The Best ‘It’s Always Sunny in Philadelphia’ Episodes for Each Member of the Gang

Deandra ‘Dee’ Reynolds

Episode: “The Gang Goes Bowling,” Season 16 Episode 7

Why It’s Her Best: The gang discovers that Dee’s in a bowling league and decides to join it as they really have nothing better to do. And so, a battle of the sexes begins as Dennis, Charlie, Mac and Frank go toe-knife-to-toe-knife with Dee’s team. 

Yes, it’s a newer episode, but it ranks as Dee’s high point as it finally reveals an actual hidden talent (bowling) while having her helm her own version of the gang consisting of Artemis, The Waitress and the consistently dreadful Gail the Snail. We see Dee triumphantly soar (like a bird) as she finally overcomes Dennis’ mind games and, after an endless string of gutterballs, knocks down a single pin to seal the victory. It’s a rare taste of success for Sweet Dee against the gang’s bullying that hits harder due to the decade-plus of buildup.

Ronald ‘Mac’ MacDonald

Episode: “Charlie Wants an Abortion,” Season 1 Episode 2

Why It’s His Best: When Charlie is approached by a woman he previously slept with, he learns that he has an illegitimate son, sparking an abortion debate within the gang. During an abortion rally, Mac and Dennis determine where they stand on the issue based on the hotness level of the women on each side. This early episode is Mac’s strongest as his hypocritical, selfish and degenerate nature helped shape and define the show’s wild sense of humor. It also served as an early example of no topic being “off-limits,” while introducing Mac’s unique brand of religious zealotry — a character constant, whether in or out of the closet.  

Dennis Reynolds

Episode: “The D.E.N.N.I.S. System,” Season 5, Episode 10 

Why It’s His Best: After a woman leaves Dennis a screaming voicemail, he explains to the gang that she’s simply in love with him, before breaking down his deranged seduction process. He walks them through each horrifyingly manipulative tactic in his arsenal to get women to drop their guard, including faux emotional connections, fictional stalkers and fake heroism to increase his perceived value. It’s the purest distillation of the character, helping define the comedically psychopathic human that is Dennis Reynolds.

Frank Reynolds

Episode: “Who Pooped the Bed?,” Season 4, Episode 7

Why It’s His Best: After a series of planted poops pop up in Charlie and Frank’s life, the gang rallies together with Artemis to solve the case of the anonymous turds and track down the evil pooper. During the investigation, there are several accusations and infighting as everyone is at each other’s throats to find the crapping culprit. The hilarious reveal that Frank is behind all of the poops perfectly sums up who he is (“Because poop is funny!”), while also providing a hall-of-fame ending. 

Charlie Kelly

Episode: “The Nightman Cometh,” Season 4, Episode 13

Why It’s His Best: Charlie emerges from the back office revealing to the rest of the gang that he has composed an entire musical about his made-up character “Nightman.” True to their attention-craving nature, the gang agrees to be in the cast as Charlie sets out to make his vision come to life via a local theater. After an absolute trainwreck of a production, Charlie declares his love for The Waitress with a musical proposal as “Day Man” and is promptly rejected. 

“The Nightman Cometh” exhibits all the things that make our favorite illiterate the weirdly hilarious character he is. It’s also the biggest showcase of Charlie’s remarkable creative talents as he completes a massive musical, which is still sung by Sunny fans to this day.