When requesting a favor from Justin Timberlake, there’s only one way to begin your ask: “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.”
This prelude worked for Greta Gerwig, writer and director of Lady Bird, the indie film about a young woman’s senior year in high school, which recently became Rotten Tomatoes’ best-reviewed movie ever. Gerwig needed Timberlake’s permission to use the song “Cry Me a River” in Lady Bird. She had already written the angsty 2002 pop hit into her script.
Instead of contacting the singer through agents, Gerwig wrote him directly. She did the same with singers Alanis Morissette and Dave Matthews, whose respective hits “Hand in My Pocket” and “Crash Into Me” also feature in Lady Bird. Gerwig recently read the letters (all successful) on Late Night With Seth Meyers.
At once humorous, genuine, and slightly creepy, Gerwig’s letters, previously published in Vulture, epitomize how to reach out to your idols, be they pop stars, business tycoons, or normal people making a positive difference. Her approach mirrors the perfect qualities of a cold email, which are tailored to ensure that you not only receive a response, but also that, if you’re asking for something specific, you get what you want.
In all three letters, Gerwig opens with a personal anecdote, using visual language to evoke emotion. “The very first cassette tape I ever bought was Jagged Little Pill,” she writes to Morissette. “I would listen to ‘Perfect’ over and over in my living room, memorizing the lyrics, feeling that it was written just for me.”
She then includes honest, highly specific flattery, ensuring the recipient knows the same message was not blasted out to hundreds of other contenders. To Timberlake, she writes: “Between *NSYNC and your solo work every year of my growing up was defined by your sound. … ‘Cry Me A River’ is… sultry and sullen and infections – what ‘Gimme Shelter’ must have felt like to the kids of the late 60s. It’s a song that instantly makes you feel cool and sexy when you play it.” To Matthews, she writes that his song “Crash Into Me” was, and still is, “the most romantic song ever” (emphasis Gerwig’s).
Having caught her readers’ attention, she shifts to quick background on Lady Bird, contextualizing the songs’ importance to her heroine’s emotional development. Most importantly, she asks for something that’s easy to say yes to (the rights to use their works in her film), emphasizing their singular necessity of the requested songs. “Crash Into Me,” Gerwig tells Matthews, is used as “the turning point” when Lady Bird, the film’s protagonist, ”comes into her own, declares her love for the song and what she actually cares about [in] life. It is impossible for me to imagine this movie without it.”
Closing the letters, Gerwig thanks the recipients for their time and consideration. She then includes a final emotional appeal, again emphasizing the profound impact their work had on her life and art. “Thank you for making all the music you did. You made a lot of girls feel like they could do anything,” she tells Morissette.
Beyond educative value, Gerwig’s letters provide a healthy dose of nostalgic happiness. You can read them in full below.