10 Greatest Actors Turned Directors

10. Olivia Wilde

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She has thus far directed only one feature film, but what a film it is. Olivia Wilde’s career up to 2019 had been solid if perhaps unspectacular - after bursting onto the scene with a recurring role in The O.C, she had found a few decent film roles as well as some less interesting ones, and a lead part in HBO drama Vinyl which, despite input from Martin Scorsese and Mick Jagger, promptly bombed.

Then, she directed Booksmart. One of the sharpest, funniest, and generally most delightful films in recent memory, the comedy quickly changed Wilde’s status, and most likely her career going forward.

An unflinching look at friendship, young adulthood, self confidence and sexuality, Booksmart was starmaking not just for its lead actors Kaitlyn Denver and Beanie Feldstein but for its director too. A sleeper hit and a critical smash, it left audiences and studios alike eager for Wilde’s next effort.

She has also recently been involved in documentaries, producing and directing shorts with heavy subjects like war and natural disasters. While they may not have the mass appeal of a coming of age comedy, she is evidently a director to watch in future.

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Joshua H. Mills likes Milhouse Van Houten, Tom Waits, and A Confederacy Of Dunces. You can find his content at, and enjoy his 15 tweets @jharrymills