Notes on the You Oughta Know Scene in Booksmart

These days everywhere I, forty (one) year old man, go, I see young women who were probably barely alive when I was teenager, if they were alive at all, dressed like Alicia Silverstone in Aerosmith’s “Cryin’” video. You know what I’m talking about Gen Xers: the red flannel, the boot cut jeans, the combat boots. This is not a new observation, of course. Fashion, like everything, is cyclical and so every generation experiences it. One of my senior photos from the mid-90s involved wearing a polyester shirt and striking the “Saturday Night Fever” pose. But that makes it no less weird when it’s your generation’s turn. And what makes copying Alicia’s look weirder is that Alicia’s look was deliberate disinterest – it declared: “I don’t care how I look.” For Gen X, it wasn’t cool to care, see. That’s why in the video she reeled in Stephen Dorff by making him care and then shoved that care right back in his face with the bungee jump fake-out concluding with the most memorable middle finger in the history of the world.

I tried to act like I didn’t care in the mid-90s but it never really took. That’s why when I arrived a few seconds late to Mr. Calvert’s sociology class knowing full well that his rules dictated showing up after the bell meant a detention, I didn’t challenge his rules by coolly acting apathetic toward them but dutifully showed up for detention the next morning. And that’s why I loved Alanis Morissette. Oh, Alanis was ironic too, sure, of course, which is why her biggest hit was literally called “Ironic”, a song constantly cited my pseudo-observationalists (sic) for not really being ironic at all which, of course, duh, is ironic. But her first hit, “You Oughta Know”, released in the summer before my senior year, an Alternative “You’re So Vain” fiery screed against an ex, was earnest, vehemently so, not ironic. I had no exes, mind you, to hold grudges against because I had no exes at all, but I sort of semi-innately grasped that I preferred being earnest to ironic and I cherished the blood-in-the-mouth earnestness of “You Oughta Know.”

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“10 Things I Hate About You” was released at the tail-end of the late 90s teen movie boom. And though in his disaffected air Heath Ledger’s Patrick Verona seemed to emerge straight from the Seattle (where the movie was set) grunge scene, when it came time for his character to declare romantic affection for Julia Stiles’s Kat Stratford by publicly serenading her he did so not by singing a song of the era but by reaching back, all the way to 1967 and Frankie Valli’s “Can’t Take My Eyes Off You.”

I heard “Can’t Take My Eyes Off You” frequently on KIOA, the Des Moines, Iowa oldies station, which is what me and my best pals Jacob and Kris were often tuned into while riding around in Kris’s car with no real point or purpose, through the quasi-mean streets of West Des Moines or along scenically rural Highway 6 toward Adel and then possibly north to Panora, where Kris’s parents had a lake house where we would listen to more KIOA while playing ping pong in the basement. One summer night – and I hesitate to divulge this information – the three of us were up way too late and kept calling in to the poor late night D.J. requesting songs which led to him playing a Billy Joe Royal tune of his own accord and then instructing us to call back in after the song was over to discuss it which we did because we were hella cool. KIOA was a constant, joyful companion.

“There Goes My Baby” by The Drifters. “Be My Baby” by The Ronettes. “Back in My Arms Again” by The Supremes. These were, and remain, some of my favorite songs of all-time. These were not songs I loved ironically. These were songs I loved as much as “Check the Rhime” by A Tribe Called Quest, “Creep” by TLC, and “Leaving Las Vegas” by Sheryl Crow. I was falling in love with the same music my parents fell in love with when the music was brand new, which wasn’t bad or troubling, just disorienting, at least for them.

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One of the most delightful moments of Olivia Wilde’s “Booksmart” finds one of her co-protagonists, Amy (Kaitlyn Dever) at a night-before-graduation party being forced by the girl on whom she’s crushing into performing “You Oughta Know” karaoke, an interesting song choice given it’s a quarter-century old. Wilde is apparently a fan of Alanis’s hit and, per the HuffPost, wrote a letter to Morissette hoping to acquire the rights which, obviously, were granted. In the letter, Wilde gushed about what the song meant to her, and at the end of the article she spoke about introducing the song to a whole new generation. To that point, I have encountered scuttlebutt, mostly in the is-this-real-life-or-not environs of Twitter that have questioned the song choice and how it differs from, say, 2017’s “Lady Bird” which employed an actual song (“Crash” by Dave Matthews Band) of the actual time (2002) for its big musical moment.

But in the same HuffPost article Dever cited “You Oughta Know” as her karaoke song, suggesting it already has trickled down to today’s youth, which is precisely why I, aging Gen Xer, who used to rock out to “You Oughta Know” in his car on the tape that I recorded it to from CD, found this scene as disorienting as I did moving. It’s as if I was suddenly transported back to the house I grew up in but not as myself, no, but merely an impartial observer, watching my parents watch youthful me, seeing what it was finally like for them to see their son singing along to KIOA, the passage of time laid bare even as it simultaneously blurred all lines.