4. “Cry Me a River” by Justin Timberlake
When Greta Gerwig wrote Justin Timberlake a letter to ask if she could use “Cry Me a River” in her directorial debut “Lady Bird,” she aptly described the track as “sultry and sullen and infectious — what ‘Gimme Shelter’ must have felt like to the kids of the late ’60s.”
Gerwig was 19 when “Cry Me a River” was released, just a few years younger than Timberlake was when the song was written — or, more accurately, when it came spilling out after a heated phone call with his then-girlfriend.
As producer Timbaland recounted in 2011: “I was like, ‘Man, don’t worry about it,’ and he was like, ‘I can’t believe she did that to me’ and he was like, ‘You were my sun, you were my earth…’”
Against all odds, Timbaland makes Timberlake’s angst and spite sound impossibly stylish, draping his famous falsetto with streaks of rain, layers of beatboxing, and Gregorian chants.
While that hardly sounds like a winning formula, “Cry Me a River” succeeds precisely because it’s not bound by common laws of etiquette and chill. If most breakup songs are like sitcom episodes, “Cry Me a River” is the vengeance plot on a soap opera.