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Always Sunny: Sweet Dee's Sweet 16 – Happy B'Day, Kaitlin Olson!

In honor of It's Always Sunny in Philadelphia star Kaitlin Olson's birthday, we have "Sweet Dee's Sweet 16" - our top Dee Reynolds episodes.


We can't think of a better day than today for a special edition of "The 'Always Sunny' Strike Survival Guide," our between-seasons look at how things are going with FXX's Rob McElhenney, Charlie Day, Glenn Howerton, Kaitlin Olson & Danny DeVito-starring It's Always Sunny in Philadelphia as the SAG-AFTRA & WGA strikes roll on. And why's today so special? Because today is Olson's birthday – so in honor of that, I'm taking a look at 16 seasons worth of "Deandra 'Sweet Dee'/'Dee' Reynolds" greatness. What follows are our picks for the best Dee episodes – one from each season. And just so no pitchforks or fiery torches come into play, I will readily admit that there were more than a few tough contenders in a number of seasons. And, yeah… some of these were tough calls. But the one thing that they all have in common and collectively prove is what a true comedic genius Olson is – a true gift to the small screen.

always sunny
IT'S ALWAYS SUNNY IN PHILADELPHIA (Image: FX Networks Screencap/It's Always Sunny in Philadelphia)

It's Always Sunny in Philadelphia: Sweet Dee's Sweet 16

S01E03 "Underage Drinking: A National Concern" (directed by Dan Attias, story by  Charlie Day & Rob McElhenney, and teleplay by Rob McElhenney): Dee's drunken attempts at a high school senior prom do-over is so uncomfortably wonderful.

S02E05 "Hundred Dollar Baby" (directed by Dan Attias and written by Charlie Day & Glenn Howerton & Rob McElhenney): Dee's growing rage and our first true appreciation for how well Olson/Dee and Day/Charlie work together.

S03E09 "Sweet Dee's Dating a Retarded Person" (directed by Jerry Levine, story by  Glenn Howerton, and teleplay by  Scott Marder & Rob Rosell): Dee demonstrates just how truly deep her shallowness runs – with serious "guilty laughs" points for how Olson handled Dee's facial reactions to how her boyfriend was laughing.

S04E11 "The Gang Cracks the Liberty Bell" (directed by Matt Shakman and written by Rob McElhenney & Glenn Howerton & David Hornsby): An episode that I grew to love over time, Olson and David Hornsby continue their great chemistry into a different time period & dynamic.

S05E06 "The World Series Defense" (directed by Randall Einhorn and written by David Hornsby): Dee reading Mac's (McElhenney) "love letter" to Chase Utley. Nuff said.

S06E03 "The Gang Buys a Boat" (directed by Randall Einhorn and written by Charlie Day & Rob McElhenney): The dance that inspired generations – and gave us a better appreciation for P. Diddy.

S07E02 "The Gang Goes to the Jersey Shore" (directed by Matt Shakman and written by Dave Chernin & John Chernin): You can pick pretty much any moment from when Dee's fair tale memories of the Jersey Shore get wiped away by the violent reality of it – but for me? It's Dee's braid getting caught before the ride drop.

S08E05 "The Gang Gets Analyzed" (directed by Todd Biermann and written by Luvh Rakhe): A tie between Dee's "Tell me I'm good" moment with the therapist (Kerri Kenney-Silver) and her over-the-top reaction to being told she has to do the dishes.

S09E06 "The Gang Saves the Day" (directed by Dan Attias and written by Dave Chernin & John Chernin): Want insight into what Dee would be willing to do for a successful sitcom & film career that respects her "unique" skills at doing accents and ends with Josh Groban as her husband, look no further than this sociopathic fever dream.

S10E01 "The Gang Beats Boggs" (directed by Todd Biermann and written by Dave Chernin & John Chernin): Dee's at her best when she's in full-on "Anything they can do, I can do better" mode.

S11E01 "Chardee MacDennis 2: Electric Boogaloo" (directed by Heath Cullens and written by Rob McElhenney & Charlie Day): With the original a close contender in Season 7, the Dee/Dennis (Howerton) is scarily good together when they're on the same page.

S12E02 "The Gang Goes to a Water Park" (directed by Matt Shakman and written by Eric Ledgin): With all due respect to McElhenney, Olson shows how on-point her comedy skills are – even stuck in a water slide tube.

S13E04 "Time's Up for the Gang" (directed by Kat Coiro and written by Megan Ganz): A toss-up between Mac & Dee's "uplifting" moment and watching Dee realize that her time might just be up, too.

S14E02 "Thunder Gun 4: Maximum Cool" (directed by Heath Cullens and written by Conor Galvin): In one focus group, Dee single-handily sets back the feminist movement a half-century – exposing one of Dee's key insecurities in the process.

S15E03 "The Gang Buys a Roller Rink" (directed by Richie Keen and written by Rob Rosell & David Hornsby): It says a lot about Olson as a comedic actress that she had us feeling for the real "Sweet Dee" – even though she would have to fall in order for our "Sweet Dee" to rise.

S16E07 "The Gang Goes Bowling" (directed by Megan Ganz and written by Rob McElhenney & Charlie Day & Glenn Howerton): Every bit of need, insecurity, and doubt – all laid bare in a bowling alley. And while the jury is still out on what (if anything) Dee took away from the experience – for just one tiny but shining little moment? She got a win.


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Ray FlookAbout Ray Flook

Serving as Television Editor since 2018, Ray began five years earlier as a contributing writer/photographer before being brought onto the core BC team in 2017.
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