Before these words are written about It’s Always Sunny in Philadelphia‘s long suffering butt of every joke, Deandra ‘Sweet Dee’ Reynolds, it must be noted that she’s a bird. No two ways about it, she’s Paddy’s Pub’s bird, but still a bird. But she’s an interesting bird, not exactly likable but more often than not more likable than her peers. That is until later in the series when, not unlike her ‘father’ Frank, she deteriorates in stature and respectability…fast. These are the best episodes for Dee fans, and thanks to the perpetual power of Kaitlin Olson’s unforgettable performances, there are even more.
20 “The Gang Gets Invincible” (Season 3, Ep 2)
“The Gang Gets Invincible” is as direct a movie reference as Sunny is capable of throwing at the audience. Or, rather, willing.
Dennis, Mac, Dee, Frank, and Charlie leave the bar for once and go to a public park. There, they learn from some men practicing that the Eagles are holding open tryouts in an effort to emulate the success of the Mark Wahlberg-led Disney film Invincible. Frank and Charlie sit the opportunity out, but Mac, Dennis, and Dee (with a fake mustache and beard) dive in. Even with the fuel of pure arrogance, Mac and, especially, Dennis, fail. But Dee goes pretty far…right up until she breaks her foot on a demonstrative kick-off.
19 “The Aluminum Monster vs. Fatty Magoo” (Season 3, Ep 5)
A notable episode for several reasons, “The Aluminum Monster vs. Fatty Magoo” is a standout episode for two characters: Dennis and Dee. For Dennis, it’s one of the first in-depth examinations of his vanity, which would grow in intensity until it becomes full-on sociopathic behavior.
On Dee’s end, there’s her propensity for jealousy and wrath (the latter of which would have a major part in Season 11’s finale The Gang Goes to Hell). The target of her jealousy is Ingrid Nelson, played by Judy Greer, who came back in Season 7 but needs to come back once more.
18 “Frank Sets Sweet Dee on Fire” (Season 3, Ep 8)
Back in Sunny‘s cheaper days, the impact of the series was buoyed by both its Standard Definition look and the small nature of its A- and B-plots. Dee gets to be involved in both plots of “Frank Sets Sweet Dee on Fire,” and she’s by far the heart of the episode.
The A-plot has Frank, Mac, and Charlie attempting to make a public access news show (which Dee and Dennis scoff at). This naturally devolves to them trying to frame a story where Dee enters a building to save some cats. And, of course, that building is filled with gasoline. The B-plot is a little stronger, both for Dee and in general, with her and Dennis trying to make it big on the vain club scene…which ends up getting them on the very public access station they earlier disparaged.
17 “America’s Next Top Paddy’s Billboard Model Contest” (Season 4, Ep 3)
While it’s one of It’s Always Sunny‘s most controversial episodes, having since been pulled from Hulu, “America’s Next Top Paddy’s Billboard Model Contest” is a riot. There’s much to be said or written about content being pulled for the sake of censorship but suffice it to say it’s unfortunate some hilarious episodes of not just Sunny but shows like 30 Rock have been practically banned given the DVD market’s increasing lack of relevance.
And it’s for Dee’s plot line that the episode has been yanked from streaming. Admittedly, her use of blackface isn’t funny, but in that lies the point. The residents of Philly don’t find it funny, the audience doesn’t find it funny (at least they’re not supposed to)…not even Dee’s brother, father, and friends find it funny. But Dee does, which is perfectly in character, and that’s the heart of the episode. Not to mention, it’s pretty darn funny to see Charlie pelt a dodgeball at her face while she’s trying extra hard to look dignified.
16 “Dennis Reynolds: An Erotic Life” (Season 4, Ep 9)
When Dee starts gagging out of panic, she’s Always Sunny‘s funniest character, and “Dennis Reynolds: An Erotic Life” was the first (it even lets Charlie get in on the gagging). The B-plot of Dennis Reynolds: An Erotic Life is actually stronger than the A, mostly because the pairing of Dee and Charlie is one of the series’ strongest.
And there’s a simplistic charm to them trying out life in one another’s shoes for a day. From their failed stand-up set to Dee scarfing down cat food just so she can fall asleep, their plot is a joy.
15 “The Gang Exploits the Mortgage Crisis” (Season 5, Ep 1)
While Dee was initially the Gang’s sane, well-put-together member, time has shown her to be every bit the schemer that Dennis, Charlie, Mac, and Frank are. For instance, “The Gang Exploits the Mortgage Crisis,” which has Dee try to become a surrogate mother.
That in and of itself isn’t a scheme, but it would become one in Season 6. In other words, The Gang Exploits the Mortgage Crisis is an important episode in showing Dee’s development (not to mention her attempt at a double jack knife off a diving board).
14 “The Waitress Is Getting Married” (Season 5, Ep 5)
“The Waitress Is Getting Married” is Dee-fueled cringe humor at its best. She’s never been more pathetic, from hosting a wedding shower that’s clearly geared towards her stealing away the groom to holding up traffic just to invite the duo to the aforementioned gathering, she seems to have no limits.
But Dee does ellicit quite a bit of empathy from the viewer throughout the episode. She’s pretty mean to just about everyone in her general vicinity on a daily basis, but it’s not as if the people she’s more or less forced to spend time with are sterling examples of kindness. If she were to find love and get married, maybe she’d go back to earning her nickname.
13 “Who Got Dee Pregnant?” (Season 6, Ep 7)
Told in flashback, “Who Got Dee Pregnant?” is one of Sunny‘s most compelling episodes. And, true to form, the mystery at the episode’s core is nothing more than a lie to get some sympathy and attention.
Kaitlin Olson’s various readings of the line I’ve got milk all over me!’ are pretty darn funny, but the episode’s highlight must be when Dee is supplanted with a live ostrich in Mac’s memory. If the viewers ever had any question as to whether the Gang actually sees Dee as a lanky, flightless bird, “Who Got Dee Pregnant?” answers it.
12 “Sweet Dee Gets Audited” (Season 7, Ep 4)
When Dee attracts the attention of the IRS, Paddy’s Pub and Frank’s shell companies suddenly run the risk of shared spotlight. The scheming at play in “Sweet Dee Gets Audited” is inspiring in its desperation, but even more so in its depravity, with the Gang ultimately putting a rotted dead dog in a casket intended for a baby.
Dee’s frantic evasion of the IRS agent is hysterical, as is her beaded sweat when the agent catches up to her. Things don’t get much better for her, and Dennis ‘helps’ by blowing chili powder in her eyes to elicit tears. It elicits blood instead. The key to comedy is frustration and struggle, and Deandra Reynolds suffers a lot of both when she Gets Audited. So much for beating the system.
11 “Charlie and Dee Find Love” (Season 8, Ep 4)
Kaitlin Olson has found great success outside of Sunny, and it couldn’t be further from surprising considering how much range she shows in the episode’s opening scene alone. The way that Dee bursts out of her car, with a bat already in hand and expletives spewing only to stop cold at seeing Trevor Taft’s handsomeness is unforgettable. The predictable dry heaving sounds that follow? Even more so.
“Charlie and Dee Find Love” is a bit more on Charlie’s side of the coin, but Dee certainly gets her fair share of moments. The standout is her drunken, stumbling attempt at sexy dancing for Trevor, topped off with the line ‘How about I free that big fat snake in your pants and uninhibit myself all over it?’
10 “The Gang Gets Analyzed” (Season 8, Ep 5)
Kerri Kenney-Silver was a great addition to the Gang’s dynamic in Season 8’s “The Gang Gets Analyzed.” Not only one of the season’s funniest episodes but easily the most important for the characters’ development, it’s an important episode for the entire quintet, and it’s all because Dee dragged them to therapy.
The fact that the inciting incident is a stack of unwashed dishes is both fully in line with the Gang’s personalities and hilariously perfect. The same could be said of the Gang and their learning absolutely nothing about themselves. That is, nothing they’ll expend any effort to improve. That’s a safe prediction, just as is Dee’s therapist never allowing another appointment after her client smashes the aforementioned stack of dirty dishes on her office floor, one by one.
9 “The Gang Group Dates” (Season 10, Ep 2)
If any member of the Gang is hysterical when arrogant, it’s Dee. Olson’s reading of the line ‘Looks like this spider just cost herself a fly’ in the accent of a Southern Belle is proof enough.
“The Gang Group Dates” has the five learning the true level of their appeal in the dating world. For Dennis, it’s a rude awakening. But it’s not much better for his sister, who learns that she’s basically just garnered a reputation for being easy, not for having any sort of discernible power she so obviously craves. Even still, there’s no more fun a human being to see get in their own head than ‘Sweet Dee.’
8 “Dee Made a Smut Film” (Season 11, Ep 4)
While Charlie Day’s emulation of Richard Grieco’s cool guy persona is some of the actors best work in Sunny Season 11, “Dee Made a Smut Film” really belongs to Dennis, Dee, and Frank. On Dennis’ side of things, the audience learns that he experienced trauma in his earlier years, not unlike Charlie. On Frank’s side, there’s a flamboyant character (Ongo Gablogian) that allows Danny DeVito to have some extra fun.
But “Dee Made a Smut Film” is, of course, really Dee’s. The character has a surprising amount of agency in the episode, and she’s shown (slightly) more respect than usual by her peers. Dennis goes to her as a last resort to bring his memoirs to cinematic life, but he does still go to her. It’s not a surplus of respect directed towards the character, but a nice little departure nonetheless.
7 “The Gang Goes to Hell” (Season 11, Ep 9)
Dee just can’t control her wrath. Season 11’s two-part finale, “The Gang Goes to Hell,” has Mac dragging his peers onto a Christian cruise. While on that cruise, he’ll learn much about himself, but the rest learn something too: They’re legitimately incapable of change.
Each member of the gang gets one of the Seven Deadly Sins attached to them. Frank and Charlie are gluttony, Dennis is lust, and Dee gets wrath. Dennis gets a solid creepy moment and Charlie and Frank drink boat fuel, but it’s Dee who stands out. Her crass interactions with a fellow boat passenger (who turns out to be a magician) are hysterical, especially given the ease with which Dee unloads hardcore expletives on a complete stranger while in the middle of the ocean on a vessel specifically geared towards kind-hearted Christians.
6 “The Gang Goes to a Water Park” (Season 12, Ep 2)
Each season of It’s Always Sunny in Philadelphia is memorable for one reason or another, and in the case of Season 12 at least one of them is the fact that “The Gang Goes to a Water Park.” It wasn’t the first time they left Paddy’s, but it ranks pretty high.
Dennis’ plot line is the strongest, and Frank and Charlie’s is funny if not also repetitive, but the highlight of the episode is the simplicity of Mac and Dee trapped in a water slide with kid after kid mounting up behind them. Dee’s at her best when she’s being bossy, especially when she’s paired up with the character whose peers have outright called him the bossiest member of the Gang.
5 “PTSDee” (Season 12, Ep 7)
Featuring bar none Dee’s lowest point, “PTSDee” is a massively underrated episode. The Mac and Frank VR plotline hasn’t become many fans’ favorite, but it’s solid.
The Dennis and Charlie plotline, where the former becomes a male stripper with Charlie serving as his ‘Boy,’ is the episode’s funniest, but it’s Dee who owns the episode. Why? Because she concocts an elaborate scheme to get a professional male stripper who referred to her as his ‘Rock bottom’ to humiliate himself. How? By swinging his genitals in his daughter’s face.
4 “The Gang Escapes” (Season 13, Ep 2)
The episode that follows “The Gang Escapes,” “The Gang Beats Boggs: Ladies’ Reboot” is more of a Dee-focused episode, but there’s a night and day difference in quality. And, perhaps more importantly, the episode makes Dee the only one to escape from Dennis’ horrifying pleasure room. ‘The only one.’
The episode finds Dee introducing the Gang to the concept of an Escape Room (which Dennis either has heard of or has sadistically imagined). But, once in the Escape Room, AKA Dennis’ apartment, the guys can’t agree on anything, outside the decision to lock Dee away.
3 “Dee Day” (Season 14, Ep 3)
Should It’s Always Sunny get a movie? No. But, if it were to come to fruition, it wouldn’t be the worst idea to start off with one of the Gang’s personal days.
Meaning, one of the days where all of the Gang is personally subjected to one member’s wills and whims. For instance, “Dee Day,” an (unfortunately pulled) episode that’s almost as hysterical as Season 9’s “Mac Day.”
2 “The Gang Chokes” (Season 14, Ep 4)
“The Gang Chokes” has Frank feeling alone and betrayed by the Gang. His volatile reaction is met with ambivalence from Dennis and Mac, but, of course, Charlie takes interest.
But it’s Dee who has the biggest reaction to Frank nearly dying. Specifically, she becomes like Evil Knievel just without an audience or any sense of precaution. Plus, more ‘suicidal race bating.’
1 “The Gang Buys a Roller Rink” (Season 15, Ep 3)
It’s Always Sunny is still going strong, constantly finding ways to reinvent itself, including its own characters’ histories. Take “The Gang Buys a Roller Rink,” which takes the Gang and the viewer back to the ’90s.
Mac nearly runs away with the episode, with his gun handle (sans barrel or bullets) and constant utterance of ‘Mark my words.’ But, the episode’s reinvention of Dee as a once-super-nice person is too great to not be the winner. But, that’s also because of her head-smashing and personality-altering outcome in the episode.
