It’s Always Sunny: Whose Lives Do The Gang Ruin The Most?

The sunniest people on earth meet lots of interesting characters - here's the ones whose lives they ruin most comprehensively.

it's always sunny in philadelphia

It’s said that we’re all lying in the gutter, but some of us are looking at the stars. The Always Sunny gang, bluntly, are not. They are far happier to wallow in their weird puddle somewhere on the fringes of society proper, bickering, eternally bickering. In ‘Paddy’s Pub: The Worst Bar In Philadelphia’, a reviewer they’d kidnapped (a crime which draws jail sentences in the decades) didn’t press charges on the basis that having to live with each other was a greater punishment. But his viewpoint was, understandably, coloured by his ordeal. The gang have a weird kind of equilibrium – and, very occasionally, prove that they love each other deep down.

All other homo sapiens on the face of the planet do not enjoy a stable role in the gang’s small, strange ecosystem. Most get chewed up and spat out, and even the occasional few who manage a victory over the gang find it Pyrrhic at best – invariably doomed to find themselves wondering whether it was really worth it. When another human being crosses their path, it is not a question of whether they’re going to get done over, but one of how badly they’re going to get it – so we’ve attempted to work out who the Always Sunny gang have done over the worst.


10. Principal MacIntyre

As a result of the gang’s action thriller Lethal Weapon 5 inspiring a student to black himself up, the principal loses his position at the local high school and gets relegated to a junior high. It’s a relatively tame punishment given that he was unthinking enough to hire Charlie and Dee in the first place – Charlie, for all his flaws, actually has experience as a janitor, but trusting Dee with children is downright dangerous. At least when Mac and Charlie show up later at the junior high, all they do is annoy him and wreck up his office a bit. Honestly, the guy’s getting off pretty easy.


9. Bill Ponderosa

The start of Bill Ponderosa’s downward spiral can’t really be laid at the gang’s door. Yes, Dee knew she was sleeping with a married man, but he was having affairs before her, so he was almost certainly going to lose his wife and children anyway.

Frank deserves a lot more of the blame, having served as Pondy’s AA sponsor through the curious, nigh-paradoxical method of keeping him clean by promising drugs later. And, when it came down to it, the gang were all perfectly willing to help him drink himself to death – as well as claim on his life insurance policy when he finally popped it. Pondy himself was utterly blasé about all of this, which doesn’t make it any better, but you can’t tell me it doesn’t make it any funnier.

By extension, Pondy’s son (“I call him Mr. Cocksucker, because he sucks so many cocks”) and daughter (“He said I was too fat to be a slut”) easily merit an honourable mention here.


8. The Juarez Family

The gang’s time with the Juarezes illustrated nothing quite so well as that even if they’re trying to help you, it’s going to go terribly badly. Probably the best that can be said is that – surprisingly – nobody was seriously injured.

In a display of pure altruism, or as close as the gang have ever managed, they took it upon themselves to fix up chez Juarez. What this actually involved was them kidnapping the family, getting them into thousands of dollars of credit card debt, inviting the neighbourhood to steal everything they owned, and ultimately burning the house down. The gang did avoid criminal charges, but only through a wild plea bargain where they handed the Reynolds mansion over to the Juarezes.

As if this ordeal wasn’t enough, there’s one final sting in the tail. While trespassing on their old grounds, Frank and Dee ran into Mr. Juarez once more. He didn’t seem to begrudge them his ordeal, as he’d since suffered a greater indignity at the hands of his adoptive country. Thanks to property taxes, he’d been forced to give up the mansion – and was only there working as a gardener.


7. The Lawyer

They go tit-for-tat, they jabber-jaw, and at the end of the day – well, bluntly, he’s a much better lawyer than Charlie by dint of being a) an actual, qualified lawyer and b) fully literate. But, as mentioned in the intro, getting the better of the gang is like feasting upon the fruit of a poisoned tree. The lawyer steals the rights to the Paddy’s Pub merchandise, gets a restraining order against the gang, slams Dennis with punitive alimony payments – and yet, having lost his wife and probably gained an ulcer, these successes must taste like ashes in his mouth. Especially since, despite the restraining order, he still has the gang abruptly turning up at his office every so often.

One of his court battles with the gang actually led to him losing an eye, but this physical injury can’t possibly have stung quite so badly as the fact that it came alongside Charlie presenting a halfway credible counterargument, finally displaying his expertise in the little-known field of bird law.


6. Bryan LeFevre

An odd entry, this, since Bryan’s death isn’t really on the gang. If he left his ID in the bar, and Mac wouldn’t let him back in without his ID, while it’s a horrible catch-22 it’s hardly Mac’s fault if the guy then gets stabbed to death by a crackhead. And yes, due to a slight mishearing, when Charlie visited the morgue he ended up cutting off Bryan’s finger, but while this is a crime it’s not like it’d bother him too badly at that point.

Bryan’s fate only takes a turn for the morbid after he’s dead, and they won’t let his spirit rest. Dennis steals his identity – not in the ‘bank fraud’ sense, but in the more visceral sense of stepping into Bryan’s shoes and living his life, or, as Dennis puts it, “wearing another man’s skin”. His exploits as Bryan LeFevre have, by the show’s count, resulted in the torpedoing of a multi-million-dollar business deal, and at least one child growing up without a father – misdeeds which will ultimately be laid at Bryan’s door. Even the release of death and the solemn calm of the grave is no protection from the gang doing you over.

(There’s also an out-there but amusing fan theory that it was actually Dennis who killed Bryan in the first place.)


5. Maureen Ponderosa

Initially, Maureen seemed to have made a fairly clean break after her ordeal with the gang. Dennis fucked her and then he chucked her, no argument, but that’s Dennis’s standard method of operation, and their subsequent divorce was if not amicable then certainly mutual. Compared to the average victim of the D.E.N.N.I.S. system, Maureen got off incredibly lightly.

Dennis then derailing her next marriage – a relationship which didn’t so much not take off, as explode in the hangar – seems to have been far more damaging. It was only after this that Maureen’s cat obsession, before then seemingly just a marker of twee woman-childness, transmuted into her actually becoming a cat through a series of dramatic surgical procedures. While it’s very much up in the air how much Dennis’s involvement actually caused this, by all accounts it was his alimony payments that funded the surgery, so he’s at least culpable on that level.

Maureen ultimately meets her fate when, while ‘prancing about on the roof like an asshole’, she falls off and breaks her neck. While her cat identity was a big part of this, you can’t really say that Dennis killed her – no matter how much Mac and Charlie tried to spin it that way.


4. Luther Macdonald

An odd choice perhaps, given that Luther – aka Mac’s dad – is one of few people who can inspire a healthy mix of respect and fear from the gang, and, like Dr. Krieger before him, has what can only be described as a naturally evil face. Per the man himself, “I don’t blink”.

But even though he’s a convicted drug dealer, when you look at his actual interactions with the gang, he comes off a lot better. The worst he’s ever actually done to them is ask Mac and Charlie to smuggle heroin rectally – not exactly Mr. Rogers behaviour, fine. But on the other side of the coin, Mac and Charlie perjured themselves to try and get him denied bail, and would later go on to interfere in a murder investigation, trying to prove Luther innocent but mucking it up so badly that he got branded a snitch instead. He appears in later episodes, so we know he wasn’t actually killed over this, but presumably that’s only because he was quicker with the shank.

The tragic underlying arc here is that Mac has always been desperate for his father’s affection – and, as we see now and again, Luther really does love his son, or at least he did before having his life quite so comprehensively ruined.


3. Unnamed Golf Fan

Just to clarify, this is the poor devil Frank and Dee end up mistakenly spying on instead of Dennis and Dee’s biological father. The gang’s fumble-fingered attempts at espionage – and at selling gasoline – result in them crashing into the guy’s car, repeatedly, and then blowing it up. He becomes convinced that someone’s out to get him, and, in a true cry of despair, declares to the world “I loved that car!” – because, sad to say, he doesn’t have much else.

Fortunately, the gang don’t stick around to try and make up for this – something which could only have gone poorly – although they later accidentally invite him to Thanksgiving dinner, and it turns out he’s lost custody of his kids due to his “horrible drug problem”. This is nothing to do with the gang, but it still feels very much like kicking him while he’s down.

In fact, that could summarise unnamed golf fan’s whole arc in the show. He entered the gang’s orbit due to a case of mistaken identity, through sheer cruel fate. Unlike the rest of this list, he’s done nothing to draw the maelstrom that follows the gang, he has no connection with them and doesn’t even know their names. But in the red-in-tooth-and-claw world of It’s Always Sunny, even that cannot save you.


2. The Waitress

Unlike most of the previous entries, you can’t really claim that her severe personal problems would have happened with or without the gang. Anyone subject to both Charlie’s stalking and Dennis’s manipulative charms would at least consider hitting the bottle and not stopping. And speaking of not stopping, when the waitress fell off the wagon, it was almost entirely a result of Dee attempting to live out her deranged Sex and the City fantasy.

Charlie’s obsession with the waitress is, perversely, something of a double-edged sword. As we saw when he got a girlfriend and stopped following her around, barking at anyone who might have tried to steal her bike, her life actually got markedly worse without him – although you could see this as her simply having become used to Charlie’s terrifying romantic overtures. It’d be like accepting that from now on, say, mice or dry rot is something you’ll just have to live with. What keeps it from being outright horrible is the sheer depth of Charlie’s delusion – his surveillance of her is Big Brother-scale, yet he can only conceive of himself as some kind of romantic, to the point of writing an entire musical as a roundabout way to propose to her.

The ultimate insult finally came when, after some ten years of stalking and abuse, Charlie wore her down into agreeing to have a child with him. Mere moments after he’d come, he discovered that he couldn’t stand her – and so the cycle of neglected children with screwed-up ideas about romance begins anew.


1. Rickety Cricket

There simply isn’t another contender for the top slot. Most of the other entrants on this list did, in some way, sow the seeds of their own destruction, like the protagonist of a Greek tragedy, but this one just seems to have angered God somehow. Matthew Mara – or Rickety Cricket, as most know him – has a history we believe is actually too upsetting to recount sans the comic timing of the show, and we do so here only with that proviso.

Even before the series started, Cricks was getting thoroughly done over by the gang. While they were in school together, the boys teabagged him and distributed pictures of him naked (funny how serious sex crimes get laughed off when it’s children doing it, isn’t it?) while Dee, for her part, ruthlessly exploited his helpless crush on her up to the point of making him eat a horse turd. But, with his profoundly awful childhood behind him, he studied hard, received a Masters degree in theology, and became a practising Catholic priest. At this point, he should really have never seen the gang again and spent a happy life puzzling over the mysteries of the trinity.

Over the length of one episode, Dee led him on enough that he renounced his priesthood to be with her, only to have her reject him. That alone would make him a contender for this list, but this is only the beginning.

The next time he crossed paths with the gang – by now homeless and begging on the streets – he ended up slinging cocaine for them, getting dangerously addicted to the stuff in the process, and then the Mafia broke his legs. This was the first of many serious injuries he’d suffer due to his relationship with the gang, and he’d go on to have his neck sliced open, get shot in the hand, catch an axe in his arm, and be horribly burned when Mac and Dennis’s apartment caught alight, as well as suffering a litany of other horrendous and degrading injuries that happened offscreen, mostly involving stray animals.

And yet there’s something of a happy ending here, as the process of becoming a homeless, drug-addled prostitute has allowed him to get on with the gang far better than anyone might have expected. All that degradation has, at last, brought him into their bizarre equilibrium, and there’s a kind of liberation in in reaching the point where you can rock up at the bar and merrily ask ‘you mind if I go in the bathroom and smoke some PCP?’. You do you, Cricket. You do you.

Check out our analysis of another woefully neglected Always Sunny character here.

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