We Ranked The 19 Best Recurring Characters From ‘It’s Always Sunny In Philadelphia’ To Celebrate The Newest Season

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On Wednesday night, the fourteenth season of It’s Always Sunny in Philadelphia kicks off and it will officially become tied with The Adventures of Ozzie and Harriet for the longest-running live-action comedy in the history of television.

For the most part, the show’s success and longevity can largely be attributed to it’s five main characters and their various adventures (and misadventures). But, you know, it truly does take a village and part of what has made the show so much fun are the characters that orbit those main characters; the characters whose lives have been ruined by them or (at the very least) partially damaged.

All who enter Paddy’s Pub are lost.

Surprisingly, the list of minor and recurring characters on It’s Always Sunny isn’t as long as you’d think it would be given how long the show has been running. But that doesn’t mean we can’t find 19 to rank.

19. Rex

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Rex first entered the Sunny universe back in season four when he competed to be the new face of Paddy’s in “America’s Next Top Paddy’s Billboard Model Contest.” Sadly, he didn’t win, but his consolation prize was four more appearances on the show.

That’s what you get when you most likely have a bird that just won’t quit.

Two seasons later, Rex showed up when The Gang was trying to figure out who got Dee pregnant, where he was a suspect because Dee had berated him into sleeping with her. A few seasons later in “The Gang Saves the Day,” Rex appears in Mac’s fantasy version of heaven; a heaven that is filled with jacked dudes and a jacked God.

Mac is nothing if not consistent.

Later on, Rex poses as a cult leader in “Ass Kickers United: Mac and Charlie Join a Cult” and in season thirteen, he tags along with The Gang as they all head to the Super Bowl.

Again, it pays to have a bird that just won’t quit.

18. Principal MacIntyre

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As a principal, part of your job includes hiring people and anyone who has ever hired people knows that for the most part, that joint is a crapshoot. For every winner you get, you’re more than likely to snag a couple duds. It’s a law of averages type thing. If you’ve done it, you know what I’m talking about.

Principal MacIntyre gets it.

He had the misfortune of hiring Dee to teach acting and Charlie to be the school’s janitor in season six’s “The Gang Gets a New Member” and “Dee Reynolds: Shaping America’s Youth.” He probably didn’t think that when he hired both of them they’d end up bringing Dee’s students to Paddy’s to watch Lethal Weapon 5, but that’s exactly what happened and no matter what school district you’re in, that kind of move will get you fired real quick.

The funny thing about working in education is that if you’re tenured, they really can’t fire you. You can get transferred though, which is what happens to MacIntyre, and that’s why he’s at the middle school Charlie and Mac stop by three seasons later in “Gun Fever Too: Still Hot” with an offer to protect the school’s students.

You can’t help but wonder what school he’s at now.

17. Schmitty

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Whenever The Gang looks back and thinks about the old days, there are but two guarantees that come with it. The first is that their recollections are most certainly tainted and lacking accuracy and the second is that the person they are reminiscing about most likely doesn’t talk to them anymore.

As far as Schmitty goes, he was the fourth member of The Gang back in the day and was even roommates with Charlie before a disagreement over Night Crawlers got between them.

The end result was The Gang moving on but in season six’s “The Gang Gets a New Member,” the Gang (minus Charlie but plus Frank) decide to reconnect with their old friend. They do so with much pomp and circumstance, as is their standard operating procedure at times. Yet when Schmitty makes light of their ways, they lash out (which is again their standard operating procedure at times) and give him the boot again.

Schmitty shows up briefly a season later at the end of “The High School Reunion, Part 2: The Gang’s Revenge” as he swoops in and takes a drunk Waitress home with him.

Schmitty!

16. Luther MacDonald

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Mac and his dad don’t have what anyone would call a “loving relationship”—at least not a loving relationship that goes both ways. Mac wants to bond over a game of catch. Mac’s dad wants to bond by having his son smuggle heroin in his ass. Fairly routine stuff.

Luther has been somewhat of a regular on the show as far as recurring characters go, having appeared in eight episodes and being mentioned in another (“The Gang Goes to Hell: Part Two.”)

There was the heroin smuggling thing before he was out on parole only to be put back in jail thanks to Mac’s imagination. He was up for parole two seasons later, prompting Mac and Charlie to fake their own deaths.

In the Christmas special, we learn that growing up, Christmas for Mac’s family involved stealing other people’s presents.

Luther also appeared in the season thirteen finale as the intended audience for Mac’s interpretive dance representing Mac coming out.

He was not as moved or impressed as Frank was.

15. Da’ Maniac

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If you want to honor the troops, putting on a wrestling match for them is obviously the way to go. Everyone knows that, which is why The Gang does exactly that in season five’s “The Gang Wrestles for the Troops.”

They’re intent on making it legit so they bring in a real wrestler, Da’ Maniac (played by real-life wrestling legend “Rowdy” Roddy Piper.) He taught them some tips and really got to like the guys before a string of unpaid parking tickets got him arrested.

That’s, like, so Philly you don’t even know.

Da’ Maniac would be back, though, although not in the ring. He popped up in season nine (“Mac and Dennis Buy a Timeshare”) as The Gang was dabbling in pyramid schemes. Da’ Maniac wanted in, despite not totally understanding what “in” was.

You can’t blame him for the misunderstanding though. Those head injuries really catch up to you after a while.

That doesn’t affect his work performance, though. Dude became Invigaron’s top seller by the end.

14. Roxy the Prostitute

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When he joined The Gang, Frank was down to experiment; to live life on the fringes and embrace the life he felt had been stolen from him by his [insert synonym for “prostitute” here] wife. Frank wanted that single life and all the glorious trappings that came with it.

Yet by the start of season seven, Frank was looking to settle back down and felt he had found the woman to settle down with: Roxy.

Was Roxy marriage material? Definitely not. The Gang tried their best to convince Frank of that (albeit unsuccessfully) but Frank wanted love and he found love with Roxy. It was sweet.

Then she died of a crack overdose.

It just wasn’t meant to be.

13. Ben the Soldier

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In the same episode that The Gang meets Da’ Maniac, they also meet Ben the Soldier, who had come back from a tour of duty and was anxious to meet Dee, who he had been corresponding with. Dee ghosted him at first but at least he got a sweet pair of jean shorts.

Jean shorts: the gift that keeps on giving.

Ben and Dee dated for a bit (once she was able to confirm that he wasn’t handicapped) but he eventually broke up with her because she’s “a mean person,” which is accurate. He also did this with his face painted like a lizard but that’s neither here nor there.

Later on, he was a suspect when they were trying to figure out who had gotten Dee pregnant, was a target when they were trying to sell both Invigaron and a piece of a timeshare and, most recently, a member of the crew that went to the Super Bowl.

And he did it all with jean shorts on.

12. Special Agent Jack Bauer

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No, not that Jack Bauer. This is Jack Bauer the junkyard cat who can’t be killed.

It’s true.

Special Agent Jack Bauer, the feline Dennis finds in “Bums: Making a Mess All Over the City,” was allegedly born in a pool of gasoline on a rusty piece of scrap metal. According to word around the junkyard, he also once jumped through barbed wire into a vat of hot tar.

This cannot be confirmed or independently verified but it definitely seems like something he’d do. At the end of the episode, he jumped into a car doused with gasoline that then exploded and escaped unharmed.

The world is safer with him out there.

11. Charlie’s Mom

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She’s a sweetheart, but like a lot of us, she has some baggage. To be fair, her baggage is a past of reckless sexual episodes and a failed abortion, so that may make her slightly different than the rest of us.

One of those sexual episodes was with Frank and may or may not have resulted in Charlie, although at this point it’s really hard to keep track anymore.

She digs convicts (i.e. Luther), doesn’t much like fancy boys (i.e. Dennis), has a touch of OCD, a smidgen of racism and xenophobia and a morsel of self-esteem issues.

She also faked having cancer at one point because literally every character on the show is horrible in one way or the other.

10. Gail the Snail

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Guys, Gail just wants to party. She’s a woman now.

Let’s do it.

Just know that if things get weird, then you know what to do.

Does it make sense? Of course not.

But hey, it works.

9. The Waitress

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What’s her name?

No one knows. At this point, she might not even know. That girl has really fallen to pieces over the course of the show’s run. Her fall hasn’t been the most dramatic (standby for that one) but it’s been a hell of a descent into despair nonetheless.

Is it all because Charlie is infatuated with her? No, of course not. Yet is that part of the problem? Eh, maybe a little.

Our girl’s résumé is what those in the HR field would most likely call “a complete dumpster fire of a C.V.”

She started out as a coffee shop waitress then moved onto a corporate gig with a chain restaurant only to get fired for hiring Mac, Dee, and Dennis. If only she had had tenure (am I right, Principal MacIntyre?).

After that? Kind of a rough go. She was a carnival worker and then (most recently) a delivery girl. She’s also relapsed hardcore into drunkenness.

It’s still not the biggest drop off by a recurring character.

8. The Lawyer

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Here’s yet another member of the extended Always Sunny universe who is nameless and only known by his profession. The fact that The Gang flat out refuses to learn some people’s names isn’t the worst thing about them but it’s easily a sneaky top ten candidate.

The Lawyer entered their lives in season three when he was the executor of Dennis and Dee’s mother’s estate. To be clear, he was not the one dispensing items of the estate. He was essentially a middle man.

 

Over time, The Lawyer became a recurring foil for The Gang—especially Charlie, who fancies himself a lawyer (specifically one specializing in Bird Law).

The Lawyer also maneuvers his way into snagging the rights to Charlie’s Kitten Mittens idea, represents Maureen Ponderosa in her pre-cat days during her divorce from Dennis, and encourages Dennis and Dee to pull the plug on their comatose Nazi grandfather.

You’d think he comes out on top here, but nope. In season eleven’s “McPoyle vs. Ponderosa: The Trial of the Century,” the good lawyer gets one of his eyes gouged out by a bird.

There are no winners in It’s Always Sunny in Philadelphia.

7. Mac’s Mom

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She is but a ray of sunshine in a dark, dark world.

It should be noted that the world is so dark because of the cloud of cigarette smoke that constantly engulfs her.

Did you know she was once a Jiffy Lube attendant? I didn’t know that.

I guess you learn something new every day.

6. Maureen Ponderosa

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Bear with me here because there are a few Maureen Ponderosas.

Maureen Ponderosa With the Dead Tooth was the person who we first met in season six and learned that she dated Dennis in high school. Upon reconnecting, they got married. It was very sweet but then, you know, she started rocking a lot of cat sweaters and things went downhill from there.

Maureen Ponderosa With the Diamond Stud Tooth showed up at The Gang’s high school reunion; she was able to sport her flashy new bling thanks to the alimony Dennis was paying her after the divorce.

Maureen Ponderosa With the Boob Job was set to marry one of the McPoyles but the wedding descended into chaos courtesy of some well-placed bath salts. Amidst the chaos, Dennis and Maureen had sex instead of what was Dennis’ true intention, which was getting her to sign an agreement that would absolve him of any financial obligations now that she was married.

Maureen Ponderosa With the Cat Situation came along later and had gone through several plastic surgeries to make herself look like a feline. A season or so later, she had started acting and dressing like a cat.

Again, no winners on It’s Always Sunny in Philadelphia.

Unless, of course, you think a human attempting to become a cat is a winning situation.

5. Jack Kelly

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We all have something that we’d like to change about ourselves. Me personally? I wish I was, like, three or four inches taller.

Jack Kelly, Charlie’s uncle, longs to have larger hands. He is incredibly ashamed of his hands, which he believes are too small. He has hand-envy and his obsession has led him to take some unusual steps to make it appear as if his hands are larger than they are.

Two words, Uncle Jack: zip ties. If you’re going to try and pull off fake hands, you should zip tie them on. Zip ties are the best and you can also consider this a personal endorsement of zip ties.

Sweet Uncle Jack is also a terrible lawyer. He biffs it on Dennis’ divorce and he proves detrimental to the cause when it comes to Frank’s championing of gun rights because of his insistence to talk about pictures of kids.

Yeah, Uncle Jack might also be a pervert and he may or may not have molested Charlie at one point.

Other than that, great guy!

4. The McPoyles

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There are so many of them. And they’re all effin’ weirdos! How do you pick one over the other?

I’m lumping them all together and feel fine about it. It makes sense too. When it comes to Liam and Ryan, you never see them apart except briefly when it looked like Ryan was going to marry Maureen. But then, you know, bath salts derailed that whole thing.

Their sister Margaret is usually not far behind, even when it comes to staging a kidnapping.

In “The Gang Gets Invincible,” we met one of their brothers, Doyle, when Dennis, Mac, and Dee were all trying out for the Eagles. His playing career was cut short when Frank, who was tripping balls, shot him in the leg.

In “McPoyle vs Ponderosa: The Trial of the Century,” we were introduced to a whole slew of McPoyles— including Pappy, who capped off the trial by commanding his bird, Royal, to attack The Lawyer’s eye.

I think that helped break the trial wide open but, you know, once a lawyer in the case gets his eye gouged out, all bets are off.

3. Artemis

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I’d have to think you’re likely to meet some real wild cards in an acting class. I don’t think any of them would be as off the rails as Artemis but you might get close.

Dee met Artemis in acting class back in season one, and by season two, they were attempting to perform street theater outside of the bar. From that point on, she proved herself pretty useful to The Gang, whether it was helping make sense of the musical Charlie wrote or assisting with the mystery of who pooped the bed.

She also got into a really weird (and sometimes unsettling) relationship with Frank.

She also appeared in one of The Gang’s versions of Lethal Weapon, participated in a burlesque show at the bar when they were trying to win an award, and handled the soundboard when Frank felt it’d be a good idea to hold a children’s beauty pageant.

Long story short: find yourself a friend like Artemis.

Get close but, like, not too close.

I feel like that’s just best for everyone involved.

2. Bill Ponderosa

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Bill’s fall from grace doesn’t best that of The Waitress (although he comes close).

At this point in the show’s run, it feels like Bill has been around forever but he didn’t come around until season six when he started having an affair with Dee—an affair that ended his marriage. The funny thing about old Bill Ponderosa is that Dee was actually the second woman he was having an affair with at the time.

And you wonder why his wife got so pissed, huh?

After that, it all went downhill for Bill.

Booze, drugs, more drugs, more booze, hanging out with Frank too much, making Frank his AA sponsor, contemplating killing himself, more drugs, and more booze.

The aforementioned bath salts from his sister’s wedding? Yeah, those were courtesy of Bill, who dumped them into the milk, which is something to consider the next time you’re complaining about how one of your siblings ruined your wedding.

1. Rickety Cricket

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Quick, can you tell me Cricket’s real name?

I can give you a minute.

Don’t remember, do you? Of course you don’t. And that’s fine! It’s Matthew Mara, but that’s all in the past, man. He’s Cricket now and forever.

He’s also the one whose life has been ruined the most by his inclusion in the It’s Always Sunny universe.

He was a priest when we first met him (and a good priest at that).

But then it all came crumbling down.

After he was led to believe that Dee would be with him if he left the priesthood and found out that she actually wouldn’t, Cricks became homeless and eventually a drug addict. From there he weaved himself in and out of the show’s plots, whether it was to be hunted by Mac and Dennis or to get busted at the high school reunion for trying to steal people’s jewelry.

My dude lost teeth, got his face partially burned, and had sexual relations with dogs.

He maintains a sense of standards, though. And that’s admirable.

Terrible standards, but standards nonetheless.

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