It’s Always Sunny In Philadelphia: 10 Best Dee Episodes

It’s Always Sunny in Philadelphia would not be the same without Dee Reynolds. Here are the bird’s best episodes.

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As Paddy’s resident bartender (and bird), Sweet Dee is a core member of It’s Always Sunny in Philadelphia’s iconic Gang. She has been around since season one, and Kaitlin Olson has proven herself to be an absolutely brilliant comedy actress. Dee is prone to violent outbursts, proudly mean-spirited, and unflinchingly egotistical while simultaneously lacking any self-worth.

Dee is treated especially horribly by the rest of The Gang, which is saying something considering each one of them is willing to sell out anyone else for a beer and a box of Tic Tac. While Dee is always good for a laugh, she tends to be overshadowed by the other members of The Gang, even in episodes where she drives the main plot forward such as “Dee Reynolds: Shaping America’s Youth.” That said, there are still quite a few episodes that highlight the complex enigma that is Dee Reynolds.

10 Sweet Dee Has a Heart Attack

While Mac and Charlie’s conspiracy-laden mailroom gig is unquestionably the highlight of “Sweet Dee Has a Heart Attack,” the titular character still gets her share of memorable moments.

By season 4, it had become crystal clear that The Gang cared very little about Dee. This episode illustrates that splendidly when the guys react with mild annoyance at the latter having a heart attack. This event leads to Dennis and Dee trying to become healthier, although things do not quite work out.

9 Who Got Dee Pregnant?

Dee rarely gets one over on the guys, but “Who Got Dee Pregnant?” is (almost) an exception. When Dee decides to pop out a baby to make a bit of cash, she decides to trick The Gang into believing one of them is the father. In order to figure things out, the guys try to remember what happened during a Halloween party.

Amusingly enough, Dee’s funniest scene in the episode involves her being literally replaced by a bird.

8 The Gang Dines Out

When The Gang inadvertently end up at the same restaurant, Dennis (and Mac) and Frank (and Charlie) engage in a battle of egos to see who will be the first to pay tribute to the other table. Dee is also at the restaurant, but she cannot seem to find any way for her to be noticed by the other characters.

This is Dee at her most attention-seeking and pathetic, two traits she wears extremely well. The ending is also one of the more positive ones for Dee, as her actions bring everyone together.

7 Dee Day

Despite failing to reach the same heights as “Mac Day,” season 14’s “Dee day” is nevertheless a memorable episode that acts as a celebration of Deandra’s worst (and funniest) eccentricities. Naturally, this includes forcing the guys to act in a wildly inappropriate stage show that calls back to some of Dee’s racist caricatures of past episodes.

Dee even gets the last laugh at the end of the storyline by tricking the guys into participating in a second Dee Day.

6 PTSDee

Out of all the main characters, Dee is the least self-aware. While she has wrecked her fair share of lives over the years, Deandra still tries to take the moral high ground whenever possible. Unsurprisingly, these moments tend to feel unearned.

In “PTSDee,” Dee weaponizes self-denial to shield herself from the knowledge that she is considered to be a male stripper’s rock bottom. In an attempt to prove him wrong, Dee demonstrates that she is actually far worse than he ever imagined.

5 Dennis And Dee Go On Welfare

Season 2’s “Dennis and Dee Go on Welfare” is It’s Always Sunny in Philadelphia’s first great episode. This entry gives each character an opportunity to shine, but the titular siblings are especially brilliant.

Back then, Dee and Dennis were often on the same side, a partnership that extended to going on welfare and picking up an addiction to crack cocaine. Dee makes for a hilarious crackhead, with Olson delivering a performance that is both hilarious and realistic.

4 The Waitress Is Getting Married

As seen in episodes such as “The Aluminum Monster vs. Fatty Magoo,” Dee’s ego is so fragile that the mere thought of someone else succeeding is enough to drive her crazy. “The Waitress Is Getting Married” uses Sweet Dee’s insecurities to craft a comedy masterpiece.

When Deandra learns that the Waitress is engaged, she sets out to ruin the wedding by seducing the latter’s fiance, who happens to be Dee’s high school boyfriend. Dee embarrassing herself for selfish reasons is always a recipe for success.

3 The Gang Gets Whacked: Part 2

Even if she refuses to acknowledge it, Dee has ruined Rickety Cricket’s life by taking advantage of the latter’s feelings for her. “The Gang Exploits A Miracle” established this dynamic but “The Gang Gets Whacked: Part 2” was the episode that made the most of it.

Over the course of a few days, Dee turns Rickety Cricket into a drug dealer and a crack addict, a process that highlights the former’s propensity for pure evil acts. Dee at her worst is Dee at her best.

2 Hundred Dollar Baby

A parody of Fight Club and Million Dollar Baby, “Hundred Dollar Baby” lets Dee go completely off the rails as she tries to pick up some self-defense tips. It is amazing to behold and presents a version of the character that is a touch more forceful than usual.

With Frank serving as her trainer, Dee turns to steroids in order to win a boxing match against a far more experienced fighter. While that match never takes place, Dee does get into a memorable scuffle with Charlie.

1 The Gang Broke Dee

The guys might argue over everything and anything, but the one thing that brings them together is their shared love for mocking Dee. Season 9’s “The Gang Broke Dee” felt like an episode that was years in the making, as it paid off Deandra’s deteriorating mental health while also tapping into the character’s aspirations for superstardom.

The punchline – that Dee’s sudden brush with fame was entirely orchestrated by The Gang –ranks among the show’s best.

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