Greta Gerwig Sent Justin Timberlake an Impassioned Letter to Use “Cry Me a River” in Lady Bird

Greta Gerwig’s extremely well-reviewed new film, Lady Bird, centers on a group of high-school seniors as they journey through the 2002-2003 school year. Music and pop culture plays an integral role throughout in “setting the scene”, as it were, and Gerwig’s choices for the songs that play in various key moments are almost always pitch-perfect (Dave Matthews Band’s “Crash into Me” figures prominently in the narrative–and, as an aside, will be stuck in your head for days after seeing the film).

And there is one especially shimmering music cue, that takes place during a high-school party scene, a pivotal moment in the film when our protagonist (played by Saoirse Ronan) makes her move on bad boy Kyle (Timothée Chalamet) at the most popular girl in school’s pool party. And what better song to be playing at the most popular girl in school’s pool party in 2002 than Justin Timberlake’s classic pop jam “Cry Me a River”?

In order to get the rights to the song–which, lest we forget, Timberlake wrote about his breakup with Britney Spears–Gerwig wrote him a letter in order to ask for his permission. On Monday night’s Late Night with Seth Meyers, Gerwig shared the letter she sent Timberlake–and it’s delightful from start (where she addresses him as “Mr. Timberlake”) to finish (where she signs off “Your very sincere fan, Greta Gerwig”).

The opening lines grab you immediately: “I mean, what can I say? You’re Justin Timberlake. You were the soundtrack to my adolescence. Your rise corresponded exactly with my very awkward puberty”. She calls the song “sultry and sullen and infectious”, comparing it to “Gimme Shelter”. Also amusing are the places in the note where Gerwig decides to underline: the word “owned” in the sentence “Your album Justified was that year, and it owned that year”; the words “full on make out” in “She finds him ready by the pool, and she gets her wish when they full on make out”; etc.

Gerwig’s letter did the trick–and perhaps teaches us the lesson to dream big, ask for what we want, and judiciously underline to make our case.

Vanity Fair