The 10 Best Sweet Dee Episodes of It’s Always Sunny in Philadelphia

Over time, Deandra “Sweet Dee” Reynolds has become the standout character in It’s Always Sunny in Philadelphia. Kaitlin Olson is consistently hilarious, and thankfully, the writing has evolved to match her incredible comedic timing and willingness to be as awful as the other members of the Gang – Glenn Howerton’s Dennis, Charlie Day’s Charlie, Rob McElhenney’s Mac, and Danny DeVito’s Frank. Dee desperately wants to be famous, but she lacks genuine talent. Like the rest of the group, she’s completely focused on herself, yet she doesn’t realize why she struggles to form lasting, meaningful relationships. Her dancing is famously awkward, resembling an inflatable tube man. She gets pleasure from the misfortune of others, and, famously, she believes she’s a bird. That’s Dee, and the following episodes demonstrate exactly why she consistently steals the show.

It was really tough to pick just ten episodes because Olson has been fantastic in so many! We also want to acknowledge some great episodes that didn’t quite make our top ten, including “The Gang Gets Analyzed,” “Time’s Up for the Gang,” “The Gang Spies Like U.S.,” “Dee Gives Birth,” “Dee Reynolds: Shaping America’s Youth,” “The Gang Replaces Dee with a Monkey,” and “The Gang Escapes.”

10) “The Gang Broke Dee” (Season 9, Episode 1)

“The Gang Broke Dee” feels like an episode focused on Dennis just as much as it is on Dee. And, to be honest, it’s not one of the show’s most hilarious installments, mainly because it relies on repeating the same jokes and gags quite a bit.

However, this aspect is key to understanding Dee’s character. She’s spent years believing she has the potential to be an actress. In this situation, she’s led to believe she’s finally getting that opportunity, and even with a bit of apparent public support, she still struggles with performing her talents on a national stage. It’s always rewarding to see a character gain self-awareness.

9) “Charlie and Dee Find Love” (Season 8, Episode 4)

“Charlie and Dee Find Love” is a really strong episode, especially with great appearances by guest stars Alexandra Daddario and Josh Casaubon. It’s a clever spin on the story of Dangerous Liasons, where everyone is trying to use someone else. Interestingly, Charlie is the one doing most of the manipulating, which is unusual for his character. Dee, though, acts exactly as you’d expect – wild and reckless.

Honestly, this moment is absolutely one of my favorites. It’s a quick little exchange between Dee and her, shall we say, *enthusiastic* admirer, Trevor Taft. She’s attempting to dance for him – and failing spectacularly, fueled by a bit too much to drink – and he tries to be complimentary, saying “I love how free and uninhibited you are.” But Dee, never one to miss a beat, responds with a belch and then drops this line: “Oh yeah? How about I free that big fat snake in your pants and uninhibit myself all over it?” It’s just classic. Seriously, that delivery is perfection! It’s a moment I’ll always remember and totally hilarious.

8) “The Gang Gets Held Hostage” (Season 3, Episode 4)

“The Gang Gets Held Hostage” is a standout episode from the earlier seasons of It’s Always Sunny in Philadelphia. However, it really gives Dee a chance to be the center of attention. The moment Stockholm syndrome is brought up, you just know that one of the Gang members will either pretend to have it, or genuinely start to believe they do.

And that happens. Charlie quickly mentions he has it, mistakenly believing Stockholm syndrome is a regular fever, but Dee genuinely understands it. She sides with those holding them captive-the McPoyle twins-and points their (pretend) shotgun at Dennis, Mac, and Charlie. You get the sense she would have made that choice even without Stockholm syndrome influencing her.

7) “The Gang Buys a Roller Rink” (Season 15, Episode 3)

Interestingly, the nickname “Sweet Dee” isn’t actually sarcastic. There was a period when she genuinely was sweet. What’s a more surprising time to reveal this than after fifteen years of the show, when fans believe they already understand everything about these characters?

However, this discovery isn’t the sole reason this episode is considered one of the best for Dee. The humor stemming from her immediate personality change after hitting her head is also a major highlight. Without missing a beat, the fierce personality we’ve grown to enjoy is apparent, and Olson’s delivery of the line “Off me, bh!” to another roller-skater is truly priceless.

6) “The Gang Solves Global Warming” (Season 14, Episode 7)

Dee truly shines when she interacts with Charlie, even though he often frustrates her more than anyone else. A perfect illustration of this dynamic is likely the episode “The Gang Solves Global Warming” from Season 14.

Dee and Charlie embark on a simple trip to buy a bag of ice, but everything goes wrong. The ice keeps melting due to a heat wave, forcing them to return to the store, only to find the price has increased. Throughout this ordeal, Dee attempts to portray herself as an environmentally aware person on social media. However, she’s not genuinely concerned; she’s Dee, and Charlie exposes this to everyone. A standout moment of the episode occurs when Dee is explaining their plans to Charlie. The director, Olson, has Dee perform a very stiff, robotic movement that perfectly conveys her frustration – it was so well done, it deserved an Emmy award on its own.

5) “The Gang Goes Bowling” (Season 16, Episode 7)

Beyond bringing back the long-awaited McPoyle brothers – two of Sunny‘s most memorable supporting characters – “The Gang Goes Bowling” also includes appearances by Artemis, the Waitress, and Gail the Snail. It feels like a special reunion episode.

But honestly, it always comes back to Dee, doesn’t it? There’s just something so satisfying about watching her genuinely feel good about herself – like when she’s bowling well – only for someone to come along and mess it up. And it’s *especially* good (or bad, for Dee!) when that someone is Dennis. He really gets a kick out of seeing her miserable, which is ironic considering how much *she* enjoys watching people like Ingrid Nelson fail. It’s a whole cycle, really.

4) “Hundred Dollar Baby” (Season 2, Episode 5)

“Hundred Dollar Baby” is one of the first truly funny Sunny episodes. It’s built around two straightforward ideas: getting revenge and being greedy. Charlie embodies the greed, but he’s mostly being used by Dennis and Mac.

Dee, as always, is focused on getting revenge. Frank has been trying to help her train at the gym ever since her so-called “friends” led her into a dangerous situation with a mugger, but she still finds herself being targeted. Now, she’s directing her anger towards the daughter of an old rival of Frank’s, and she’s determined to fight this “prettier” girl in the ring. Unfortunately, Charlie has taken most of her steroids, which means there are now two incredibly angry women about to clash in a truly memorable way. They both end up in fights, but surprisingly, neither of them takes place inside the ring.

3) “Sweet Dee Gets Audited” (Season 7, Episode 4)

As a huge fan of Sunny, I think “Sweet Dee Gets Audited” is seriously one of their most brilliant, yet somehow overlooked, episodes. It’s a classic comedy of errors, and honestly, things get *really* rough for Dee. No matter who messes up, she’s the one who ends up in a terrible situation!

Certainly, Dee also plays a role, which she happily admits right away. She’s been fraudulently claiming her adopted child as a dependent on government assistance, and now she’s under investigation to determine if little “Barnie” is actually her biological child. This episode features several standout moments from Dee. There’s her gesture of pointing to herself while shaking her head in the opening scene, the fact that she’s riding a scooter with the license plate “$CAMMIN” when she first encounters the auditor, and the whole baby funeral scene, which she awkwardly gets through thanks to Dennis blowing chili powder into her eyes to make her cry.

2) “Dee Day” (Season 14, Episode 3)

Though not *quite* as iconic as the “Mac Day” episode from Season 9, “Dee Day” is a very strong contender. Sadly, if you didn’t purchase Season 14 digitally, you won’t be able to watch it-and it was taken down soon after its initial release, too.

Similar to “Mac Day,” “Dee Day” provides many chances to closely examine the main character and how she interacts with the rest of the Gang. With Mac, the focus was on his dependence and constant need for attention. Dee, however, sees her day as a chance to relentlessly bother the only four people she cares about. Her happiness from “adding another day” or removing Dennis’ makeup is completely consistent with her personality. No one has portrayed Dee as skillfully as Sunny EP Megan Ganz, who also wrote “The Gang Escapes,” “Time’s Up for the Gang,” and directed “The Gang Goes Bowling.”

1) “PTSDee” (Season 12, Episode 7)

When Dee sleeps with a dancer, she wrongly assumes his tears afterward are happy ones. True to form, she steals his watch, hoping he’ll return, but he then confesses she symbolizes his lowest point. He spends the day drinking, performing for women he’s indifferent to, and having meaningless one-night stands. Throughout this confession, Dee’s eyes widen in shock and her expression becomes completely blank.

Dee insists she isn’t at her lowest point-she is the foundation. She claims she improves men, and for much of the episode, it seems like she’s genuinely trying to help this particular guy. She arranges for him to get paid to play video games with Frank, accompanies him to a PTSD meeting (though he just performs a soldier dance and isn’t a veteran), and generally appears supportive. However, when she books him a dancing gig at Paddy’s, her true intentions come to light. She’s been manipulating him all along, ultimately aiming to have him perform an exotic dance in a dimly lit room for his estranged daughter. The moment his genitals are visible to his daughter, Dee flips on the lights and laughs maniacally as her one-night stand flees the bar, mortified. This is arguably the most appalling-and yet, most characteristically Dee-thing she’s ever done.

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2025-10-05 02:14