Kaitlin Olson Has Undergone A Stunning Transformation

In the sitcom realm, the only female member of the main cast of "Seinfeld," Julia Louis-Dreyfus, walked so that Kaitlin Olson could run — straight into a car door after trying to shoplift a pair of shoes. Sure, Elaine Benes wasn't Manhattan's most upstanding citizen, but she didn't fake a baby's funeral, trick a stripper into giving his own daughter a lap dance, or dig up her mother's corpse. These are all storylines Olson was tasked with making funny as Deandra "Sweet Dee" Reynolds on "It's Always Sunny in Philadelphia" — and she met the challenge.

Olson's portrayal of one of the worst people on television earned her bragging rights as one of the stars of the longest-running live-action sitcom. On "It's Always Sunny," Dee and her partners in crime — Frank Reynolds (Danny DeVito), Dennis Reynolds (Glenn Howerton) Charlie Kelly (Charlie Day), and Ronald "Mac" McDonald (Rob McElhenney) — spend a lot of time cooking up schemes within the confines of their Philly dive bar, Paddy's Pub, but Olson grew up surrounded by wide open spaces on her family's farm in Oregon. "I started doing summer camp stuff in elementary school and loved doing the plays," she told BuzzFeed. "I liked making people laugh."

Olson couldn't have dreamed just how many people she'd be making laugh someday. And after years of establishing herself as a comic actor on her irreverent sitcom, she took her talents somewhere unexpected: to a police procedural. The success of her ABC series "High Potential" has made her one of TV's hottest actors, but growing up, Olson wasn't always so popular.

In a "Build Series" interview, Kaitlin Olson explained why comedy legends Carol Burnett and Gilda Radner were her heroes growing up. "I loved watching a woman be so funny and so not worried about what she looked like," she said. Sadly, one of the most tragic moments in Olson's life would force her to focus on her own appearance, thanks to some cruel classmates.

At age 12, Olson crashed her bicycle. Because she didn't have a helmet on, she fractured her skull and had to undergo reconstructive surgery on her face and head. It was tough starting 7th grade with visible injuries and her hair shaved off. " ... Some kids were really mean," she told Glamour. Recalling a particularly painful cafeteria experience, she said, " ... This kid named Casey Johnson was somewhere behind me in line throwing jelly beans at me trying to get them to land in the hole in my head." It was a difficult, lonely time for Olson, who told Vanity Fair that she struggled to make friends. However, it actually set her on a path to become more like those hilarious women she admired. "It forced me to be funny because I wasn't relying on getting through middle school and high school relying on my looks," she explained.

But by high school, Olson had won over some classmates and found a way to give herself a little confidence boost that is totally out of the playbook of her "High Potential" character, Morgan Gillory. "I did all of my friends acrylic nails for prom," she told HoboTrashcan. "I taught myself how to do fake acrylic nails. ... I was really proud of myself."

Kaitlin Olson didn't go too far from her hometown of Tigard, Oregon, when she started college. She was an acting major at the University of Oregon, but knew she had to make a big move to turn her passion into a career. " ... People thought I was crazy in my little tiny town in Oregon to move to Los Angeles and think that I could be a TV star," she told Vanity Fair. "Everyone made fun of me."

She didn't immediately find small-screen success upon arriving in LA, but continued her comedy education as a member of The Groundlings, the esteemed improv troupe that has kick-started many comedy careers. (Fun fact: Olson's "Hacks" co-star Hannah Einbinder is the daughter of Laraine Newman, one of its founding members.) Olson performed alongside another future star during her time with the group — and it turns out that Dax Shepard's cringe behavior was making people uncomfortable even back then. When Olson appeared on his "Armchair Expert" podcast in 2018, Shepard recalled, "Many, many of our sketches had you and I making out." He even suggested that this played a part in his ousting from the theater's Sunday Company. "Yeah, I don't think anybody wanted to see it," Olson agreed, adding, "It made everybody uncomfortable."

Olson also lost her spot with The Groundlings when she wasn't made a member of its main company. "It was very hurtful," she said on "Conan O'Brien Needs a Friend." At least she made some great memories with Shepard; on his podcast, they reminisced about the time he got bitten by a seal on the beach after they did ecstasy.

Kaitlin Olson had to hustle during her time with The Groundlings, telling BuzzFeed she juggled jobs at a salon, boutique, and biotech company to pay her bills. She clearly needed to get paid for what she came to Hollywood to do — make people laugh — and her hard work paid off when she made one of the biggest comedy names in the biz do just that. Some stars have horror stories about their early auditions, but Olson's experience with "Curb Your Enthusiasm" star and creator, Larry David, was a dream. "It was really awesome. It was the first time that I'd been given the freedom to say whatever I wanted," she told HoboTrashcan.

Olson's improv work also received quite the compliment. "I was really proud to make Larry laugh. The more I would yell at him the more he would laugh," she recalled to BuzzFeed. In addition to bragging rights, she scored her first TV role in a 2000 episode of "Curb" during the show's first season. She played Becky, the sister-in-law of the fictional Larry. Her on-screen sibling was another former Groundling: Cheryl Hines, whom David warned not to date Robert F. Kennedy Jr. (that RFK Jr. whale tale is straight out of "It's Always Sunny").

In the pilot for what would eventually become "It's Always Sunny in Philadelphia," Jordan Reid played the female lead. She was dating Rob McElhenney at the time, and they were developing the series with Charlie Day and Glenn Howerton. But Reid's relationship with McElhenney ended, and the search for a new Sweet Dee was on.

Because the character wasn't fully realized, Kaitlin Olson improvised a bit during her audition. She did have lines to read, however, and one that she skipped over happened to be written by McElhenney. "I left the room and Rob was like, 'How did she leave out the funniest line that was in there?' and he didn't want to cast me," she recalled to BuzzFeed. McElhenney admitted to Variety that his bruised ego almost lost him not only a great comedic catch but the future love of his life. "I was 26 years old, and probably very precious with what I was writing," he said.

Olson ultimately beat out another future comedy great, "Saturday Night Live" star Kristen Wiig, for the part, but she had second thoughts when she received some scripts. The lines she read for her audition had been for other characters, and she simply didn't think Sweet Dee was funny enough. McElhenney assured Olson that they would improve the character, and she was just as hilariously offensive as the rest of the gang when Danny DeVito signed on for the show's second season, completing the "It's Always Sunny" crew. In 2025, the "Taxi" icon told Variety, "I've always thought that Kaitlin was the funniest one on the show."

It's not uncommon for actors to fall in love with their co-stars, but professional relationships can get a bit awkward when unrequited feelings are involved. This was the case for Kaitlin Olson, who fell for Rob McElhenney first and made the first move. On "Armchair Expert," she revealed just how wrong this went when she tried to flirt with McElhenney at a party. "I would just ... back up in between his legs," she recalled. "He was like, 'What are you doing?'" She also realized McElhenney was in love with her before he did.

They started dating sometime after the 2006 wedding of their costars Charlie Day and Mary Elizabeth Ellis, and they kept their relationship a secret at first. McElhenney's roomie, Glenn Howerton, didn't even catch on to what was going on. "[Olson] would always come over and then would get too drunk and sleep there. In retrospect, she wasn't really that drunk," Howerton told Variety. One day, as Howerton was cleaning their cats' litter box, McElhenney came clean. Howerton's reaction? "I was like, 'You idiot!"

Olson and McElhenney broke the news to the rest of the cast as a group. "Kaitlin just starts crying and says, 'I love him. I love him so much, you guys. ... We don't want you guys to be mad at us,'" Ellis recalled to BuzzFeed. "It just made us laugh so hard, because it was such a funny way to reveal that they were dating."

Kaitlin Oslon's dedication to her craft has resulted in numerous on-set injuries over the years, including smashing her head into a car so hard that it left a dent in it. "We were like, 'Oh my god, she broke her neck,'" Charlie Day recalled on "The Always Sunny Podcast." Luckily, her injury wasn't that serious, but she has broken her back.

That particular injury didn't happen at work. On "Never Not Funny: The Jimmy Pardo Podcast," Olson said that she had been drinking at an Independence Day rooftop party when an attendee offered to lift her high over his head. "He said he was a football player and used to pick up cheerleaders," she explained. Luckily, her husband-to-be realized that this was not a great idea. "Rob came over and was like, 'Can you not let someone lift you up on the roof of a building?'" Olson recalled. She listened to him, but decided to perform the stunt on the street instead. This resulted in a broken sacrum.

Olson had to film a waterboarding scene at work afterward. "If you see that scene ... both my hands are underneath supporting my back to try and keep the pressure off it," she said. On "The Always Sunny Podcast," she also revealed that the accident happened just two months before her September 2008 wedding. "I wasn't sure if I was gonna be able to walk down the aisle," she told her castmates. That aisle was located in a field, with Glenn Howerton describing the wedding thusly: "It was very reminiscent of being at a keg party in Montgomery, Alabama."

Both of Kaitlin Olson's two birth experiences were pretty unforgettable for some wild reasons. As she was waiting for baby No. 1 to arrive, she was already in labor when she and Rob McElhenney decided to go watch the Phillies play the Dodgers. "I think I made it like five innings? Seven innings? I was like, 'OK, time to go now,'" Olson recalled to Glamour. She and McElhenney welcomed their son Axel on September 1, 2010. If his moniker sounds like one McElhenney's "It's Always Sunny" character would choose, well, he is named after the "Beverly Hills Cop" character Axel Foley.

Kaitlin knew better than to take her unborn son out to the ballgame for her second time at bat two years later, but her birth plan didn't go off without a hitch. She was hoping to have a home birth, just like she had the first time around, but her midwife decided that she needed to be examined by a doctor while she was in labor. "I had to get in the back of her Prius, which is a wonderfully environmental car, but not great for labor in the back seat," Olson said on "Conan." Unfortunately, they got stuck behind a constantly stopping garbage truck on the way there.

Olson didn't have to be admitted to the hospital, so she was able to give birth at home. After almost 24 hours in labor, she and McElhenney welcomed their son Leo on April 5, 2012. "It was a nightmare. I mean, I love him, but it's enough babies," she said.

While "It's Always Sunny in Philadelphia" continued getting renewed season after season, Kaitlin Olson didn't rest on her laurels. She continued seeking employment elsewhere, landing the lead role in the Fox sitcom "The Mick" in 2016. It was another role that required her to have a potty mouth and act like a self-centered jerk at times — but this time, she would be acting alongside children regularly. "I read the script and was like 'Ugh, damn it, I love the script. I want to do it, but I've got to find a way to make it not Sweet Dee,'" she recalled to Vanity Fair. The show ran for two seasons from 2017 to 2018.

Then, in 2021, Olson began appearing on "Hacks" as D.J. Vance (not to be confused with the eyeliner-loving veep, JD Vance). She plays the daughter of Jean Smart's comedian character, and to say that D.J. has mommy issues is putting it mildly. During a roast, D.J. refers to her mother by the c-word over and over again. It was this episode that earned Olson her second Emmy nomination in the guest-starring category (the first was also for "Hacks"). Olson didn't take a statuette home at the 2024 Emmys, but her sense of humor remained intact after the disappointment. "This is a huge relief, because had I won, I would no longer be able to complain loudly and widely about never winning an Emmy," she joked on Instagram.

While the gang has pretended to be cops on "It's Always Sunny in Philadelphia," it was probably hard for some longtime fans to imagine Kaitlin Olson starring in a straight-up police procedural when she got cast in "High Potential." A storyline involving a janitor who gets asked to become a police consultant also sounds like something Charlie would fantasize about while cleaning bathrooms at Paddy's Pub. But according to Olson, the reason she almost passed on the ABC series was the time commitment. "I was enjoying working part of the year and then being a mom the other part of the year," she explained to Esquire. But she had a change of heart after her agent convinced her to read the script — and "High Potential" became one of the most-watched shows of 2025.

Her character, Morgan Gillory, has a high IQ and a razor-sharp memory, so some of the lines Olson has to memorize are definitely a mouthful. Of those evidence info dumps, she joked, "You know how people do crossword puzzles to keep their brains active? There's no risk of Alzheimer's for me." However, she did once use sticky notes when math was involved, saying, "No goddamn way I would've been able to memorize all those numbers."

Morgan's rainbow-hued wardrobe is as brilliant as her mind. When she struts onto a crime scene, she usually has on a miniskirt and heels, and her closet is packed with candy-colored faux furs, bold patterns, and shiny fabrics. "I love that the outfits are wild and unexpected because Morgan is unexpected," Olson said on "Meet Me at the Movies." She also has quite the collection of funky earrings, with Olson revealing in a Facebook video that her favorites are the shrimp-shaped ones. And with her love of acrylic nails, high school Olson would likely love that "High Potential" Olson gets to rock wild new nails in every episode.

While some celebrities struggle to get their children interested in their work, Kaitlin Olson's sons have become such massive fans of "It's Always Sunny in Philadelphia" that she had to start warning them not to repeat any of the show's NSFW content to their classmates as they work through its large catalog of episodes. "Now I have a 13-year-old and a 15-year-old. They watch all of them," she told Esquire in 2025. Like many "It's Always Sunny" fans, they even love shouting the "Dee's a bird!" insult from the show at their mom, Olson revealed on "Late Night with Seth Meyers." They also saw the "Hacks" episode in which she repeats the c-word. "They do love yelling that at me," she said.

Axel and Leo just might follow in their parents' funny footsteps. "The sense of humor they've adapted from us is just so horrifically inappropriate," Olson admitted. However, she and Rob McElhenney aren't on the same page when it comes to their kids appearing on camera. After McElhenney and Ryan Reynolds bought a soccer team, reportedly infuriating Blake Lively in the process, McElhenney allowed the boys to appear in the docuseries about his sports endeavor, "Welcome to Wrexham." Olson didn't sign off on this, telling Variety, "I'm still unhappy about that." But according to McElhenney, the boys had a blast — and in 2025, they made cameos on "It's Always Sunny" as underage drinkers at Paddy's Pub. Sorry, mom!