The Olivia Wilde Movies Ranked

You may look at the title of this article and think “How can you rank two movies? Olivia Wilde has only made two movies.” To that, I respond that Olivia Wilde, a buzzy director on the heels of a well-known acting career turned controversial tabloid figure, has made two features. But since 2011, she has made two shorts in addition to the two longer movies. And when I evaluate a filmmaker’s work, I include the short-form entries into their filmography; I think they further illustrate their oeuvre (been a while since I used that word), and indeed, there are times that shorts are better than features. As you’ll soon see, that’s not the case with Wilde, but they still paint the picture of what she’s done as a director.

At first, what Wilde did as a director wasn’t very promising. Both of her shorts were commission pieces, and FREE HUGS, being her first director’s credit of any kind, was for the magazine Glamour. The comedy, which follows a miserable woman dealing with a breakup, also features some very overt product placement/references to the Clarisonic skincare device, which I understand is no more. So for that reason and others, FREE HUGS is very of its time. It’s part of a trend of shorts, movies, and TV shows that really doubled down on characters that aren’t very likable for the sake of comedy. Maybe IT’S ALWAYS SUNNY IN PHILADELPHIA (2005-present) can pull it off, but Wilde, in her first time behind the camera, certainly couldn’t. Tonally, FREE HUGS is all over the place, and the jokes quite simply don’t land. Wilde pulls in Justin Long and Aziz Ansari as supplementary characters in this 24 minute affair (the former is much better than the latter in this context), but lead Jaclyn Jonet isn’t able to bring the humor out of her depressed but also angry character. FREE HUGS has shades of visual creativity, from its opening tracking on a grocery store conveyor belt to the framing of a workout tape on an old TV, but it’s mostly cringe without the comedy.

Wilde’s other near-commercial short, WAKE UP, was funded by HP. In it, a woman (Margaret Qualley) escapes from her hospital bed to run around the city and dance and wonder at people staring at their screens and devices. I saw the twist coming and the kicker of the HP logo at the end is (unintentionally) hilarious after the short’s faux-profound commentary on people’s obsession with their phones. Wilde has made two comedies and two “artsy” serious films (in both cases, one short and one feature) and WAKE UP falls in the latter camp, albeit not proficiently. There are some good shots here and there, but WAKE UP ultimately feels part of the trend of “soul-stirring” advertisements rather than a really compelling piece of filmmaking.

Now, for all of my negative criticism of Wilde so far, I’ll actually defend her in the case of DON’T WORRY DARLING, the product of her fall from grace after the success of and infatuation with the director’s debut feature BOOKSMART. If you drown out all the production and media drama, from the Shia LaBeouf recasting (although it is certainly understandable to focus on Wilde’s bizarre throwing under the bus of/defense of/plea for LaBeouf, a known abuser, to come back to the movie) to the Florence Pugh relationship to the Harry Styles romancing amid/following a breakup with Jason Sudeikis to Cannes hullabaloo and a probably fake Styles spit on costar Chris Pine…OK, that’s a lot to drown out, and there’s even more. But in trying to just focus on the movie, on DON’T WORRY DARLING as a work of art, I came to the conclusion that it’s…just fine. The sophomore slump is a tale as old as time, and I do think Wilde fell into the trap of indulgence that can come after an initial, big success. But for all its messiness, I think the movie is generally an engaging watch with some brilliant images. A number are cribbed from influences such as David Lynch and other practitioners of “something funky’s going on in suburbia,” but I think Wilde is unfairly coming under fire for such a practice when every other A24 dude is doing the same. It’s true that Styles is a wet blanket on every scene, although the criticism of his obvious British accent in an American setting is baseless once you watch the movie (but I do think the plot point that justifies it was written in to provide cover for him not attempting an American accent). And DON’T WORRY DARLING’s ultimate twist, while with some merit, didn’t quite satisfy me after the mysterious build-up. But Florence Pugh and Chris Pine are equal matches in their strong performances and I felt that the whole thrust of DON’T WORRY DARLING, while not exactly groundbreaking in its commentary or how it executed it, is moderately unsettling and compelling.

From outright revulsion to lukewarm reception: so far, I may have painted the picture that Wilde isn’t a very good director. And while I think her shorts leave very much to be desired and DON’T WORRY DARLING may be a slight disappointment, it was her first feature (released eight years after her first short) that made me and most anyone care about her follow up. BOOKSMART is a phenomenal coming-of-age comedy, often described as a “female-led SUPERBAD” (2007). While I think the comparison is apt, as the movie owes a lot to the studio comedies of the previous decade, BOOKSMART is also capable of standing on its own as a hilarious, heartwarming movie. As someone who was never, like, a huge fan of Olivia Wilde the actor, BOOKSMART, as my and most everyone’s introduction to Olivia Wilde the director, was a huge and pleasant surprise. Beanie Feldstein (the sister of Jonah Hill, in a further comparison to SUPERBAD and the masculine comedies of its era) and Kaitlyn Dever have great chemistry and play off each other so well, while the supporting characters weave in and out of the movie with comic aplomb. Especially in an era of studio comedies often lacking in quality, BOOKSMART is a standout piece, inspiring constant laughter as well as empathy for its characters. BOOKSMART may have been a fluke; time will tell, but for now, it’s clearly Olivia Wilde’s best film as director.

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