Kaitlin Olson has established herself as a fearless and dynamic presence in television over the past two decades, captivating audiences with roles that range from chaotic comedy to compelling drama. Known for her ability to infuse every character with a unique blend of sharp wit and raw humanity, Olson’s body of work reveals a versatility that spans animated satire, dark comedy, and procedural drama. This list ranks her ten most significant television roles, highlighting the breadth and depth of Kaitlin Olson TV roles throughout her career.
Debbie in ‘Out of Practice’: Early Network Sitcom Appeal
Premiering in 2005, Out of Practice is a comedy centered around a family of high-achieving doctors and the tension that arises from their professional and personal intertwining lives. Olson played Debbie, a supporting character adding a hint of quirky charm during the show‘s hospital and family scenes. Despite her role being relatively minor, it showcased Olson’s comedic timing early in her career. The series benefited from its seasoned creators, including Frasier producers Joe Keenan and Christopher Lloyd, and presented Olson alongside established talents such as Ty Burrell and Jennifer Tilly.
Becky in ‘Curb Your Enthusiasm’: A Recurring Role in HBO’s Social Satire
Appearing intermittently between 2000 and 2020, Olson portrayed Becky on HBO’s Curb Your Enthusiasm, a semi-improvised comedy that follows Larry David’s misadventures through awkward social situations. Becky’s introduction in the memorable Beloved Aunt episode placed Olson in the midst of a storyline involving a botched funeral and public relations fiasco. Her role as Cheryl Hines’ sister allowed Olson to integrate seamlessly into a high-profile cast that included Larry David and Jeff Garlin, exposing her to HBO’s signature brand of sharp, character-driven humor.
Ethel in ‘Brickleberry’: Grounding a Wildly Irreverent Animated Series
From 2013 to 2015, Olson voiced Ethel Anderson in the animated series Brickleberry, which focuses on a group of inept park rangers in a fictional national park. Ethel is a capable ranger with a chaotic streak, who often serves as the voice of relative sanity amid the show’s outrageous antics. Olson’s portrayal during the first season established the character’s grounding element before Natasha Leggero took over the role in later seasons. Her voice work balanced intelligence and indulgence within the show’s politically incorrect and raunchy humor.
Dual Characters Carol and Danielle in ‘Unsupervised’: Complex Voices in an Animated Comedy
In 2012’s animated series Unsupervised, Olson voiced two distinct characters—Carol, an apathetic and pot-smoking stepmother, and Danielle, a teenage high schooler nicknamed Rocket Tits. The series depicts two teenagers navigating adolescence without much parental direction, highlighting themes of dysfunction and sincerity. Olson’s vocal performances capture both characters’ detachment and edge, with Carol’s neglect underscoring the lead character Gary’s misplaced optimism, and Danielle embodying teenage rebellion with a magnetic carefree attitude.
CeCe Ryder in ‘Agent Elvis’: A Satirical Spy Role in Adult Animation
In 2023, Olson lent her voice to CeCe Ryder, a sharp and high-ranking government agent in the adult-animated series Agent Elvis. The show imagines Elvis Presley as a secret agent combating conspiracies while continuing his music career. CeCe functions as Elvis’s handler and occasional moral compass, navigating covert missions and managing his wild behavior. Though the show was canceled after one season, Olson’s role was central to its blend of espionage and satirical humor, anchoring the series’ sharp and absurd tone.
Cricket Melfi in ‘Flipped’: A Quirky Lead in Short-Form Comedy
In the 2020 comedy Flipped, Olson stars as Cricket Melfi, half of a delusional couple attempting to become home renovation stars but instead entangled with a cartel after finding hidden money. The show’s fast-paced, short episodes feature Olson as a perfectionist whose chaotic energy and creativity contrast with the dangerous circumstances. Olson’s performance alongside Will Forte delivers a dynamic mix of humor and tenderness, earning her a Primetime Emmy nomination for Outstanding Actress in a Short Form Comedy or Drama Series.
DJ Vance in ‘Hacks’: Demonstrating Dramatic Depth in a Critically Acclaimed Series
Since 2021, Olson has played DJ Vance on the acclaimed comedy Hacks, portraying the daughter of Deborah Vance, a fading Las Vegas performer. DJ is a recovering addict and entrepreneur, whose sporadic but emotionally charged appearances add complexity to the show’s exploration of generational conflict and the difficulties of maintaining comedic relevance. Olson’s portrayal of DJ offers a raw and vulnerable performance, providing poignant moments alongside the series’ leads Jean Smart and Hannah Einbinder.
Morgan Gillory in ‘High Potential’: A Unique Mix of Crime and Personal Struggle
Currently airing on ABC, High Potential stars Olson as Morgan Gillory, a single mother with an exceptional IQ who works as a janitor for the LAPD before becoming a civilian consultant after solving a murder. The crime dramedy combines weekly mysteries with Morgan’s personal quest to find her missing ex-husband. Critics laud Olson’s portrayal as smart and emotionally rich, comparing her performance to celebrated TV detectives but emphasizing her character’s relatable imperfections amidst professional chaos.
Mackenzie “Mickey” Molng in ‘The Mick’: A Role Defying Conventional Comedy
Olson led the series The Mick from 2017 to 2018, playing Mickey Molng, a brash, foul-mouthed woman who suddenly assumes guardianship of her wealthy sister’s spoiled children after their parents disappear due to fraud charges. Set in a Connecticut mansion, the sitcom revolves around Mickey’s unconventional approaches to parenting, filled with profanity and misguided but sincere efforts. The show, though short-lived, earned critical praise for Olson’s turbulent and unapologetic performance, which continues to resonate with fans.
Dee Reynolds in ‘It’s Always Sunny in Philadelphia’: The Role That Defined a Career
Since 2005, Olson has been iconic as Dee Reynolds on the long-running sitcom It’s Always Sunny in Philadelphia. The series follows five morally corrupt friends managing a dive bar in South Philadelphia and engaging in endless chaotic schemes. Dee begins as the group’s supposed voice of reason before descending into the same delusional and narcissistic behavior. Olson’s portrayal highlights her fearless physical comedy and vocal range, helping shape the show’s evolution from cult hit to television staple and earning continuous critical acclaim for her boundary-pushing performance.
Kaitlin Olson’s career demonstrates remarkable adaptability across genres, from animation to live-action, comedy to drama. Her fearless approach to complex and often flawed characters has made her one of the most compelling actresses in contemporary television. Whether grounding a wild animated series or delivering gut-wrenching vulnerability in a dramatic role, Olson continues to captivate viewers, showing that her best performances—and the surprises in her career—are yet to come.
