Even by the show’s typical standards, It’s Always Sunny In Philadelphia’s “The Gang Broke Dee” goes dark. When It’s Always Sunny In Philadelphia debuted in 2005, few probably expected it to still be running in 2020. The series revolves around the gang that runs Paddy’s Pub in Philadelphia, who are a motley collection of vain, selfish, prejudiced losers whose many schemes backfire horribly. Despite this, the show is frequently hilarious and has produced classic episodes like “The Nightman Cometh,” “The Gang Solves the Gas Crisis” and “The Gang Makes Lethal Weapon 6.”

Despite frequently broaching controversial issues for dark humor, It’s Always Sunny In Philadelphia works because the joke is almost always on the gang themselves. The series has run for fourteen seasons thus far, with season 15 feeling like something of a safe bet. There was a time fans were concerned about It’s Always Sunny In Philadelphia’s future following the season 12 finale, which made it seems like Dennis had left so Glenn Howerton could work on sitcom A.P. Bio. Those concerns proved unfounded as Howerton still returned for season 13, though Dennis missed a few episodes.

Dee (Kaitlin Olson) is one of the more sympathetic members of the gang in It’s Always Sunny In Philadelphia, since the others relentless mock and bully her. That said, she’s shown time and again to be just as vain, cruel and selfish as they are too. It’s Always Sunny In Philadelphia regularly mines humor from darkness, but season 9’s opening episode “The Gang Broke Dee” really works overtime. It opens with Dee in the bar eating cake that was thrown in the trash while smoking and drinking whiskey. Even the gang’s usual attempts to belittle her fall flat as she beats them to the punchline, sucking out the “fun” of their jokes. She then jokes about jumping in front of a bus, and they realize they’ve finally broken her spirit.

It’s Always Sunny In Philadelphia’s “The Gang Broke Dee” sees them finally rally around her, encouraging her to try stand-up comedy again and use her new broken persona. Her edgy, pitch-black comedy goes over shockingly well with audiences, much to Dennis’ dismay, who focuses on finding her a “below average” man to take her off his hands. As her comedy career ascends, she naturally turns her back on the gang, and Dennis becomes increasingly resentful of her success. A talent agent later offers her a spot on Conan, and despite Dennis’ attempt to jump on the private jet with her to L.A. for the recording, she rejects him.

It’s Always Sunny In Philadelphia “The Gang Broke Dee” makes it appear Dee will spoil this big opportunity by bombing on stage - but it goes even crueler. After being whisked off in a limo and taken backstage, the curtain raises to reveal it was all a massive practical joke by the gang. Everyone from her talent agent to the comedy club crowds were actors, revealing her whole stand-up career was a sham. They wanted to show her its always possible to sink lower and they also reveal Dennis was never in on the gag; Dennis pretends to find this hilarious but is clearly humiliated. Dee ends the episode smashing up the bar while the gang laugh and cheer. It’s Always Sunny In Philadelphia “The Gang Broke Dee” is an example of how well the show understands its characters, and how it can always find new ways to milk humor out of their darkest moments.

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