Unlike most popular American sitcoms,It’s Always Sunny in Philadelphiacan at times be incredibly dark in tone. The repercussions of this darkness can also be quite far-reaching and often end up having a long-lasting and noticeable effect on not only the show’s main cast, but also on some ofits many excellent secondary charactersas well.
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Though this can sometimes come in the form of permanent disfigurements and missing body parts, most of the scars are the “on the inside” type. This does not mean that viewers can’t still see them though, with many of the characters' actions shaped by their past misfortunes. These are the unluckiest characters inIt’s Always Sunny.
5Ruby Taft
Though sheonly appears in a single episode, Ruby Taft is one of the more memorable side characters inIt’s Always Sunnydue to the appalling way in which the gang treats her. Unlike her brother, Trevor, Ruby is an honest and genuine young lady and one who has real feelings for Charlie. What exactly she sees in him is anybody’s guess, but for him to so brutally cast her aside in favor of a woman who still has an active restraining order against him must have come as a massive slap in the face for the young millionaire.
Charlie’s decision to use her to make the Waitress jealous is made all the more brutal by the very public manner in which his plot is revealed. He’s fully aware that Ruby has genuine feelings for him and yet is more than happy to break her heart in a crowded room that’s full of her family and friends. He’s also unnecessarily cruel about it, telling her that she lacks quality and calling her a “stupid little rich sl*t,” rather than simply breaking things off amicably. As Dennis quite rightly points out, Charlie had the cruelest intentions of all that day.
4Bill Ponderosa
For years after high school, Dee and Dennis saw Maureen and Bill Ponderosa as the ones that got away. When the prospect of reconnecting with her former crush suddenly presents itself in season 6, Dee is therefore very keen to grasp it with both hands. At least until she actually sees Bill, anyway. It turns out that he’s packed on quite a few pounds since the pair last saw each other, which causes Dee to wretch whenever she sees or even thinks about him. This doesn’t stop her from sleeping with him, however, nor does it prompt her to return theBMW3 series that he buys her as a gift.
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While there’s certainly nothing wrong withtwo single consenting adults hooking up, it’s soon revealed that Bill is not actually single. It turns out that he’s married with two kids and his most recent affair proves to be the last straw for his wife. The couple divorce and Bill falls into a deep depression that’s fuelled by a combination of self-loathing, alcohol, andlots and lots of drugs. Granted, most of Bill’s problems are of his own making, but there’s a strong argument to be made that Dee willfully served as the catalyst for the initial explosion.
3Liam McPoyle
If being strange or being inbred were crimes, then each and every one of the McPoyle family would be found guilty as sin. Bad things can still happen tostrange peoplethough and Liam has suffered his fair share of them over the past 15 years. Whether having to watch his brother Doyle get shot by Frank or constantly being insulted and looked down upon by everybody else on the show, he’s been through more than most, and most of this has come at the hands of the gang.
Perhaps the very worst thing that they ever did to him was depriving him of a chance at a normal married life by smuggling Ryan into the wedding venue. Having been raised as a McPoyle, life was always going to be difficult for Liam, but marrying Maureen could have helped him to turn his life around to some degree. Instead, the wedding ends with Dennis sleeping with Maureen and Liam’s eye getting pecked out by Pappy McPoyle’s Pocono Swallow.
2The Waitress
Despite her tough exterior, the Waitress is one of the moretragic charactersinIt’s Always Sunny. A lifetime of being ignored has led to her developing a rather nasty drug and alcohol problem that she still struggles to keep under control today. Even now, despite having known her for most of their lives, the gang still refers to her as the Waitress; including Charlie, who claims to be madly in love with her and has been stalking her since the show first began more than fifteen years ago.
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If havingan oddball like Charliebreak into her home and mess with her things weren’t already bad enough, she also has to contend with the rest of the gang as well. Dennis uses her like an object just to get at Charlie, while Frank takes advantage of her when she’s at her absolute lowest. Dee has also mistreated the character in the past, having goaded her into drinking despite knowing all about her problems with alcohol. It’s not just the gang either, with her ex-boyfriend Brad fake proposing to her in season 5 just to get back at her for dumping him in high school.
1Cricket
When Matthew “Rickety Cricket” Mara is first reunited with the gang in season 2, he’s a well-respected and well-adjusted man of the cloth. By the end of his first episode, however, he finds himself unemployed and becomes homeless not long after as a result. The gang then coerces him into selling drugs for them the following season, which leads to Cricket developing a serious drug problem as well. Sadly, things have continued to go downhill for the character since then.
The gang regularly uses Cricket as part of their plans and has subjected him to both physical and emotional abuse over the years. Among other things, they’ve shot him in the hand, sliced his face open in a wrestling match for the troops, andhunted him down like an animal. His appearance has also suffered quite dramatically during this time, with the left side of his face covered in burns due to the Thanksgiving fire at Mac and Dennis' apartment in season 9 and scars resulting from an off-screen street fight with a dog.
