In time, Deandra “Sweet Dee” Reynolds has become It’s Always Sunny in Philadelphia‘s best character. Kaitlin Olson is never anything short of hysterical and, after the first few seasons, the scripts have matched her comedic energy and desire to be as deplorable as Glenn Howerton’s Dennis, Charlie Day’s Charlie, Rob Mac’s Mac, and Danny DeVito’s Frank. Dee is hungry for fame, but not particularly talented. Like the rest of the Gang, she’s entirely self-absorbed yet can’t seem to understand why she has such difficulty entering meaningful long-term relationships. She dances like an inflatable man in a car lot. She enjoys seeing others suffer and, of course, she’s a bird. That’s Dee, and the following episodes prove why she’s the ultimate scene stealer.
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Olson has been great in so many episodes it was truly difficult to narrow it down to ten. However, we would be remiss to not give a shout out to those that didn’t quite make the cut, 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,” “The Gang Escapes.”
10) “The Gang Broke Dee” (Season 9, Episode 1)
“The Gang Broke Dee” is also almost as much a Dennis episode as it is a Dee episode. And, admittedly, it’s not one of the show’s funnier episodes because it has a tendency to repeat the few gags it has in its arsenal.
However, this one is integral to understanding who Dee is. For years she has convinced herself that she genuinely does have what it takes for her to be an actress. Here she’s manipulated into thinking she has been given that chance and, even with some supposed popularity in her favor, she still gags when the time comes to show her talents off for a national audience. It’s always nice to see a character learn something about themselves.
9) “Charlie and Dee Find Love” (Season 8, Episode 4)
Featuring a pair of excellent guest star performances by Alexandra Daddario and Josh Casaubon, “Charlie and Dee Find Love” is a pretty fantastic take on Dangerous Liasons. Everyone is using some other individual and, in Charlie’s case, he’s actually the most manipulative of them all, which isn’t the standard for him. Dee’s behavior, however, is perfectly in line with her loose, hammered self.
But this episode would make the cut for one simple two-line interchange between Dee and her suitor, Trevor Taft. She’s dancing (horribly and drunkenly) for him and he says “I love how free and uninhibited you are.” With a belch she replies, “Oh yeah? How about I free that big fat snake in your pants and uninhibit myself all over it?” Classic.
8) “The Gang Gets Held Hostage” (Season 3, Episode 4)
“The Gang Gets Held Hostage” is one of the best early days Frank episodes. But even more so it is Dee’s time to shine. As soon as Stockholm syndrome is mentioned, we’re positive that one member of the Gang is going to either convince themselves they’ve developed it or actually develop it.
And we do. Charlie briefly claims to have it, clearly thinking Stockholm syndrome means a traditional fever, but Dee full-on gets it. She sides with their captors, the McPoyle twins and turns their (fake) shotgun on Dennis, Mac, and Charlie. One gets the feeling she didn’t even need Stockholm syndrome to make that choice.
7) “The Gang Buys a Roller Rink” (Season 15, Episode 3)
As it turns out, the name “Sweet Dee” isn’t ironic. There was a time where she actually was, well, sweet. What better time to introduce that fact than a decade and a half into the shows run, when we fans think we know everything there is to know about these characters?
But this revelation isn’t the only thing that makes this episode an all-timer for Dee. There’s also the hilarity of the immediate switch in personality once she bonks her head. Without any delay the vicious personality we’ve come to know and love is on display, and the way Olson delivers the line “Off me, b***h!” to one of her fellow roller-skaters is priceless.
6) “The Gang Solves Global Warming” (Season 14, Episode 7)
Dee is never better than when she’s paired up with Charlie, especially because no one makes her as exasperated as he does. The best example of this is almost certainly Season 14’s “The Gang Solves Global Warming.”
Dee and Charlie go on a little adventure to get a bag of ice, which couldn’t really go any worse. It keeps melting because of the heat wave, so they need to return to the store, at which point the owner has upped the price. All this time Dee is trying to make herself look like an environmentally conscientious citizen on social media. But she isn’t conscientious, she’s Dee, which Charlie then displays to the world. The episode’s high point is when Dee is telling Charlie the next steps of their day. Olson makes Dee display an ultra-controlled, robotic movement that sells her frustration so perfectly it was worthy of an Emmy in and of itself.
5) “The Gang Goes Bowling” (Season 16, Episode 7)
On top of featuring the long-awaited return of the McPoyle brothers, two of Sunny‘s very best supporting characters, “The Gang Goes Bowling” also features Artemis, the Waitress, and Gail the Snail. It’s a reunion tour of an episode.
And yet it’s still all Dee’s. There’s nothing better than seeing Dee confident about something (in this case bowling) only to have someone ruin it, especially when that someone is Dennis, who thrives on seeing her suffer as much as she thrives on seeing enemies like Ingrid Nelson suffer.
4) “Hundred Dollar Baby” (Season 2, Episode 5)
“Hundred Dollar Baby” is an early days Sunny delight. It coasts on a simple pair of premises: revenge and greed. Charlie represents the greed side, though he’s just a tool for Dennis and Mac.
Dee, per usual, represents revenge. Frank has been trying to train her at the gym ever since her “friends” pushed her towards a mugger but, even there, she can’t help but get picked on. Now her rage is directed towards the daughter of Frank’s rival from his younger days, and she’s pushing herself to take on this “prettier” version of herself in the ring. However, Charlie has stolen most of the steroids she’s been scarfing, resulting in two rage-filled individuals butting heads in a way that is unforgettable. They get their respective fights after all, it’s just that neither happens in the ring.
3) “Sweet Dee Gets Audited” (Season 7, Episode 4)
One of Sunny‘s underappreciated masterpieces, “Sweet Dee Gets Audited” is one of the show’s very best comedy of errors. And regardless of whose errors they are, things look especially bad for Dee.
Of course, it’s also Dee’s fault, as she gleefully reveals in the opening scene. She has been scamming the government by claiming the baby she gave up for adoption as a dependent, and now she’s being investigated to see if little “Barnie” is actually hers. This episode has a few top-tier Dee moments. There’s the way she points back to herself while wagging her head in the opening scene, the fact she’s riding a scooter with the license plate “$CAMMIN” when she first meets the auditor, and the entire baby funeral sequence, which she struggles through courtesy of the chili powder Dennis has just blown into her eyes to ensure she cries.
2) “Dee Day” (Season 14, Episode 3)
While it’s not quite as solid as Season 9’s “Mac Day,” “Dee Day” comes mighty close. Unfortunately, unless you buy Season 14 digitally, you can’t see it (and its removal happened not long after it first aired, too).
Like “Mac Day,” “Dee Day” offers a ton of opportunities to really analyze the title character and their interactions with the remainder of the Gang. In the case of Mac, it was his neediness and endless desire to get the attention he perpetually craves. Dee’s way of looking at her day is that it’s an opportunity to torture the hell out of the only four people close to her. Her joy at “tacking on another day” or stripping off Dennis’ makeup is perfectly in-character for her. No one has ever written Dee as well as Sunny EP Megan Ganz, who also scripted “The Gang Escapes,” “Time’s Up for the Gang,” and directed “The Gang Goes Bowling.”
1) “PTSDee” (Season 12, Episode 7)
When Dee hooks up with an exotic dancer, she mistakes his post-coital tears for tears of joy. She does her usual thing of stealing his watch so he’ll come back to her at which point he reveals that he was crying because she represented his rock bottom. He gets drunk all day, dances for women he doesn’t care about and who don’t care about him and hooks up with random women for one-night stands. All throughout this revelation, Dee’s eyes just grow wider and wider and her face becomes a stone.
Dee tells Charlie and Dennis that she’s no rock bottom…she’s a rock. She makes men better. And throughout the episode we think she actually is making an effort to do so with this man. She gets him paid for playing videogames with Frank, goes along with him to a PTSD meeting (even though the man just dances as a soldier, he’s not an actual veteran), and seems to be acting supportive. However, when she gets him a gig dancing at Paddy’s, all is revealed. She had been scheming all along, with her ultimate goal being to get the exotic dancer to strip in a poorly lit room for his estranged daughter. And as soon as his genitals are in his daughter’s face, Dee turns on the lights and cackles as her one-night stand runs out of the bar in an embarrassed panic. The darkest thing Dee has ever done, which also makes it the most Dee thing Dee has ever done.
