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In 2019, Hahn began starring in the title role of HBO's comedy-drama series Mrs. Fletcher.

In 2018, Hahn starred in the drama film Private Life, directed by Tamara Jenkins. She received critical acclaim for her performance. She also began appearing in television commercials for Chrysler, provided the voice of character Ericka Van Helsing in the animated comedy Hotel Transylvania 3: Summer Vacation, and had a voice role in the film Spider-Man: Into the Spider-Verse, as a female version of Doctor Octopus, named Olivia Octavius.

In 2016 Hahn appeared alongside Viggo Mortensen in the drama film Captain Fantastic, and starred alongside Mila Kunis, Christina Applegate, Kristen Bell and Jada Pinkett Smith in the comedy film Bad Moms. IndieWire's Kate Erbland gave the film a B–, noting that it "boasts some good jokes but Hahn's revelatory performance is the big draw." She next appeared in the Amazon comedy pilot I Love Dick, based on the novel by the same name by Chris Kraus and directed by Jill Soloway. It premiered on August 19, 2016.

In 2014 Hahn was cast as Rabbi Raquel Fein in the Amazon Studios critically acclaimed dark comedy-drama Transparent, whose creator, Jill Soloway, had directed her in Afternoon Delight. She received an Emmy nomination for Outstanding Supporting Actress in a Comedy Series (2017) as well as a Screen Actors Guild Award nomination along with the cast. In 2015 she starred alongside Steve Coogan in the Showtime comedy-drama Happyish, but the show was canceled after a single season. That year Hahn co-starred alongside George Clooney and Hugh Laurie in the science-fiction adventure film Tomorrowland, and starred in the box-office horror hit The Visit.

As a lead actress, Hahn starred in the 2013 comedy-drama film Afternoon Delight, directed by Jill Soloway, and 2018's Private Life, directed by Tamara Jenkins, receiving critical acclaim. She had a starring role in the comedy film Bad Moms (2016), and its sequel, A Bad Moms Christmas (2017). She has also appeared in a number of dramatic films, including Revolutionary Road (2008), This Is Where I Leave You (2014), Tomorrowland (2015), The Visit (2015), and Captain Fantastic (2016). In 2017 she received a nomination for a Primetime Emmy Award for Outstanding Supporting Actress in a Comedy Series for her work in Transparent (2014–19).

In 2013 Hahn played her first leading role, in the comedy-drama film Afternoon Delight, which was written and directed by Jill Soloway. The film premiered at the 2013 Sundance Film Festival. For her role, she was nominated for the Gotham Independent Film Award for Breakthrough Actor. Later that year Hahn appeared opposite Jennifer Aniston (her co-star in Wanderlust) in the box-office hit We're the Millers and co-starred alongside Ben Stiller and Kristen Wiig in The Secret Life of Walter Mitty. In 2014 she starred in the comedy film Bad Words alongside Jason Bateman, the ensemble comedy-drama This Is Where I Leave You, and Peter Bogdanovich's She's Funny That Way alongside Owen Wilson.

She received a 2012 Critics' Choice Television Award nomination for Best Guest Performer in a Comedy Series for her performance in Parks and Recreation.

On television, Hahn starred alongside Hank Azaria in the short-lived NBC comedy series Free Agents, a 2011 remake of the British series of the same name. She had recurring roles on HBO shows Hung and Girls. From 2012 to 2015, she received praise for her recurring role on the NBC comedy series Parks and Recreation as Jennifer Barkley, the campaign manager of Leslie Knope's (Amy Poehler) opponent Bobby Newport (Paul Rudd). (She had previously costarred with Rudd in Our Idiot Brother, How Do You Know, and Wanderlust.)

Hahn's first appearance on any television program was Hickory Hideout, a local puppet show for children for then-NBC owned-and-operated station WKYC in Cleveland. (By the time of its cancellation, Hickory Hideout was airing across all of NBC's O&O stations.) While attending a festival, she was introduced to creator/producer Tim Kring. Hahn impressed Kring so favorably that he created the character of Lily Lebowski in Crossing Jordan specifically for her. The series aired from 2001 to 2007. Hahn has said of meeting Kring, "NBC and Tim Kring took a huge leap of faith in casting me. To be worked into a show that was in production and on the schedule is an amazing stroke of luck." On October 21, 2008, TV Guide reported that Hahn had signed a talent holding deal with Fox.

Hahn is married to actor Ethan Sandler. The couple reside in Los Angeles and have two children: a son, Leonard (b. 2006) and a daughter, Mae (b. 2009).

In 2003, Hahn appeared in a supporting role alongside Kate Hudson and Matthew McConaughey in the romantic comedy film How to Lose a Guy in 10 Days. The following year she appeared in Win a Date with Tad Hamilton!, Anchorman: The Legend of Ron Burgundy, Around the Bend, and Wake Up, Ron Burgundy: The Lost Movie. She later had more supporting roles in films, including the 2005 romantic comedy-drama A Lot like Love starring Ashton Kutcher and Amanda Peet; The Holiday (2006) with Cameron Diaz; the science fiction adventure drama The Last Mimzy (2007) alongside Rainn Wilson; Step Brothers (2008); Revolutionary Road (2008) starring Leonardo DiCaprio and Kate Winslet; and The Goods: Live Hard, Sell Hard (2009), How Do You Know (2010), Our Idiot Brother (2011), and Wanderlust (2012).

Kathryn Hahn (born July 23, 1973) is an American actress and comedian. She began her career on television, playing Lily Lebowski in the NBC crime drama series Crossing Jordan (2001–07). Hahn went on to appear as a supporting actress in a number of major comedy films, including roles in the films How to Lose a Guy in 10 Days (2003), Anchorman: The Legend of Ron Burgundy (2004), Step Brothers (2008), Our Idiot Brother (2011), We're the Millers (2013), and The Secret Life of Walter Mitty (2013).