Top 10 Awkward Moments in It's Always Sunny in Philadelphia

It’s not often that this show makes us feel sympathetic for the gang, but this is a rare exception. After the car crashes while they’re on their way to Atlantic City, a dressed-up Dennis and Charlie get picked up by a particularly horny truck driver played by a wonderful, and surprisingly cast, Tom Sizemore. What follows is some top-shelf cringe, as the trucker uses some graphic terminology to describe his sex life, while Dennis and Charlie desperately try to convince him that they are not, in fact, male prostitutes - otherwise known as lizards. You know the situation has taken a hard left turn when Dennis and Charlie seem like the normal ones.

If there’s one thing we absolutely NEVER want to see, it’s Frank Reynolds having sex. Unfortunately, that’s exactly what we got in the Gang’s version of “Lethal Weapon 5.” We watch Frank’s very awkward and protracted scene, complete with grunts, ugly pleasure faces, and the actress breaking character to tell Frank to “finish already.” It’s explicit, it goes on forever, and it’s hilarious to consider that Frank was actually sleeping with the woman. The gang made a porno, and even they are ashamed of it. To make matters worse, this sexually graphic and incredibly racist movie is played for Dee’s high school students. Suffice it to say, she was quickly fired.

While trying out a fancy new hipster bar, the gang gets into a loud argument and are shushed by a patron. This naturally sends Dennis into a red-hot frenzy, and so the next day, he and Charlie visit a police station where they fake an assault charge to get a facial composite of the shusher. This plan goes completely off the rails once Charlie accuses the shusher of raping Dennis. Glenn Howerton is delightful in this scene, as he expertly nails Dennis’ frustration, not necessarily with Charlie’s offensive improvisation, but at having to be the one who was raped. Meanwhile, Charlie Day is desperately trying to keep it together, and we don’t blame him. Even for “Sunny” standards, this is a ridiculous and gloriously uncomfortable situation.

The High School Reunion two-part episode is all about the gang’s misconceptions. While they believe themselves to be cool and important, the reunion serves as an unfortunate blast of reality that should have humbled their enormous egos. Of course, it doesn’t, and it all culminates in a horrifically embarrassing dance sequence in Part 2. The gang sees themselves as perfectly choreographed dancers who are performing to loud music, enthusiastic cheers, and a spectacular light show, when in reality they’re just flailing around on stage in front of a barely audible speaker. It’s a perfect visual representation of the gang’s delusions of grandeur, and it serves as a fitting cap to the episode’s bleak themes.

Watching failed stand up is always good for a cringe, even if it’s fictional. In the fourth season episode Dennis Reynolds: An Erotic Life, Dee performs some “stand up comedy” at the Laff House. It goes about as well as you’d expect – she greets the crowd with “howdy howdy howdy,” stands in a hunched position, fails to tell a single good joke, and nervously gags directly into the microphone. It’s a brilliant showcase of Kaitlin Olson’s gift for physical comedy, as her odd stance, constant fidgeting, and wavering voice hilariously convey Dee’s nervousness, while her stomach-churning dry heaves are pure comedy gold - for home viewers, that is. No one in the cast arguably does awkward humor better than her.

This is the gang at their worst. Well, maybe not, but it’s certainly up there. In this episode, they break into a house to steal an expensive vase. However, they get trapped and spend the rest of the episode trying to evade the family. That is, until Dennis grows frustrated and decides to waltz right out the front door. First, Dennis, Dee, and Charlie awkwardly stand in the doorway. Then Mac bursts in pretending to be a plumber. And THEN Frank comes out of nowhere and proceeds to accidentally break the vase with his whip. This is a wonderful example of how important gradual escalation is to cringe comedy, as the situation keeps getting worse and worse until it culminates in a literally explosive finale.

Someone give Glenn Howerton an Emmy already, because this man is a treasure. Here we watch Dennis putting the “implication” into effect as he tries to hit on a young woman on a cruise ship. He performs all the moves from the creepy serial killer handbook, like cornering her in a tight hallway, preventing her from escaping, and proudly stating that he’s been following and watching her. Howerton plays the faux charming, Bundy-esque creep to absolute perfection, and his performance, the creepy music, and the tight shots all combine to create a feeling of impending dread. It’s hilarious, but also a little terrifying. In a good way, as Dennis would say.

We’ve all had our fair share of bad dates. Just be glad that they weren’t this bad. In order to distract Charlie from the Waitress, Dennis and Mac set him up on a blind date. And to their credit, they do pick a nice restaurant. Only, Charlie sweats profusely, bleeds, says that he’s a “full-on rapist,” and orders a milk steak with a side of raw jellybeans. This is another perfect example of escalation, as it all culminates in Mac suggesting that he tells her he wants to have sex and Charlie violently grabbing his date’s breasts. It’s certainly painful to sit through, although you do have to feel at least a little sorry for Charlie. The man is trying. He’s just…not fit for dating.

Those six words are enough to give anyone nightmares. To the surprise of absolutely no one, Frank makes a complete mess of his hosting duties. He dresses like a mortician, repeats MULTIPLE times that he is definitely not attracted to the children, and accidentally states while his mic is on that he wouldn’t mind if his mortician stylist ate or had sex with his corpse. Everything about the pageant sequence is a cringe-inducing disaster, and it proves this series’ bold and respectable penchant for taking risks and pushing boundaries. How many other shows would have the gall to do something as brazen and inappropriate as this?

Before we cringe at our top pick, here are a few honorable mentions.

Uncle Jack
“The Great Recession”

“We Jizz in the Drink...”
“The Gang Tries Desperately to Win an Award”

Fake Baby Funeral
“Sweet Dee Gets Audited”

Brian LeFevre
“Frank’s Back in Business”

Charlie Proposes to the Waitress
“The Nightman Cometh”

If you thought Frank hosting a child beauty pageant was bad, you haven’t seen anything yet. After Dee is called a stripper’s “rock bottom,” she retaliates with what is arguably the darkest scheme in “Always Sunny” history - and that’s certainly saying a lot. While she pretends to get the down-on-his-luck stripper back on his feet, she actually arranges for him to strip in front of his own daughter, and the results skew into the macabre. She effectively ruins both of their lives, and even Dennis admits that the plan was depraved. Just when you thought that the characters couldn’t get any more inappropriate and deranged, they go and do this. We’re not sure if we should be amazed or horrified.