Greta Gerwig’s spellbinding directorial debut Lady Bird is quasi-autobiographical. Between the fall of 2002 and the fall of 2003, as far as we’re aware, Gerwig didn’t spend a lot of time throwing herself out of moving cars after crying to the Grapes of Wrath audiobook. But she did bump the heck out of Justin Timberlake’s debut studio album Justified. Evidence comes in the form of an adorable letter she wrote to “Mr. Timberlake” to procure the film rights to his iconic Britney Spears-inspired breakup ballad “Cry Me a River.” Gerwig sent some equally amazing fan mail to Alanis Morissette and Dave Matthews, as she revealed on Late Night With Seth Meyers. Morissette’s “Hand in My Pocket” and Matthews’s “Crash Into Me” also feature on Lady Bird’s charmingly 2000s soundtrack.
“I remember being in the cafeteria and someone played it to me on their Discman and I wanted to hear it again, right away, and as loud as possible,” Gerwig wrote of “Cry Me a River” in her J.T. letter. “Immediately after school I went to the Tower Records and bought both the CD and the cassette tape because my car didn’t have a CD player.” She described the song as “sultry and sullen and infectious — what ‘Gimme Shelter’ must have felt like to kids of the late 60s…. It transmits the cool.”
Gerwig’s letter to Morissette reveals that she saw the film Dogma because she heard that the artist played God, “which seemed totally fitting to me.” To Matthews, she recalls making her Dad take her to see Dave Matthews Band play in Sacramento, Lady Bird’s divisive setting and Gerwig’s own hometown. Obviously, all three of teenage Gerwig’s 2000s heroes were charmed by her enviable penpalling skills. “Crash Into Me” features in Lady Bird twice, including one of the coming-of-age saga’s most pivotal and poignant scenes. Check out the letters below, via Vulture.