Let’s face it, as funny as they are, there is basically not one redeemable recurring character on It’s Always Sunny in Philadelphia. They’re always up to something, and it basically never ends well for any of them. The best episodes of It’s Always Sunny revolve around the gang showing their true nature.
Whether that true nature is being a sociopath, manipulative narcissist, or wildcard, it always leads to an entertaining scenario. The important thing to remember is that the gang never learns from their mistakes, and their lives never get better. Here are 10 of the best It’s Always Sunny episodes.
The Gang Gets Whacked Part 1 & 2 (S3 E12-13)
After the gang finds a kilo of cocaine and the mob owners come looking, they’re forced to come up with a scheme to make $25,000 or get whacked. Each member goes their own way, with Dennis getting pimped out by Frank to lonely old women, Mac trying to join the mob but is getting whacked regardless, and Charlie and Dee trying to flip drugs.
This two-part episode has it all. Frank being a pimp, the gang ruining Rickety Cricket’s life even more, Mac inadvertently (or on purpose) making sexually suggestive jokes about men, and Charlie and Dee being drug addicts again.
The D.E.N.N.I.S. System (S5 E10)
Dennis is easily the most abusive member of the cast, constantly using the other members of the gang and side characters to his own benefit. This episode has him teaching the rest of the gang his method for seducing women, which, as you can imagine, is essentially a rollercoaster of gaslighting and emotional abuse.
Dee winds up ruining everything with the one good boyfriend she’ll ever have, Charlie tries to get back with the waitress by paying a carny to stab her, and Mac tries to swoop in on Dennis’s emotionally damaged women with his own system, M.A.C. (Move in After Completion). Frank, meanwhile, is trying to swoop in on top of Mac and Dennis by displaying a wad of hundreds and magnum condoms. Yeah, they get about as depraved as can be in this episode.
Sweet Dee’s Dating a Retarded Person (S3 E9)
While Dee is trying to figure out if her new rapper boyfriend is suffering from a mental disability, the rest of the gang are struggling to agree on what kind of music their new band should play. Frank wants to take a Beatlesesque approach, but Mac thinks they should go punk. Charlie has this whole Bob Dylan thing going on, and the band performs the first song that would go on to spawn a number of memes, callbacks, and jokes for seasons to come, “The Nightman.”
Charlie’s magical talent and ability to turn the trauma of childhood molestation into a song is truly magical, but the guys don’t appreciate it and kick him out. Meanwhile, Dee struggles to understand if her boyfriend is actually mentally disabled. The final performance of Dee’s rapper boyfriend and Charlie and Dennis are both a spectacle you need to watch rather than read about.
The Gang Buys a Boat (S6 E3)
We all want a P-Diddy-style shrimping vessel, right? Well, if not, the gang does, and for $2,500, they got just that. It’s a piece of garbage and needs a lot of work, which Charlie, Dee, and Frank get to while Dennis and Mac go shopping for party supplies.
While they’re out shopping, we get the infamous “the implication” scene that shows how Dennis is an absolute sociopath. Will the gang fix the boat? Will Dennis and Mac get a comfy mattress to help with their “implication”? Or will it all end up in flames like it usually does?
The Gang Gets Analyzed (S8 E5)
The Gang Gets Analyzed really points out everyone’s issues if you didn’t already figure them out for yourself over the last 8 seasons. Dee’s therapist is faced with the task of figuring out who should do the dishes from a friendly dinner they all had but discovers much more lying under the surface.
Mac suffers from body dysmorphia issues and is possibly gay but doesn’t want to admit it. Charlie talks about how he survived an abortion and shares a bed with a man that may or may not be his father. Frank talks about how his skull is like Fort Knox but very quickly unzips and falls apart. Dennis attempts to discuss the others in the group with the therapist as a “colleague.” He also draws a sexual image in an attempt to hit on her. Lastly, Dee shows how horrible an actor she is and how much she needs attention.
If you’re wondering who does the dishes, they smash them.
Chardee MacDennis: The Game of Games (S7 E7)
This episode is great for a multitude of reasons. The episode is extremely creative, yet only takes place inside Paddy’s Pub. The episode relies on the acting and comedy of the cast to make it great since there isn’t much to go off of in the actual scene.
Cheating is not only tolerated but encouraged, and it seems like the gang knows no bounds when it comes to Chardee MacDennis, even driving Dee to suicide at one point in the past. Beyond that, the game itself is extremely hilarious. Dennis’s stone-cold face after taking a dart to the hand and Frank getting put into a dog kennel are all memorable moments.
The Nightman Cometh (S4 E13)
Charlie creates a play and enlists the gang’s help to put it on. The play itself features the Nightman and Dayman from the episode Sweet Dee’s Dating a Retarded Person. Each member of the gang constantly wants to change Charlie’s play or makes mistakes, irritating him to no end.
Dee wants a song she sings changed so it doesn’t sound like she loves little boys. Frank plays a troll that asks for a toll to get the boy’s soul but instead keeps saying it like “boy’s hole.” Mac turns the Nightman into a cat-like karate man. Dennis ends up playing the Dayman, who seems to get raped by the Nightman.
The Gang Gets Held Hostage (S3 E4)
This episode sees the McPoyles return, an incestuous family that hates the gang for a variety of reasons. The McPoyles hold them hostage in the bar and start making demands with the police over the phone. The B plot of this episode sees Frank crawling around in a vent, looking for his will that Charlie hid.
It’s always a joy when the McPoyles appear on screen, and they’re absolute gold in this episode. From Ryan mistakenly stabbing Liam to Liam’s “start breaking bricks wet nips,” this episode is bound to make you laugh.
The Gang Goes on Family Fight (S10 E8)
A great episode that shows each member of the gang’s personality, The Gang Goes on Family Fight also features Keegan-Michael Key. Family Fight is basically Family Feud, and the gang fails horribly at it.
Frank is, well, Frank, and gives answers like “toe knife” to simple questions. Dee can’t help but make sexual double entendres as responses. Mac completely misses the point of the game and has no idea how to play. Charlie guesses random nonsense like “Dragon” when asked, “Things you eat that don’t eat us.” Dennis can’t play the game since he doesn’t think like the common man and constantly gets annoyed at the buzzing noise, finding it irritating and demeaning.
Mac & Dennis Move to the Suburbs (S11 E5)
This episode focuses mostly on Mac and Dennis but is still filled with hilarity. The basic premise is that Mac and Dennis move into a house in the suburbs of Philly, and we follow their attempt to thrive in a new environment. Hint: it does not end well.
Dennis’s reaction to commuting every day to work is extremely relatable, and his constant aggression toward their friendly neighbor Wally is hilarious. Mac’s inability to deal with the beeping smoke detector and feeling like a housewife, along with Dennis’s aggression, culminate in a huge blowout that ends in a dead dog being served with blue box Mac and Cheese.
Wrap Up
We hope you found an episode to watch or rewatch from our list of the best It’s Always Sunny in Philadelphia episodes. It’s impossible to include every good episode of It’s Always Sunny, but we think we nailed the ones that fans can all agree are some of their best work.
Did we miss an episode that you love? Let us know in the comments, and we’ll see if we can fit it into our list! If you’re wondering where the episode with Pepe Silvia is, we covered it extensively over here.
