FXX’s It’s Always Sunny in Philadelphia is back with its seventeenth season and that means it’s finally time for fans to reunite with Charlie Kelly (Charlie Day), Dennis Reynolds (Glenn Howerton), Ronald “Mac” McDonald (Rob Mac), “Sweet Dee” Reynolds (Kaitlin Olson), and Frank Reynolds (Danny DeVito). But what about the supporting characters of It’s Always Sunny? Well time will tell in that regard, but It’s Always Sunny isn’t It’s Always Sunny with just the Gang alone. The Gang needs irritated and offended folks to bounce off of. What follows are the best of the best of those It’s Always Sunny characters in the Gang’s orbit.
That means anyone outside the five members of the Gang. Anyone was subject to inclusion, provided they’ve been featured in four or more episodes. Just missing the cut were Ben the Soldier, Rex, Artemis, Luther McDonald, and Carmen, but they’re all wonderful (and in Rex’s case, The Master).
10) Gail the Snail (Mary Lynn Rajskub)
A lifelong nuisance to Dee and Dennis Reynolds, Gail “The Snail” is so disgusting that she even sicks Charlie out. And he walks around in sewers.
Gail debuted in one of Sunny‘s very best episodes: Season 5’s “The Gang Gives Frank an Intervention.” We’re introduced to her neediness and lack of desire to ever swallow her spit. She then returned in Season 9’s “The Gang Squashes Their Beefs,” where she and Dee did not end up squashing their beef, then in Season 13’s “The Gang Beats Boggs: Ladies Reboot,” where she forces her way into Dee’s redundant contest, and most recently in Season 16’s fantastic “The Gang Goes Bowling.”
9) Bonnie Kelly & Mrs. Mac (Lynne Marie Stewart & Sandy Martin)
Many of the best Charlie Kelly episodes of Sunny also involve his mother, Bonnie. They have a compelling dynamic: he’s her entire world while she’s usually an annoyance to him. But, even when she’s asking him to vacuum the ceiling, he does do it out of love.
Then there’s Mrs. Mac, who Mac loves with all his heart even though she barely even knows he’s a person who exists. We’re making this one a twofer because, while very different, these women are integral to understanding who two members of the Gang are, and why they are the way they are.
8) Uncle Jack (Andrew Friedman)
Only It’s Always Sunny in Philadelphia could turn a child abuser like Uncle Jack into a source of humor. Perhaps it’s because of Charlie’s denial of an incident ever happening mixed with Uncle Jack’s flagrant display of being exactly as he’s just been described.
It really comes down to how Andrew Friedman plays the character. He’s goofy and creepy, but not an overly hateable predator type. But he absolutely touched Charlie, even if Charlie will never admit it. That’s as clear as his weird issue with the size of his hands.
7) Z (Chad L. Coleman)
Chad L. Coleman has been a standout on shows like The Wire and The Walking Dead, and his work as Z on Always Sunny ranks right up there with his work on those A-list properties. Coleman has only been on five episodes of Sunny, but he’s stolen every last one.
First off there was a cameo in Season 6’s “Charlie Kelly: King of the Rats,” where we meet him and the rest of the crew Charlie and Frank have been hanging out with under a bridge. Then, in that same season, he had a hilarious, brief conversation with Ben the Soldier about jean shorts in “Dee Gives Birth.” Z then popped up again in Season 9’s “The Gang Tries Desperately to Win an Award,” Season 12’s “The Gang Turns Black,” and Season 14’s “A Woman’s Right to Chop,” where he’s temporarily enlisted to perform a dog abortion.
6) The Lawyer (Brian Unger)
Brian Unger’s the Lawyer debuted in Season 3’s “Dennis and Dee’s Mom Is Dead,” where he informed Dennis, Dee, and Frank of Barbara Reynolds’ will (including a burn about Frank’s “Fat monkey heart”). It takes all of one scene for him to become exhausted by their volatility.
The Lawyer came back twice in Season 5, first in “The Gang Exploits the Mortgage Crisis,” where he protects a foreclosed-upon family from the Gang, and then in “Paddy’s Pub: Home of the Original Kitten Mittens,” where Dennis offers to throw a “frame bang” his way so his wife can’t “clear him out.” He came back the next season for “Dennis Gets Divorced,” where he offered his services pro bono to Maureen Ponderosa just to irritate Dennis (and get some palpable delight out of it) and returned in Season 8’s “Pop-Pop: The Final Solution,” where he was anxious to pull the plug on Dennis and Dee’s Nazi grandfather. His most recent appearance was his showiest in “McPoyle vs. Ponderosa: The Trial of the Century,” where he ended up getting his eye pecked out by a bird.
5) Maureen Ponderosa (Catherine Reitman)
Maureen and Bill Ponderosa were introduced in the two-parter opening of Season 6. It’s immediately established that Bill is a dirtbag while Maureen is, well, super into cats. As their arcs progressed, Bill has only gotten worse (his own family couldn’t care less if he lives or dies), while Maureen has gone through some drastic, far more interesting, changes.
Maureen came back in Season 7 for another two-parter, this time the season’s finale, “The High School Reunion.” In it, it’s revealed that she’s gotten a diamond stud in her dead tooth…which still makes it a dead tooth. In Season 8’s “The Maureen Ponderosa Wedding Massacre,” she gets fake breasts, which wins Dennis back (always her ultimate goal) for all of about five minutes. Then, in Season 10’s “Mac Kills His Dad,” she has begun her transformation into a cat, while Season 11’s “McPoyle vs. Ponderosa: The Trial of the Century” has her pretty much all the way there. After all, she chases a laser around the courtroom. In the following season’s “Making Dennis Reynolds a Murderer,” it’s revealed that she died after trying to leap between buildings…or was she pushed?
4) The Waiter (Michael Naughton)
The first time Michael Naughton appeared on Sunny, he was intended to be a one-off guest star. Specifically, he was the hiring manager who gave Charlie and Mac their mailroom gig in Season 4’s “Sweet Dee Has a Heart Attack.” But his line deliveries were so amazing Rob Mac and Charlie Day just couldn’t keep it together. The Season 4 blooper real is worth watching just for that scene alone.
So, they brought him back, this time as a new character: the Waiter at Guigino’s (though the HR Director could have become a waiter, that was never confirmed nor disputed on The Always Sunny Podcast). Like all other normal people in the Gang’s orbit, he is forever at the brunt of their dismissiveness, but he never hesitates to throw it back at them in his own way. He did so in Season 8’s “The Gang Dines Out” by embarrassing Dee, for instance. He then came back in Season 10’s “The Gang Group Dates” and “The Gang Spies Like U.S.,” where the running joke about them never remembering him kicked off. He then popped up two more times in Season 13 and, most recently, in Season 14’s “The Gang Chokes,” where Frank hilariously forces himself into the Waiter’s home as his new roommate (and checks the Waiter’s mom into a “bang ’em and bin ’em joint” AKA a super cheap retirement home).
3) Liam McPoyle (Jimmi Simpson)
We meet quite a few members of the inbred McPoyle clan throughout It’s Always Sunny‘s run. For the most part, though, we stick with Ryan, Liam, and Margaret.
Liam is the best of the bunch, primarily because of Jimmi Simpson’s performance. He’s hilarious in the role, and another scene stealer in season bloopers. His off-kilter line readings are fantastic, as is his way of describing his horribly inbred family as “legions of us thousands sturdy…our bloodline was as pure as the driven snow.”
2) Waitress (Mary Elizabeth Ellis)
The Waitress (Mary Elizabeth Ellis, real-life wife of Charlie Day) has been with It’s Always Sunny from the very beginning. Literally the very first episode. And, from the earliest days, the core of her character is that she can’t stand Charlie, which is just perfect.
Ellis has appeared in every single season of Sunny thus far, and that’s unlikely to ever change. Even when the Gang went to Ireland in Season 15, there she was. Were it not for one other individual, she’d be the number one It’s Always Sunny supporting character.
1) ‘Rickety Cricket’ (David Hornsby)
Like Mary Elizabeth Ellis, David Hornsby has been a long-running and integral part of It’s Always Sunny. In fact, starting in 2008, he became an executive producer.
But that EP credit is not the reason his Matthew ‘Rickety Cricket’ Mara is number one here. No, it’s because that character has easily undergone the biggest transformation of any character on the show, and each and every step of that awful transition (from priest to PCP-smoking homeless man) was the Gang’s fault. And they will never, ever accept a shred of accountability for that.
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