Which It’s Always Sunny in Philadelphia Character Has Taken the Most L’s?

The Paddy’s Pub gang on It’s Always Sunny in Philadelphia are seen as many things – menaces to society, criminals, scum of the earth, sociopaths – you name it. But above all else, they are losers. Within every season, at least one member of the gang consistently eats crap. No, it’s not always their punching bag, Dee … well, it is usually but it’s not always. 

Every season each character experiences some degree of defeat. However, certain characters endure the brunt of the blow more frequently than others. As season 17 premieres, let’s review each batch of episodes and identify the biggest loser.

Season 1 – Charlie

Charlie Kelly faced some heavy blows in Sunny‘s inaugural season. Many of those revolve around his misfortunes in pursuit of the Waitress, among other things, like getting shot and landing in the hospital and learning about his … well, the episode in question is titled “Charlie Got Molested.” And to think this is faaaaar from him becoming the gross man he is now.

Season 2 – Charlie

Sunny‘s sophomore season continues the Rat King’s losing streak with his desire to have the Waitress growing even more intense. Charlie keeps getting pushback and rejections from her. This time, though, the Waitress goes after Dennis, and when she fails to get him, she ends up sleeping with Frank, which breaks Charlie’s heart in the famous installment “Mac Bangs Dennis’ Mom.” In addition to all of that, Charlie is hit by Dennis’ Range Rover and learns he doesn’t even know his father and assumes it is Frank. It’s okay. Charlie got answers later down the line …15 years later.

Season 3 – Dee

This marks the beginning of Dee’s transformation into a punching bag role. Season three sees her getting set on fire in the titular “Frank Sets Sweet Dee on Fire” and shattering knees in “The Gang Dances Their Asses Off.” It’s the start of a beautiful supervillain origin story.

Season 4 – Dee

Would you look at that? It’s Sweet Dee again. Expect a lot of her on this. In season four, Dee gets waterboarded in a urinal, has a heart attack, and has her sedan crashed by Mac and Charlie. 

Season 5 – Dee

Another one bites the Dee. Dee gets broken up with by soldier boy Ben, stabbed, her car stolen, stuck in the wall, and smashed in the head with a chair, breaking her nose. Five L’s for season five. A very not-so-sweet season for Sweet Dee, as per many seasons. 

Season 6 – Mac

Imagine being a major sports fan, very passionate about your city and its teams. Then you become the biggest jabroni of all. That’s definitely what happens to Mac in season six. While stranded in the woods with Dee and Frank, he has to resort to cannibalism. Meanwhile, Dennis and Charlie inadvertently land in Atlantic City and subsequently meet Mac’s idol, Philadelphia Phillies second baseman Chase Utley. Of course, Dennis rubs it in with a picture. Moreover, in “Mac’s Big Break,” he falls face first when having to make a winning shot at a Philadelphia Flyers game. Any sports fan would “Order 66” themselves after those two big blows like that. 

Season 7 – Mac

Mac got fat. That’s it. He became fat and was the butt of many fatphobic jokes. Everything else was incomparable.

Season 8 – Dee

Welcome back, Dee! While Dee didn’t face any physical injuries this bout compared to later and earlier seasons, the Gang did mess her up psychologically. Starting with “Charlie and Dee Find Love” where she gets cuckolded by Mac over the guy she’s into. Then, in “The Gang Gets Analyzed,” everyone crashes out on Dee’s therapist, who then berates Dee and tells her to do the dishes. Oh and Mac and Charlie total her car, AGAIN, in “The Maureen Ponderosa Wedding Massacre.” So much permanent damage for one angry flightless bird.  

Season 9 – Frank

Some of Sunny‘s running jokes that always make me laugh involve Frank going through hell in his birthday suit or undies. Season nine sees this happen TWICE! In “Mac and Dennis Buy a Timeshare,” he’s stuck in a jungle gym coil in broad daylight, in his undies, with no one to help him. In “The Gang Gets Quarantined,” he is discovered on the floor by the gang, covered in hand sanitizer, after contracting the flu and sent straight to the hospital. 

Season 10 – Dennis

Dennis gets a lot of five-star L’s because of his capital P pride during the season of the famous “I’M A FIVE-STAR MAN” crashout. There’s his entire online dating reputation being decimated in “The Gang Group Dates,” which brings us that iconic moment and one of Glenn Howerton’s funniest scenes. But additionally, the man gets diagnosed as being a psycho, which he is. Additionally, he makes a complete mockery of himself on national television in “The Gang Goes on Family Fight,” squirming and withering over the sound of a buzzer. Dee also humiliates herself in the same episode and suffers severe injuries in “The Gang Spies Like U.S.,” but Dennis’ entire character is hilariously destroyed for the majority of season 10.

Season 11 – Dennis

Season 11 continues Dennis’ losing streak as he takes three major losses in three episodes in a row. Well “Frank Falls Out the Window” isn’t so bad as he and Dee get their karma when trying to deposit a check from an amnesiac Frank, who they take advantage of, only for it to say 2005. But alas, the following episodes bode worse for the “Golden God” as he breaks his ankles while skiing against Charlie in “The Gang Hits the Slopes.” Then, in “Dee Made a Smut Film,” Dennis’s attempts to film his sex memoirs lead us to learn that the man was molested by his librarian in high school. A teacher who even Cricket thinks is gross. CRICKET! 

Season 12 – Dee & Dennis

The Reynold siblings share the crap load of season 12. Dennis has an entire unaired A&E-styled true crime episode about him potentially murdering his ex-wife Maureen. Upon his exiting Paddy’s in “Dennis’ Double Life,” the gang blow up his car with the rocket launcher Mac gifts to him a few episodes prior. As for Dee, she literally hits her lowest of lows in “PTSDee,” maliciously getting vengeance on a male stripper for calling her his “rock bottom.” Not before she embarrasses herself trying to make the boys laugh when she gets her head stuck in a banister and poops her pants in Dennis’ fake sitcom experiment within “Old Lady House: A Situation Comedy.”

Season 13 – Dee

In a season that sees Dennis “strangely” returning from his dramatic exit and Charlie being mutilated in service of the Eagles winning the Super Bowl – go Birds – Dee simply has a bad time. She falls out of the window after her titular “Ladies Reboot” of “The Gang Beats Boggs” goes belly up, and in “The Gang Gets New Wheels,” she sleeps with a minor, mistaking him for the boy toy of her middle-aged acquaintances, in an attempt to exact revenge for a trivial joke. Not a good year for Dee, for sure. But honestly, what year is it?

Season 14 – Dee

This season didn’t have many L’s because the gang is more of a threat to others and makes the world suffer. But in “The Gang Chokes,” Dee almost chokes to death, and no one intervenes. Granted the setup involves the same happening to Frank and Charlie spending the rest of the episode finding his way to make up for it. But when it happens to Dee, no one cares. She later loses all of her hair in “A Woman’s Right to Chop,” and a wig made of only dogs is used in its place. Plus, we learn in “Paddy’s Has a Jumper” she has envisioned ending it all. Understandably so. Being Deandra Reynolds is a biblical challenge. 

Season 15 – Dee

Dee did not fare well during the post-Covid season of Sunny. Charlie is a worthy contender, as we learn Dennis and Mac used Charlie’s savings to invest in Paddy’s Pub, and he is the rightful owner of the establishment, unbeknownst to him. Additionally, he loses his biological father, of whom he just met while in Ireland. Nevertheless, the episodes “Dee Sinks in a Bog” and “The Gang Replaces Dee With a Monkey” speak for themselves. A portion of the Ireland trip involves the gang hijacking her trip, losing a small movie role to, of all people, The Waitress, and then being run over and subsequently being driven in the trunk of a car. Dee’s life is full of such unfortunate situations, but this season was cruel to her, and we wouldn’t have it any other way for the funniest girlfailure bird on TV. 

Season 16 – Frank

Sunny season 16 saw the gang facing many losses. However, Frank gets the worst. Starting with the season opener “The Gang Inflates,” Frank learns that for 20 years there was a spare room. While at first he tries to use it, he is eventually manipulated by Charlie with a discontinued Teenage Mutant Ninja Turtles Pie snack to seal the room back up (and among other things), forcing him to stay in that bed with him forever. But in “Frank vs. Russia,” he experiences what may be the most hilarious and excruciating pain of all: being remotely controlled by anal beads while playing chess and writhing when he feels the bead’s power. Even as I write this, the thought still makes me laugh. It’s a pain I wouldn’t wish on my worst enemy, unless you like that kind of thing.

Final L Count

Dee – 8
Dennis – 3
Mac – 2
Charlie – 2
Frank – 2

New episodes of It’s Always Sunny in Philadelphia season 17 premiere Wednesdays at 9 p.m. ET on FXX.