It's Always Sunny In Philadelphia: Dennis' 10 Funniest Mishaps – Screen Rant

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Dennis Reynolds has been involved in some silly schemes and hilarious mishaps in It’s Always Sunny In Philadelphia. Which are the funniest ones?
As fans continue to eagerly wait for the 16th season of the long-running sitcom, It’s Always Sunny in Philadelphia, some are likely revisiting hilarious previous episodes. The gang is always getting into trouble because of their own actions, with Dennis Reynolds being particularly prone to involving himself in questionable schemes.
His funniest mishaps almost always become meme-worthy iconic moments in the fandom, as they often reveal more about his arrogance and short temper. These misadventures are usually a reflection of Dennis’ strange personality and unique brand of humor.
In one of the most cringeworthy parts of It’s Always Sunny, Dennis and Dee team up to force their way into an exclusive nightclub. Their end goal is to build up their reputation so that they can eventually become celebrities, but that’s predictably far from what happens.
Dennis makes a few new friends at the club who offer to make his nights there more interesting by giving him some mystery pills. Dennis takes too many at some point and ends up starring in an embarrassing commercial the next day. While he did achieve stardom, he’s understandably disappointed to be wearing adult diapers while doing so.
A rare visit to a mental health professional unsurprisingly turns disastrous when the gang insists on making her choose who should wash the dishes. Dennis’ time along with her provides humorous insights about his inflated ego and tendency to be manipulative and controlling.
Instead of acting like her client, Dennis immediately places himself on the same level as the therapist, insisting that they work together and share notes about Dee, Mac, Charlie, and Frank. He even brings out a dossier containing private details about everyone, but the therapist is understandably far from impressed. It’s satisfying to hear her call out Dennis for his bizarre behavior, even though he doesn’t really listen.
When the bar is in need of effective marketing, the owners agree to put up a billboard and host an audition for models. Dennis makes the foolish decision to insult Frank when he suggests he could be the model, which is a choice that will come back to haunt him later.
Dennis jumps through numerous hoops during the audition, getting into a pool full of mud and having detergent thrown in his face. All his efforts turn out to be pointless, though, as Frank soon reveals that he already had the billboard put up with his face instead of a hired model’s. It’s a great example of Frank showing Dennis who’s really in control of Paddy’s funds.
The entire gang gets wedding fever after Mac encounters an old flame. While Charlie and Frank decide to file for a domestic partnership, Dee and Dennis work on their respective own relationships with Bill and Maureen Ponderosa. Dennis is enamored with Maureen, who is clearly still smitten with him as well.
Things move a bit too quickly for the duo, as Dennis and Maureen decide to immediately get married at the courthouse. It soon turns into a headache for Dennis, who slowly realizes that he doesn’t really want to be with her. It’s not as simple to get divorced as it is to get married, however, especially when the Lawyer inserts himself into the situation to make it more difficult for Dennis.
Mac and Dennis have one of the best relationships in IASIP, as their friendship can take some weird turns. One of these happens when they make a bet with Frank, as the two of them claim that they can easily last a month living together in the suburbs.
What follows is the clear deterioration of the friendship, which starts when Dennis takes on the role of the working partner while Mac takes care of the house. Dennis’ situation is particularly gut-busting, as, by the end of it, he’s so close to breaking that a simple polite gesture from his neighbor nearly sends him over the edge. It’s another instance of the character biting off more than he can chew and underestimating his reliance on comfort.
The Reynolds siblings often think they’re superior, with Dennis especially being arrogant about his perceived social status. This aspect of his character is highlighted in a humiliating way when he and Dee attempt to enter an exclusive swim club, claiming that, unlike Mac and Charlie, they can beat the heat in a “dignified” and “upper-class” way.
The duo soon receive a rude awakening about how others truly see them once they’re almost immediately rejected and asked to leave the premises. They soon find themselves enduring the conditions in a chaotic public pool, which is far from what Dennis envisioned for his day off.
Dennis makes one of the funniest mistakes in It’s Always Sunny when he decides to eat a bowl of cereal while waiting for the stoplight. He’s soon rear-ended by a flustered Frank, who claims the accident is Dennis’ fault due to his bad choice of eating cereals on the road.
The situation escalates further than it should, with Dennis’ mishap soon leading to a full-blown fake trial in the bar. His eating habits inspire the classic episode, which shows the chaos and nonsense that fans know and love about the sitcom.
The convoluted “Game of Games” is a legendary competition from the show that has likely inspired similar contests among fans. A memorable part happens during “Level 2,” which features a risky game of darts. Dennis’ hand is placed over the target as Mac and Charlie try to hit it, which they eventually do.
The awkward moment the dart lands right in Dennis’ palm is a highlight of the episode, mostly because he still doesn’t flinch and ends up winning the round. It’s an accident that underscores the great lengths Dennis will go to in order to prove that he’s better than everyone in the room.
In one of the best episodes outside of Paddy’s Pub, the gang goes to the water park and becomes busy with various antics throughout the day. Dennis’ original plan of flirting with strangers is ruined when he meets a young prankster, Abby. They soon bond over their love for scams and stealing.
Dennis seems to genuinely enjoy his time with the mischievous character who soon says a touching farewell. It’s eventually revealed that Dennis got a taste of his own devious medicine, however, as Abby’s true intention was to steal his stuff from the public lockers. It’s a satisfying conclusion that reminds Dennis there are smarter and more devious people out there who can easily fool him.
The most famous mishap Dennis has on the show is centered on his beloved Range Rover, which he tries to sell despite it being half-submerged in the river. Buyers are hesitant to close a deal with Dennis, seeing as how the vehicle obviously won’t function. This continues until Dennis meets someone who’s actually interested in pursuing the sale.
Everything goes well until the potential customer calls it a “starter car,” which enrages Dennis who claims it’s a “finisher car” meant to carry the “golden god.” His ridiculous rant and the entire situation have inspired countless memes and discussions, as it’s a classic moment that sums up Dennis’ volatile personality.
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Saab is an editor and writer for Collider and Screen Rant. Before the two sites, she worked as an editor for a digital marketing company. She's based out of Metro Manila, Philippines, where she lives with her partner, three fat cats, and two hundred houseplants. She's passionate about all things pop culture and design. When she's not typing, she's tending to her indoor garden or watching true crime stories on Netflix.


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