Kristen Wiig Was Neck-and-Neck With Kailtin Olson for the Part of Dee on ‘It’s Always Sunny in Philadelphia’
In an alternate timeline, Kaitlin Olson spent seven years as one of the most beloved cast members in Saturday Night Live history and Kristen Wiig constantly needs to remind herself that her husband and Ryan Reynolds are “just friends.”
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The role of Deandre “Sweet Dee” Reynolds on It’s Always Sunny in Philadelphia is one of those parts that, 16 seasons into the longest-running live-action sitcom in American television history, you can’t imagine could ever have been pulled off by anyone besides Olson. Much like how Michael Scott on The Office would have been unrecognizable if Bob Odenkirk nailed his audition and Steve Carell slept in that day, Olson’s contributions to the character elevated Dee far above the lines in the script and turned her into a completely different comedy beast from what Rob McElhenney, Glenn Howerton and Charlie Day originally under-wrote for Dennis’ denigrated twin sister.
Many Always Sunny fans know that, in the original, low-budget and unaired pilot for the show, the role of Dee was played by McElhenney’s soon-to-be ex-girlfriend Jordan Reid. But, when the series got picked up, the breakup forced McElhenney, Howerton and Day to recast Reid’s character, narrowing down the potential replacements to Wiig and Olson.
Though it’s easy to lament Wiig’s luck that, despite her massive talent, McElhenney’s future wife and the woman born to play the role beat out Wiig for the opportunity of a lifetime, don’t feel too bad. Less than a year later, Wiig was on SNL where no one ever set her on fire — twice.
In a 2015 article from BuzzFeed News, Howerton revealed that the final two actresses considered to join It's Always Sunny in Philadelphia were Olson and Wiig, explaining that he already had some familiarity with the eventual victor from her then-most popular TV role. “I knew her work from seeing her in Curb,” Howerton said of Olson, explaining of the selection process for the next Dee. “We wanted to find somebody who could be as funny as the guys, and we felt a lot of times in comedies, girls are so often relegated to the ‘oh, you guys’ role.”
However, as Olson would later reveal, the sides that McElhenney, Howerton and Day gave her during the audition had to be repurposed from one of the scenes between “the guys” because there wasn’t enough for Dee to do in the original Always Sunny pilot script for an actress to prove herself in a callback. And when the Always Sunny creators offered Olson the role of Dee, Olson initially turned it down because she considered what the men had written to be exactly the “oh, you guys” role Howerton wanted to avoid.
Thankfully for Always Sunny, McElhenney, Howerton and Day promised to rewrite the character to give Olson the opportunity to shine, and they succeeded in convincing her to give Always Sunny a shot. And, thankfully for Wiig, the second-place finisher found a spot in the most sought-after workplace in comedy mere months after Olson won the role of Dee.
Nearly 20 years later, the casting decision worked out for all parties involved — though it’s fun to imagine a world where the Target Lady is Paddy’s Pub’s most punished target.
