How ‘Booksmart’ Created A Banner Musical Moment With ‘You Oughta Know’

Olivia Wilde knew she wanted a karaoke scene in “Booksmart,” her dazzling directorial debut about studious best friends who decide to cut loose on the eve of their high school graduation. What better way to embolden an introvert than to put her in a darkened room, hand her a microphone and blare … well, what song should it be?

“You Oughta Know.” That much was obvious.

Wilde was working with writer Katie Silberman (“Set It Up,” “Isn’t It Romantic”) to update the “Booksmart” script, which had languished in development since appearing on the Black List, Hollywood’s official roster of unproduced projects, in 2009. The original version, penned by “Trophy Wife” creators Emily Halpern and Sarah Haskins and first revised in 2014 by Susanna Fogel (“The Spy Who Dumped Me”), offered much of the same premise: Two college-bound BFFs who traded social rites for unwavering academic fanaticism suddenly realize that many of their ostensibly inferior peers were able to juggle both. Initially, the movie’s arc had them resolving to find boyfriends before prom ― a shopworn trope Wilde and Silberman nixed. Instead, the protagonists would commit to a marathon night of partying, proving to themselves and their peers that building impressive résumés isn’t their only skill.

The results are a little more “Superbad” and a lot less “Cinderella.” Over the course of a single evening, Molly (“Lady Bird” breakout Beanie Feldstein) and Amy (“Justified” alum Kaitlyn Dever) bounce from one classmate’s shindig to the next en route to the popular kids’ blowout. Along the way, they suffer travel snafus, bump into their principal (Jason Sudeikis), accidentally get high, attempt to woo budding flames and navigate a run-in with law enforcement. Oh yeah, and there’s karaoke, because what bash is complete without it?

“We were so short on time and we had so little space at the party to have a scene like that, but I knew we had to make the karaoke work,” Wilde said. “We wrote it, actually, first to be a shorter moment.”

During the shoot last May, the sequence became one of the film’s best moments ― a showstopper that marks a major turning point for Amy, who’d previously spent most of the night asking Molly how soon they could go home.

In plotting out the scene, Wilde knew she needed a “classic karaoke song” that would double as a bold choice for a character not known for audacity ― the sort of thing Amy would sing into a hairbrush in her bedroom, perhaps. Wilde immediately thought of “You Oughta Know,” the fiery breakup anthem that vaulted Alanis Morissette’s career. Fearing the rights would be too expensive, she shot the scene using a karaoke version. But after seeing it in the edit room later, she felt the number lacked that signature Alanis oomph.

“I was thinking, ‘Gah, the real song is so much better than the karaoke track, and I really need Alanis in this,’” Wilde recalled. “I need her voice, I need the whole band. You know, Flea [from Red Hot Chili Peppers] plays on that song, and I needed the sound. I called [‘Booksmart’ music supervisor Bryan Ling] and I was like, ‘You’re not going to like this, but I need real Alanis. If she knew what we were saying here, I think she’d really be on board.’”

Wilde wasn’t kidding around. To demonstrate her commitment, she wrote Morissette a letter, joining a slew of A-listers who have recently taken music rights into their own hands. Greta Gerwig wrote to Dave Matthews Band while making “Lady Bird,” Jon Chu wrote to Coldplay for “Crazy Rich Asians,” Bo Burnham wrote to Enya for “Eighth Grade” and Lupita Nyong’o wrote to Taylor Swift for the forthcoming zombie comedy “Little Monsters.” Such memos make for charming anecdotes that unmask the many business maneuvers necessary when piecing together a film of this size. Music rights often require separate licenses from songwriters, producers and the record label, leading to complicated financial deals.

“I was so aware of the power of human connection in a process that can become very quickly corporate,” Wilde said. “When labels and lawyers are involved, you forget that it’s artists just trying to make something together.”

She delivered the letter through Morissette’s manager, explaining the scene in question and describing “Booksmart” as coming-of-age tale that celebrates female friendship.

“I just said how much she had meant to me in my youth and when I was in high school ― ‘Jagged Little Pill,’ in particular,” Wilde said. “Her strength as a woman and an artist and her singularity had really inspired me.”

Her efforts paid off, and the chain of events couldn’t have been more serendipitous. “You Oughta Know,” it turns out, is Dever’s go-to karaoke song. The 22-year-old actress had even used Morissette’s hair as inspiration for Amy’s look. (Dever’s representatives declined interview requests for this article.)

On the day of shooting, Wilde tossed Noah Galvin, who plays the hyper-serious theater snob George, into the scene, as he’d steadily become a comedic MVP throughout production. Morissette’s verbose lyrics aren’t easy to memorize, and Galvin had only one morning to prepare. No big deal: He’s a Broadway star who took over the title role in the popular musical “Dear Evan Hansen,” so this was familiar territory. 

“The whole afternoon felt like a ridiculous, debaucherous blur,” Galvin said. “I was given permission by Olivia and Katie to go balls out, and if someone tells me to go for it, I will go for it.” 

That included singing with his tongue hanging out of his mouth to thin his voice, telling one of George’s classmates to hush during the performance and “deep-throating” the microphone during the famous line “Would she go down on you in a theater?” (Watch an exclusive excerpt below.)

But the scene belongs to Amy, who’s watching George’s performance next to a crush (Victoria Ruesga) she’s trying to charm at the party. Amy is encouraged to take the mic, and she slowly rises and makes her way to the front of the room. The camera swirls around her, and the sound briefly fades out as if Amy is experiencing a dream, suffused in the overhead lights’ neon glow. Will she accept the call to arms? When the music snaps back into place, Amy belts the lyrics at full blast ― an introvert letting herself go despite her schoolmates’ steady gazes. Dever’s face relaxes at last, and Amy discovers her own chutzpah in real time.

“That’s something I really, really love about that scene,” Wilde said. “I wanted to put the audience into Amy’s head. I wanted to create a visceral sense of her anxiety at that moment. I wanted to point out that this is a significant moment for a character who has not yet found the strength to be courageous. For her to stand up and sing is a really huge deal, let alone in front of this crush of hers. When we shot it, I wasn’t sure exactly what we would do with the sound, but my intention was, ‘I think we’re going to warp the sound so we feel a little bit like we’re inside her head.’ But we weren’t sure exactly how we would do it. And then when we were in the sound mix, I said, ‘Can we just kind of drop it out to a ringing?’ And we watched it and everybody said, ‘Yes!’”

What we don’t see, Galvin said, is the part where scene-stealer Billie Lourd, who plays the fey druggie Gigi, joins in by licking the monocle Galvin is wearing around his neck and getting “super turned on.”

It’s a banner moment in a film full of them, and one that emblematizes the role music plays both in the movie and on its set.

Before shooting, Wilde asked Ling to create playlists that were then piped through a speaker system between takes and during the cast’s meals. Some of those songs, like Lizzo’s “Boys” and Salt-N-Pepa’s “Push It,” made it into the film. Wilde hoped to incorporate Helen Reddy’s “I Am Woman,” but she couldn’t find a good use for it. Others, like Kendrick Lamar’s “Backseat Freestyle,” proved too costly to license, according to Ling. 

A logical question one might ask is what percentage of the teen audience that seeks out “Booksmart” will know “You Oughta Know” and its power. We’re talking about a hit from 1995, after all, a time before today’s high schoolers were born. If nothing else, Wilde gets to introduce youngsters to a cultural touchstone. She wants them to know that she’s happy for them.

“I think she’s like classic rock to them now,” she said of Morissette. “Music fans do [know the song], but there’s a lot of people who are going to learn about her through this film, and that gives me great pride.”

“Booksmart” is now in theaters.