It’s Always Sunny In Philadelphia definitely has an interesting cast of characters that individually each have very unique personalities. But perhaps the most unique of them all is Dennis Reynolds. Dennis is co-owner of Paddy’s Pub, along with Mac and Charlie, and Dee, his twin sister, also works there. But Dennis is the alpha of them all and makes sure they know it time and time again. His domineering personality can be a lot to take in. He’s also known for being manipulative, emotionless, egotistical, and quite honestly, sociopathic.
Regardless, we can’t help but laugh at all of the insane antics he gets up to either by himself or with the rest of the gang. It’s Always Sunny has been on 14 seasons, so while it wasn’t easy, we managed to narrow down our top 10 favorite Dennis episodes of all-time. Let’s see if yours made the cut.
The Gang Gets Analyzed
Like most It’s Always Sunny episodes, “The Gang Gets Analyzed” starts off with a nonsensical storyline that only gets crazier as the episode goes on. Dee goes to her therapist to discuss what went wrong with the dinner she planned with her friends to discuss her problems with them. The issue that made the dinner completely unravel? No one was assigned the dishes.
This led to each member of the gang being individually analyzed by Dee’s therapist. But it’s Dennis who believes he can help everyone else with their problems. He acts as though he’s a therapist himself, even though he’s been manipulating Mac into taking diet pills and has also been keeping files on all of his friends for decades. The way he acts as though it’s everyone else who is crazy is what makes this episode truly hilarious.
Mac And Dennis Break Up
This entire episode centers on what happens when Mac and Dennis decide to take a break on their friendship after Dee tells them they’re too close. It literally affects every member of the gang in different negative ways.
On Dennis’ end, he’s the one who decides to initiate the break up with his best friend and roommate. But it’s clear he’s soon regretting it because he doesn’t have Mac there to take care of his every need, like peeling the skin off an apple. He also doesn’t have his best buddy to watch the same action movie with over and over again which bugs the hell out of him. His reactions to all of these “problems” are what made the episode an instant classic.
The Gang Group Dates
Out of all of Dennis’s best episodes, this one is likely the most quotable of them all. Any Sunny fan will tell you that Dennis Reynolds is a “five-star man” and it’s all because of this episode right here.
The gang decides to try their hand at using dating apps while simultaneously using their bar as the meeting location for local singles to get more business. Unfortunately for Dennis, he becomes more obsessed with being “rated” by his dates in a negative way than focusing on the dates themselves. This results in him constantly screaming he’s a “five-star man” as women are more and more put off by his behavior.
Old Lady House: A Situation Comedy
When Charlie thinks Mac’s mom is holding his mom hostage at their home, the gang decides to install nanny cams to spy on them to see what is actually going on.
But it’s Dennis who turns the entire situation into a sitcom for his own viewing. As they watch Charlie’s mom nearly hit Mac’s mom in the head with a hammer, it goes from dark to hilarious with Dennis just adding a laugh track to the moment. The way Dennis managed to take their predicament and turn it into a hysterical comedy easily made this one of his best episodes to date.
The Gang Gets Quarantined
With a deadly flu taking over Philadelphia and the Boyz II Men concert coming up for the gang, they all decide to quarantine themselves at Paddy’s until they can go to the concert. Frank is more concerned about dying from the flu, so when the rest of the gang doesn’t follow the rules, he ends up locking them in the bathroom, one by one.
Dennis is the first to end up in there and he quickly looks like he might die from the flu. Even so, he’s still more focused on singing for Boyz II Men and acting as though he’s fine. Watching him deteriorate as he still tries to convince everyone he’s in perfect health is what makes this one of our favorites.
The Gang Dines Out
Dennis and Mac have a monthly dinner at the local Italian restaurant but in this episode, Charlie and Frank also show up to celebrate an anniversary. Dee is there by herself, as well, but no one notices. Instead, the two sets of men compete all night so the other group will pay tribute to them. Of course, that never happens, and chaos ensues because of it.
But it’s Dennis who is the true standout. He can’t focus on his dinner because he’s obsessing over his horrible chair, the fact they’re seated near the kitchen and that Frank and Charlie won’t pay tribute. It’s classic Dennis and we love it.
Mac & Dennis Move To The Suburbs
Dennis and Mac get an idea in their head that they’d prefer the suburbs over the city life because of cheaper rent and open spaces, but they soon learn just how wrong they were. Dennis is a frazzled, irritated, and stressed out mess the entire time. He’s constantly annoyed with Mac, who is just leading a life as a stay at home husband at this point.
Watching Dennis slowly but surely losing his mind all because they live in the suburbs is easily the most hilarious part of the episode.
The Gang Buys A Boat
Two words: the implication. This conversation Dennis has with Mac during this episode is easily one of the most iconic Dennis scenes of the entire series. But let’s start at the beginning. Dennis, Mac, and Charlie decide to purchase a new boat after coming into money. Though it’s not much, they still expect an amazing boat, but end up with a vessel that would’ve been better off left at sea.
While they try to spruce it up, Mac and Dennis are at the boat store where Dennis explains what “the implication” of being out on a boat with a strange man is for young women. It’s equal parts terrifying and hilarious.
The Gang Gets Trapped
It’s the Indiana Jones and It’s Always Sunny crossover we never knew we needed. Inspired by the classic film, the gang breaks into a house to steal a vase that they believe belongs in a museum.
In actuality, the family had bought the vase at an auction fair and square, so the museum really had no claim on it. But while they’re in the house to steal it back, they get trapped when they realize the homeowner is actually home. This leads to a chaotic turn of events that is pretty typical for the gang, but Dennis steals the show with his phobia of people from the south and the fact he was the only voice of reason for most of the episode.
The D.E.N.N.I.S. System
And now we have the most iconic Dennis Reynolds-focused episode in It’s Always Sunny In Philadelphia history. The entire episode is about Dennis and his fool-proof plan to seduce women. He believes with this plan, that no matter what, he can always get these women back, even after he has left them in the dust.
This sets off a series of events with the rest of the gang either trying and failing to use the system themselves, or in Dee’s case, trying to avoid having the system used on her by her boyfriend. The way Dennis breaks down his system is the best part of the whole episode and is a favorite of Sunny fans everywhere.
