Interview: Funnyman Michael Showalter gets serious about his directing work in ‘The Dropout’ and more [VIDEO]

Who knew that the same man who gave us The Michael Showalter Showalter would be the same person who goes on to direct the most recent Best Actress Academy Award winner (Jessica Chastain in The Eyes of Tammy Faye) and two other series’ which could garner multiple Emmy nominations this year. Well, if one had taken a second and examined Michael Showalter’s path toward this fantastic string of success, it would come as no shock. He grew up in Princeton, New Jersey. His mother is an author, feminist literary critic, and English and 18th Century French Literature professor. His sister ended up becoming a professional speech writer. Which is to say, he came from a family of high achievers. 

Michael Showalter completed his undergraduate work at New York University and joined a sketch comedy group named The New Group before transferring to Brown University so he could complete his studies. The New Group eventually became known as The State, and their short videos were featured on the MTV show, You Wrote, You Watch It, hosted by then up-and-coming comedian Jon Stewart. 

What’s striking is that no matter what level of success he achieved, Showalter was never satisfied. He would have small parts in film and television, but he was always going for the next thing. He wrote and directed his first film in 2005, The Baxter, starring Michelle Williams, Justin Theroux and Elizabeth Banks received praise from critics. Not bad for his first feature project. 

However, it didn’t take too long for this pattern to continue, and he attempted to write a memoir about how hard it is to write a memoir. He even managed to land a record deal for his stand-up comedy. 

Showalter began seeking projects that allowed him to write, direct, or both. Getting to act in a project became less critical. Showalter and writer David Wain teamed up and went on to write They Came Together, Wet Hot American Summer: First Day of Camp, and Wet Hot American Summer: 10 Years Later. His long, winding journey from his days at The State, producing short videos, standup, The Baxter, and writing with Wain led to his big breakout in 2015 as a writer and director. Hello, My Name is Doris debuted at SXSW and earned critical acclaim, which resulted in Roadside Attractions picking the film up. Going from short videos to critically acclaimed releases would shock some but not those who have had any interaction with this native of Princeton, New Jersey. 

He followed up Hello, My Name is Doris with The Big Sick, which received heaps of praise from critics and earned an Oscar nomination for its screenplay written by Kumail Nanjiani and Emily V. Gordon. Are these successes coincidences, or does it speak to Showalter’s talent to bring out the best in his actor? Showalter touches on this in the interview and credits it to the collaborative environment he fosters at the helm. 

While The Lovebirds didn’t get a deserved theatrical release in 2021 because of COVID, The Eyes of Tammy Faye did, which led to Jessica Chastain winning her first Oscar. For some, this level of success would be plenty, but not many are driven like Showalter. He took the helm of Hulu’s The Dropout, directing four episodes of A Shrink Next Door, an episode of Showtime’s I Love That For You, and another feature film called Spoiler Alert starring Jim Parsons. Would anyone be shocked if all those projects got some Emmy nominations and if Parsons’s latest project became an award season darling next year? Not if Michael Showalter is involved. 

Michael Showalter is Emmy eligible for Outstanding Directing for a Limited or Anthology Series or Movie for the episode “Green Juice” of The Dropout and Outstanding Directing for a Comedy Series for the pilot episode of I Love That For You (“Gottahaveit”).

Photos: Brouk Peters; Beth Dubber/Hulu; Showtime

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Dewey Singleton

I'm a member of Critics Choice, Hollywood Critics Association, and The Society of Professional Journalists. I am also on Rotten Tomatoes. My bylines include @awardswatch, @deweysmovies, @awardsradar, @weliveentertainment, @bleedingcool, and @insessionfilm. I am married to @sgitw and have two sons.

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