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Olivia Wilde talks about her love for ‘Booksmart,’ Jason Sudeikis and Kansas City

The Making Of: Booksmart

Booksmart is an unfiltered comedy about high school best friends and the bonds we create that last a lifetime. Capturing the spirit of our times, the film is a coming of age story for a new generation.
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Booksmart is an unfiltered comedy about high school best friends and the bonds we create that last a lifetime. Capturing the spirit of our times, the film is a coming of age story for a new generation.

Teens continually surprised Olivia Wilde while she was directing her new acclaimed comedy, “Booksmart.”

“I learned a lot about how much better students are today than they were in my day,” Wilde says. “I didn’t think I’d be saying the words ‘in my day’ already at 35, but that’s how quickly society has evolved.

“In the last 18 years since I was in high school, it’s a completely different world. I was able to learn how much more evolved, how fluid, how political, how smart, how plugged in this generation is in a way that really inspired me.”

That inspiration flows through Wilde’s directorial debut, hitting theaters Friday. The seasoned actress delivers a lively and hilarious romp that could become a generational anthem for Gen Z.

Wilde may be best known to Kansas Citians because of her fiance, Overland Park actor/comedian Jason Sudeikis. They’ve dated since 2013 and are the parents of two young children, Otis and Daisy. She occasionally accompanies him on trips to his hometown and will be a guest at next month’s Big Slick Celebrity Weekend, which he co-hosts.

In “Booksmart,” she cast Sudeikis as a high school principal. But the focus is on Molly (Beanie Feldstein) and Amy (Kaitlyn Dever), two scholarly seniors who realize they’ve forsaken all teenage fun while working toward securing their dream colleges. They vow to fit the missing years of letting loose into the final night before graduation.

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Directing “Booksmart,” Olivia Wilde said she learned plenty from her young stars, Kaitlyn Dever, left, and Beanie Feldstein. Francois Duhamel Annapurna Pictures

Wilde calls it “the ‘Training Day’ of high school movies.” That’s how she pitched it to Annapurna Pictures, the studio best known for prestige hits “Vice” and “If Beale Street Could Talk.”

“What I meant was we have to acknowledge the high stakes of high school,” Wilde says during a phone interview from Los Angeles. “So many of these high school films don’t recognize how intense the experience of it is. Often there’s that buddy, that friend, who allows you to survive. I love the analogy to a buddy-cop movie — like ‘Lethal Weapon’ — where it’s two very different personalities who have each other’s backs.”

Sudeikis plays Principal Brown, a bearded, sweater vest wearing administrator who’s unconcerned with his professional responsibilities.

“Jason is one of the world’s best improvisers,” she says of the “Saturday Night Live” veteran. “I’ve been onstage with him in several situations, and I always just marvel at his skill. He has lightning fast instincts. … He’s very flexible with his creative energy. That’s what I wanted from everybody on set.”

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Olivia Wilde cast her fiance, Jason Sudeikis, as the high school principal in “Booksmart.” Francois Duhamel Annapurna Pictures

A native New Yorker who holds dual citizenship in Ireland, she was born Olivia Jane Cockburn but took the stage name Wilde in homage to playwright Oscar Wilde.

She says she had strong friendships in high school but no Molly/Amy bond with just one friend. Instead she had several intense relationships.

“I’m still friends with all those people, so it’s great to show them this movie. They can all kind of see themselves in it. We all bond on the fact these friendships are what got us through the turmoil of adolescence,” she says.

Wilde attended Phillips Academy Andover, an academically competitive boarding school in Massachusetts.

“I had a passion about theater, but I also loved sports,” she says. “I was very social, but I also hung around with my teachers. I loved books, but I also loved to just hang out. People couldn’t figure me out. Part of what I’m saying with this film is, ‘Stop doing this to each other.’ If you’re categorizing everyone else, you’re definitely doing it to yourself.”

Wilde had to deal with categorization throughout her initial career.

She first gained the attention of viewers as a cast member of the Fox TV drama “House” and gradually transitioned to feature films. After mostly being relegated to eye-candy roles in blockbusters such as “Tron: Legacy” and “Cowboys & Aliens,” Wilde expanded to comedy (“The Incredible Burt Wonderstone”) and weightier drama (“Her,” “Rush”). She likewise began taking more interest in behind-the-camera roles, gleaning tips from a variety of A-list filmmakers she worked with.

She names Martin Scorsese as her biggest on-set influence, working with him as a cast member on his HBO series “Vinyl.”

“Scorsese’s trick of having everyone be off-book” — meaning they had to learn their lines before arriving on set. “It’s not even a trick; it’s just a high standard — but it sets actors free. Additionally, I learned to allow the actors to rehearse on location. It’s not always possible, but it really is a game-changer. Especially if that location is to be their home, it’s a tragedy when actors are brought onto the set five seconds before they’re about to shoot,” she says.

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In “Booksmart,” best friends Amy (Kaitlyn Dever, left) and Molly (Beanie Feldstein) decide they’ve been too studious in high school and need to party. Francois Duhamel Annapurna Pictures

In a recent New York Times feature, “Her” director Spike Jonze said of Wilde, “She’s very unprecious. … She’s driven, really, by an excitement to make things and to learn, and to try things she doesn’t know how to do.”

Like Jonze, her passion for filmmaking got cultivated by directing music videos, leading to endeavors with Red Hot Chili Peppers and Edward Sharpe and the Magnetic Zeros. Last year, she earned the opportunity to helm “Booksmart,” a script (eventually credited to Emily Halpern, Sarah Haskins, Katie Silberman and Susanna Fogel) that had floated around Hollywood for a decade.

The film premiered at the South By Southwest Film Festival in March. Currently, it holds a 100% positive rating on the review aggregator Rotten Tomatoes.

“It definitely does reflect my style,” she says, citing an unbroken sequence at a pool party as the scene she’s most proud of.

“My style will be defined by taking advantage of the opportunities the medium offers. By that I mean, I don’t see a reason to make a narrative feature unless you really use the tools of cinema. I love the opportunity to go outside the box — like, magical realism is a way to illustrate internal thoughts and ideas and emotions.”

The filmmaker often gets a dose of grounded realism when she accompanies Sudeikis on his returns to KC. Her most recent visit was in November when he hosted the Thundergong! charity event at the Uptown Theater benefiting the Steps of Faith Foundation.

“What a magical night. I loved hanging out at that venue,” she says. “I love live music and seeing shows, and Kansas City obviously has this incredible history of music. I’ve had so much fun – whether it’s Big Slick or Thundergong! – we’ve had so many great nights there.”

She’ll be back for Big Slick June 7-8. The yearly charity event for Children’s Mercy Hospital is hosted by Sudeikis and fellow KC luminaries Paul Rudd, Rob Riggle, Eric Stonestreet and David Koechner.

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Actress Olivia Wilde is no stranger to Big Slick. She meets with the patients at Children’s Mercy along with Big Slick hosts (including actor Paul Rudd, pictured, and her fiance, Jason Sudeikis). David Eulitt The Kansas City Star

“I love getting to go to Children’s Mercy Hospital and spending time with the families, nurses and doctors, who are just incredible. It’s changed my life to see the commitment and devotion to children’s health. If only there were more hospitals like it around the country. And I’m really inspired by the donors who keep it going,” she says.

Next up, Wilde is collaborating on another film with Silberman she describes as a “female two-hander comedy.”

Will she shoot this follow-up project in Kansas City?

“Wouldn’t that be cool?,” she responds. “We’d sure get some good catering. Some good barbeque.”

Jon Niccum is a filmmaker, freelance writer and author of “The Worst Gig: From Psycho Fans to Stage Riots, Famous Musicians Tell All.”

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