In all the chaos of the show, it’s hard to imagine any of the characters having a moment of goodwill, but they’re there amongst all of the terrible and selfish actions the group has done individually and collectively over the years. Whilst some characters have behaved much worse than others, whether it’s to their friends, family, or the many random characters of Philly, it’s time to look at their ultimate best and worst moments.
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Whilst Dennis has been viewed as a borderline sociopath and quite possibly the worst of the gang with how he treats women throughout the show, his ultimately worst motive and moment comes from The Gang Buys A Boat (S6Ep3). From what has gone on to become one of the most recognized Sunny quotes, The implication is by far Dennis’ worst concept. The implication involves taking a boat and setting sail out into the middle of nowhere where you cannot say no to someone’s advances and there is no escape. From someone who has had tools in his car to security systems in his bedroom, the concept of the implication is Dennis’ most sinister moment and in the scene, even Mac is creeped out by Dennis’ idea and thinks it is very dark.
Dennis’ most redeeming moment on the show is when he feels he is able to step away from everything and grow up in Dennis’ Double Life (S12Ep10). The episode reveals that Dennis has a secret child in North Dakota and the rest of the gang aim to help him with his problem. After everyone’s poor attempts at helping and witnessing the madness that happens inside Paddy’s Pub, Dennis makes the choice of leaving the group and moving to North Dakota to be a dad. It’s a finale like this that kept fans guessing whether Glenn Howerton had actually left the show, making it one of the best-written shows on TV. Of course, Dennis would return the following season to bring the gang back together.
Where Mac is memorable for his good moments, especially one of the most iconic Sunny memes, his denial of his identity in earlier seasons creates some of his worst moments. In one of the earliest episodes, Charlie Has Cancer (S1Ep4), Mac falls for a woman who has yet to go through gender-reassignment surgery. Every future encounter is problematic such as in Mac Is A Serial Killer (S3Ep10) where he hooks up with Carmen but is embarrassed to tell the rest of the gang, and in Charlie Has Cancer he asks her if he can be the first person to sleep with Carmen once she has had her surgery. When the character returns again in Mac Fights Gay Marriage (S6Ep1), seeing that now Carmen is now married to someone else and never contacting him, Mac and his complete lack of understanding of the LGBTQIA+ community leads him to try and ban gay marriage.
The phrasing revolving around Mac’s sexual identity was a running theme in Sunny for many seasons, but Mac’s most shining moment is when he finally accepts who he is. Mac’s character is very conflicted with his dedication to his catholic religion, his identity as a homosexual man, and his everlasting desire to please his father. In Mac Finds His Pride (S13Ep10), Frank suggests Mac will never be comfortable with who he is until he comes out to his dad. What happens next is one of the most abstract and beautiful moments of the entire show. Mac performs an interpretive dance with a woman representing god with his father in the audience. In a show that is usually horrible to its characters, the dance of Mac coming out is beautifully choreographed and displayed. Even when Mac’s dad walks out, it is almost as if Mac expected this, and the torment he feels is shown further into the dance.
Charlie Kelly is no doubt the most-loved character from the show and is certainly the least intelligent of the lot, but his heart is mostly in the right place. Throughout the vast majority of the show, he is infatuated with The Waitress who continues to reject his advances, and whilst Charlie’s adoration for The Waitress is in the stalker territory, without him, her life isn’t the same. The Waitress is key to both Charlie’s best and worst moments in Charlie And Dee Find Love (S8Ep4). It is revealed Charlie has been helping The Waitress without her knowing such as protecting her bike, putting vitamins in her shampoo, and making sure her food isn’t poisoned. She asks Charlie to leave her alone and after Charlie agrees, but following this as there is no one to take care of The Waitress everything starts to go wrong for her such as her hair falling out.
Charlie Day plays a loveable character so well and has a voice everyone loves. The one time Charlie acts horribly is from the same episode after finding new love in Ruby. Dee and Charlie become associated with a well-to-do family but it is revealed Trevor who Dee was seeing was making fun of her. It is assumed by Dennis that Ruby was making fun of Charlie too and through his and Frank’s work, injure The Waitress who says to Charlie she needs him if he’s the reason bad things don’t happen to her. Charlie turns his back on Ruby by calling her a “Stupid Little Rich S*ut” which leaves Ruby devasted as she genuinely loved Charlie.
Dee is one of the most horrible characters in the show, but she is certainly the one at the butt of most jokes. Whilst all of the group are responsible for the downfall of Cricket at different stages, it is Dee that started his descent into homelessness. Otherwise known as Matthew Mara, in The Gang Exploits A Miracle (S2Ep7) Cricket was a priest who had had a crush on Dee in high school and after reconnecting with the group in a bid to bless their ‘religious stain’ in the bar, Cricket refuses Dee’s flirty tactics. After Dee is blamed for not getting Cricket to bless the stain, she seeks revenge and tells Cricket she is in love with him. Cricket leaves the priesthood to tell Dee he loves her only to be rejected by Dee and is unable to return to the priesthood. Cricket’s life then turns into turmoil and is a recurring character in the show.
Usually, when an actress becomes pregnant they take time off from their job, however, when Kaitlin Olson became pregnant prior to filming It’s Always Sunny In Philadelphia’s sixth season, her pregnancy was written into the show. Most of the season was dedicated to finding out who got Dee pregnant and right until the end of the season, the gang have no idea. It is revealed after giving birth in Dee Gives Birth (S6Ep12), that Dee was a surrogate for Carmen who couldn’t have children. Dee’s selfless act of carrying a baby is very unlike her character and is a pleasant step away from the arrogant and angry Dee fans are well familiar with.
Frank has had a lot of crazy business ideas throughout the show and it’s no doubt that Danny DeVito does some of the weirdest and most memorable things for Sunny. Whether he’s crawling through sofas, getting stuck inside playground rides, or gurgling beer in an unsatisfactory manner, Frank has some of the worst habits. However, from a humane perspective, The Aluminum Monster vs. Fatty Magoo (S3Ep5) has to be Frank’s worst moment. Frank begins the episode manipulating Mac and says he can show him how to manipulate people. Charlie and Dee get involved in creating dresses in the seedy world of fashion production which ends up being run by Frank. Frank aims to break down Dee, Charlie, and the Eastern-European workers who are all working in Paddy’s Pub basement. Frank is basically a fascist leader at this point and is manipulating everyone around him.
One thing that’s guaranteed is Frank loves Charlie and it is suspected for a long time that he is Charlie’s father. Danny DeVito has played a variety of characters for nearly five decades, but his portrayal as Frank is one of his most iconic. Frank respects Charlie’s way of living which is unconventional and gives up his million-dollar lifestyle to be more like Charlie. The two have been roommates for many seasons and share a bed together which both are reluctant to give up doing. Whilst Frank hasn’t always done great things for Charlie including sleeping with his mother and The Waitress, at the same time when he thinks Charlie has died, he grieves terribly. The most wholesome moment between the two comes in one of the most controversial episodes The Gang Finds A Dumpster Baby (S3Ep1). When Frank and Charlie become dumpster divers and fill their apartment with trash, they take to living on the streets, and here it shows the two of them keeping each other warm as they sleep on the sidewalk. This small scene shows the relationship between the two who can’t live without each other.
In terms of its most wholesome or best moment as a group then that has to come from the finale of the most recent season. The gang’s adventures in Ireland were quite the shift from the normal setting of Paddy’s Pub but was the right direction for the show. The whole of Season 15 had featured commentary on 2020/2021 events and caused the cast to be as outrageous as ever. Over the course of the season, Charlie had met and developed a relationship with his father played by the great Colm Meaney (Star Trek) only for the character to die in the final episode. As a Kelly family tradition, the body of the deceased must be carried up a hill and tossed to the sea below.
The episode sees the gang starting off as a collective only to fall apart leaving Charlie to do the impossible job on his own. Eventually, the rest of the gang comes to their senses in their ridiculous patriotic way and together the group finishes Charlie’s dad’s last wish. It’s one of the few times the viewer can tell the gang really does care about each other, but at the same time if season 16 rolls around it’ll be like none of this ever happened. Season 15 ended in a way no other season has and it felt as though if that was it for It’s Always Sunny In Philadelphia many fans would be fine with that.
As a collective, it is hard-pressed to decide on the ultimately worst moment with highlights from the gang including the further downfall of Cricket, encouraging underage drinking in the bar, taking out life insurance on the suicidal Bill Ponderosa, kidnapping a bar critic, or the time they destroyed a family’s home. It has to be said that The Gang Gets New Wheels (S13Ep5) is the worst thing they have done as a group which involves crimes against children. The episode involves Charlie and Mac reminiscing about their bikes being stolen as kids and buying new ones, only to be faced by a new generation of bullies. Their eventual issue with the group of children results in Mac and Charlie beating them up, most likely killing one of the children.
After befriending a group of housewives, Dee is offended when she is called out on never being married. Dee seeks revenge and has sex with one of the woman’s ‘boy-toys’ who turns out to be her teenage son. This same teenage kid who Frank had said he would help get laid after showing him a load of ancient porn magazines. Dennis is the getaway driver for everyone after Mac and Charlie run away and Dee and Frank crash a car, and his calm exterior is unphased by all of the dark events that have happened. This episode isn’t considered to be the worst Sunny episode, but it certainly goes to depths that many don’t. If it involves children you know it’s going to be bad and that’s why this episode stands above the others.
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