The Most Hilariously Awful Moments


Following the wild and zany antics of a group of narcissistic and sociopathic pub owners, It’s Always Sunny in Philadelphia is a beloved fan favorite. The smash-hit FXX (formerly FX) sitcom made its debut in 2005 and has been delivering big laughs and crazy exploits ever since, and in 2021 the show became the longest-running live-action comedy series in America, while also finding new life and new audiences as one of the best series to stream on Hulu. Featuring the talent of amusing performers like Charlie Day and Danny DeVito, It’s Always Sunny is never one to shy away from pushing boundaries and embracing the outlandish.



Over the sitcom’s impressive 15 seasons so far, the gang of degenerates have found themselves in some truly outrageous situations, many as a result of their own greed and selfishness. From hunting humans to inappropriate musicals, steak contamination schemes and water park woes, the Philadelphia misfits have had their fair share of oddball misadventures. These are some of the most hilariously awful moments from It’s Always Sunny in Philadelphia.

9 The Gang Solves the Gas Crisis

The hilarious group of reprobates have concocted their fair share of get-rich-quick schemes, with their conniving plans almost always backfiring due to someone’s own selfishness or deceit. Mac, Charlie, and Dennis team up to solve the gas crisis in this episode, opting to steal Dee’s life-savings from her sock drawer after banks (rightfully) refuse to fund their business endeavor. The entertaining trio set out to sell the gasoline, going door-to-door in hopes of scamming their way to a lucrative profit but unsurprisingly yielding no results.

While the episode as a whole is full of sidesplitting moments like Frank waterboarding Dee in the men’s room urinal and the guys failing miserably at seducing a bank clerk, the funniest part is without-a-doubt when Charlie lives up to his “wild card” reputation and cuts the brakes of the van they’re all driving in, causing the gang to panic and ditch the moving car.

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8 Charlie Work

In the fan-favorite season ten episode “Charlie Work,” viewers are given a closer look at just how pivotal Charlie’s role is for the overall success of Paddy’s Pub, a fact that is proven when the gang learns a health inspector is coming for a surprise visit. The fast-paced, zippy episode has Charlie in the driver’s seat as he runs around the bar to make sure the place is up to code and regulations, a task complicated by Frank buying 400 steaks with his credit card.

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In a plot to get compensation money from the delivery company, the gang conspires to rub chicken feathers all over the steaks to make the meat look contaminated, a mess Charlie must hilariously clean up in order to get Paddy’s Pub a passing grade. The sequence was shot in a continuous ten-minute take, with Rolling stone observing, “On a technical level, it’s a marvel, as well as a creative look at the genuine odd jobs that Charlie does behind the scenes to protect his friends’ livelihoods …”

7 Mac and Dennis Move to the Suburbs

After taking on a bet with Frank and driving Dee crazy as her pseudo-roommates, Mac and Dennis leave the busy streets of Philly for a quieter existence in the suburbs, declaring that they can survive a month living away from the bustling city. It does not take long for the duo to become unnerved by their seemingly dream home, with Mac going mad over the chirping of a low-battery smoke detector and Dennis the noisy pool pump.

Unable to call off the bet because they would then be forced to sleep in the same bed as an old man for a year, the guys are driven to insanity due to the constant monotony of life in suburbia. The most disturbing moment comes when Mac and Dennis sit down for another cheesy noodle dinner, with Mac maniacally revealing to Dennis he switched up the recipe, implying he cooked their recently passed dog and used the meat in the meal.

6 The Gang Goes to the Water Park

The gang heads to the water park for a little summer vacation fun, with Frank and Charlie setting out to go on every ride at the amusement park (including one that has yet to open), Dee and Mac getting pricelessly stuck in a water slide and Dennis finding a 12-year-old protégé and teaching her the tips and tricks of a manipulative sociopath. Dee is amusingly unnerved by the amount of urine in water-park water, and when she gets stuck in a tube ride with Mac, they cause a huge pile-up with kids ramming into them as they come down the slide.

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The comical episode ends with Frank and Charlie attempting to go down the unopened Thunder Gun Express Ride, quickly realizing the importance of water on such attractions that ultimately leads to Frank landing in the pool below spewing blood. At the exact same moment, Dee and Mac are freed from the tunnel and land smack dab in the middle of Frank’s disgustingly funny bloodbath.

5 Misadventures at the Jersey Shore

When Dennis and Dee decide to relive some of their most treasured childhood memories by returning for a vacation at the Jersey Shore, they find that their once idyllic getaway spot has lost its luster and are shocked by its current state. While Mac and Frank set off on inner tubes for a rum ham adventure and Charlie spends some shocking time with the Waitress, Dennis and Dee attempt to reclaim the magic of the Jersey Shore by doing some of their favorite activities.

When they head to the amusement park on the boardwalk and get on a ride, Dee is horrified when her braided hair gets stuck in the gears and Dennis refuses to reach in and pull it out. The epic slow-motion build-up to the ride dropping downward is absolutely hilarious, as Dee panics and shrieks when part of her scalp is ripped off and Dennis vomits after witnessing the whole ordeal.

4 Mac & Dennis: Manhunters

After Dee and Charlie steal and eat the venison Frank went out and hunted, he is told by Mac and Dennis that hunting deer is no challenge and only the greatest are able to hunt a human instead of a vulnerable animal. The two best friends then set out to lure and trap poor ol ‘Rickety Cricket, promising him a date with Dee if he shows up to Paddy’s Pub.

When he inevitably does, Mac and Dennis announce they will be hunting him, and he then runs off; the guys proceed to deck themselves out in camo, hide in a cardboard box on Cricket’s normal route and chug a bunch of beer. The duo amusingly chase after the poor man before deciding a different plan of attack, but the tables are turned when Frank helps Cricket get back at Dennis and Mac by messing with them when they fall asleep through some hilarious shenanigans.


3 Chardee MacDennis

With no plans or schemes in sight, the gang decides to hang around Paddy’s Pub and play a board game, devising their own wonderfully chaotic drinking game they once created known as “Chardee MacDennis.” In the ridiculously wild episode, the three-level game has the gang drinking different alcoholic beverages and participating in zany punishments and challenges, with the whole affair being kicked off with smashing wine glasses and Maori war dances to intimidate the other team.

In Chardee MacDennis, cheating is encouraged, but there are penalties if someone gets caught doing so. Throughout the whole game and episode, everyone becomes more and more aggressive and when they reach Level 3, only hard liquor is served and Charlie, Mac, and Frank berate Dee after she draws an Emotional Battery card. The game showcases just how ruthlessly funny the gang can be, which fans can not get enough of.


2 The DENNIS System

Dennis decides to reveal his foolproof method for seducing women to the gang, which he fondly refers to as the DENNIS System: Demonstrate value, Engage physically, Nurture dependence, Neglect emotionally, Inspire hope, and Separate entirely. While Dee is rightfully appalled by the whole concept, Mac, Charlie and Frank decide to set out and test the system to see if they can win over some women.

It does not take long before things go awry, with Charlie stalking the Waitress and sneaking into her home in an attempt to Demonstrate value, doing so by breaking her garbage disposal so that he can return later to fix it. The guys decide to try and use the DENNIS System on a woman working at the pharmacy, an effort that spectacularly blows up in their faces and causes Dennis to lose his cool on the others for ruining his master plan of seduction.


1 The Nightman Cometh

After a very-cheery Charlie writes a musical, the gang takes on their respective roles solely out of a desire to fuel their own vanity and have their moment in the spotlight. What started out as an honest and well-intentioned endeavor by Charlie soon spirals into a complete disaster, as everyone attempts to capitalize on their temporary “fame.”

Dee is worried her song solo is sending the wrong message about her feelings towards children, as she attempts to ad-lib the lyrics and alter the inappropriately sexual message. Frank is portraying the part of a troll and can not get his lines right either, hilariously altering “You gotta pay the troll toll to get into this boy’s soul” to “boy’s hole,” naturally causing Charlie to go off the deep end over the lyrical flub. The whole stage production is an absolute dumpster fire that has become a beloved staple among Sunny fans, as the chaos and ridiculously funny energy the gang brings is front and center.



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