The 5 Best It’s Always Sunny In Philadelphia Side Characters, Ranked

“The gang” on “It’s Always Sunny in Philadelphia” are five of the most extreme, ridiculous, poorly behaved people in television history. While the show is so much more than just a show about terrible people, it is admittedly populated by some pretty awful human beings. Charlie (Charlie Day), Mac (Rob McElhenney), Dennis (Glenn Howerton), Sweet Dee (Kaitlin Olson), and Frank (Danny DeVito) are pretty entertaining all on their own, but they also have to interact with other people, which means expanding the “Always Sunny” world with more weird and wild characters. There are dozens of recurring characters that appear throughout the show’s 16 seasons, but some of them have made their mark more than others, either as willing accomplices in the gang’s schemes or as their unfortunate targets.

There aren’t really many decent people who engage with the gang for long without being broken or simply bailing on the situation, so most of the characters who have really stuck around are just as deranged as the gang in their own, unique ways. Whether they’re as bizarre 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 of the characters in the gang’s orbit: They’ve all been permanently changed by the gang in some way. Of these inhabitants of the show’s fictional Philadelphia, some have almost managed to hold their own against the gang over the years and have made an impact on the series, bringing the laughs. So who’s the best of the worst Philly has to offer? Let’s take a look at the five best “It’s Always Sunny in Philadelphia” side characters.

There aren’t very many people who can out-chaos the gang, but Bill Ponderosa (Lance Barber) might be the chaos champion. Introduced as Dee’s former high school crush, Bill is a flaming dumpster fire of a man who cheats on his wife with multiple mistresses (including Sweet Dee) before an ugly divorce leaves him broke and alone. He ends up addicted to all kinds of drugs and asks Frank to be his Narcotics Anonymous sponsor, which only leads to more depravity because Frank is the world’s worst sponsor. Seriously, Frank pretty much encourages Bill to do drugs and even get drugs for him. (For an added layer of awfulness, Bill’s dealer is his teenage son, who calls his father by a name that I cannot even begin to print here.) Bill was also Dennis’s brother-in-law for a short time when Dennis was briefly married to Bill’s sister Maureen (Catherine Reitman).

Pondy is pretty much always guaranteed to be a great shot of gallows humor mixed with pure unfiltered mayhem, and he’s probably one of the worst human beings the gang regularly engages with. The only one who comes close is Charlie’s pedophile Uncle Jack (Andrew Friedman), who is pretty funny himself but can also make things really, really uncomfortable. Besides, Uncle Jack would never do something as irresponsible as put bath salts in the milk at his sister’s wedding, so Pondy’s penchant for poor choices that impact everyone gives him the edge here.

Another character sure to bring a chaotic element to the mix is Artemis Dubois (Artemis Pebdani), who first appeared all the way back in the season 1 episode “Charlie Has Cancer” as a young woman in Dee’s acting class who lost her job at the Wawa (convenience store), so Dee brings her on at Paddy’s to be a “‘Coyote Ugly’-style bartender.” She’s one of Dee’s only friends, though they have a rather adversarial relationship at times because Artemis plays by her own rules and refuses to let Dee bully her in any way. She’s also very loudly her own woman, announcing to a club full of people that she had an intimate body part bleached as a kind of bizarre mating call. 

While she didn’t catch any hotties on her “Sex and the City” night with Dee, Artemis does regularly hook up with Frank. The two have an on-and-off-again relationship that never seems too committed, though Artemis introduces Frank to her family while they sit shiva in the season 11 episode “Being Frank,” so it’s at least somewhat serious. Artemis is a free spirit who can always be counted upon to provide some witty commentary on a situation and maybe a bit of her special brand of judgment. She’s also never above being involved in some of the gang’s grosser moments, like her incredible investigation and speech about feces in “Who Pooped the Bed?” or giving a whole plane full of women ayahuasca and enjoying the ensuing vomit fountains. Somehow Artemis has managed to stay her fabulous self despite her many interactions with the gang, who tend to cause pretty intense changes in others, but that’s fine because she’s always hilarious. 

Dennis and Dee’s adoptive father and Charlie’s potential biological father Frank (it’s a long story) has become a part of the gang with time, but he’s not the only parent to bring hilarity on “It’s Always Sunny.” Charlie’s mom, Bonnie Kelly (Lynne Marie Stewart), and Mac’s mom, Mrs. McDonald (Sandy Martin), are both hilarious in their own right but are even better together. The duo were first paired 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 one another. They collaborated to con everyone into giving them money after accidentally mowing down a Virgin Mary statue with their car in “Charlie’s Mom Has Cancer” and were even the subjects of a fake sitcom created by Dennis called “Old Lady House.” 

Mrs. Mac is a chain-smoking former Jiffy Lube employee who rarely utters a word, while Bonnie is a high-strung alcoholic sex worker with obsessive-compulsive disorder. They are polar opposites in many ways, but they bonded over their more conservative beliefs, which their sons accept as sort of a racist, less ideal “Golden Girls” situation. The relationship between Charlie and Mac is actually kind of sweet, but the one between their mothers is mostly just entertaining. When you add in Uncle Jack or Luther McDonald (Gregory Scott Cummins), Mac’s violent ex-felon father, things are bound to get funny.

Like the Ponderosas, the McPoyle family have all seemed to have some kind of encounter with the gang. The McPoyles are a sprawling family of inbred oddities under patriarch Pappy McPoyle (played by director Guillermo del Toro), though brothers Liam (Jimmi Simpson) and Ryan (Nate Mooney) definitely clash with the gang the most often. Fans were first introduced to the pair in the season 1 episode “Charlie Gets Molested” as they falsely accused a former teacher of molesting them and Charlie ratted them out, leading to a feud that’s lasted for 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 members of the gang try to figure out who got Dee pregnant and cheered on Mac’s bathroom hookup with Margaret. Unfortunately, in season 8 Liam lost an eye due to the drugged milk at his wedding (courtesy of Bill Ponderosa, encouraged by Frank), so the original grudge began anew. 

The McPoyles are absolutely hilarious even in small bursts, in large part because of the performances by Simpson and Mooney. Both of them know how to really lean into the weirdness of their characters and deliver their lines with unusual inflections that make them even funnier. Liam screaming “you will call her!” at Mac after that hookup with Margaret is one of the funniest lines in the whole series, and it’s all because of Simpson’s demented delivery. Thankfully, the McPoyles are still around and beefing with the gang as of season 16, so hopefully we’ll get to laugh at their antics for as long as the series is on the air.

There’s only one “It’s Always Sunny in Philadelphia” side character who has gotten an episode all to himself, and that’s Matthew “Rickety Cricket” Mara. He’s the most important side character in the series because he’s not only wildly funny as played by David Hornsby, who also writes for the show, but he is also the most reflective of the gang over time. While other characters have absolutely changed, like Ponderosa’s descent into drug-fueled mania or Liam’s lost eye, no one has taken on the brunt of the gang’s abuse quite like Cricket. Called “Rickety Cricket” in high school because of his leg braces, he had a massive crush on Dee that she used to torture him. He ended up becoming a Catholic priest, only to leave the church because Dee confessed her love to him. (She almost immediately changed her mind, of course.) After leaving the priesthood, Cricket went on a downward spiral, becoming an unhoused drug addict who will debase himself for money. After being locked in Dennis and Mac’s apartment during a failed Thanksgiving party, he’s also burned on most of his body like a goateed Freddy Krueger, growing more grotesque on his outside as his moral integrity also decays. 

By season 16, Cricket is pimping out young men and is well on his way to being a low-level crime lord, so there’s no telling how low he can go. If there’s any true proof of the gang’s depravity, it’s that they took a wholesome, kind-hearted priest and turned him into a powder-snorting, gigolo-slapping demon of a man. Somehow, through the magic of good writing and Hornsby’s hilariously earnest performance, Cricks manages to be funny instead of sad — at least most of the time. He’s the gang’s mirror, their inverted moral compass, and he’s the best side character in all of “It’s Always Sunny.”