving the priesthood, Cricket fell into a downward spiral, becoming a homeless drug addict who degraded himself for money. After being locked in Dennis and Mac's apartment during a Thanksgiving party gone wrong, he too is there, burning throughout most of his body like Freddy Krueger with a goatee, becoming increasingly grotesque on the outside as his moral integrity fades.

In season 16, Cricket has been taking care of young men and is on his way to becoming a low-level criminal, so there's no telling how low he can go. If there's any real evidence of the gang's depravity, it's that they took a healthy, kind-hearted priest and turned him into a drug-snorting, gigolo-beating male demon. Somehow, thanks to the magic of good writing and Hornsby's hilariously earnest performance, Cricks manages to be funny rather than sad – at least most of the time. He is the gang's mirror, their inverted moral compass, and the best side character in all of It's Always Sunny.