The Ballad(s) of Justin and Britney, Vol. 1: ‘Cry Me a River’

Sydney Urbanek
16 min readMar 19, 2020

“The bridges were burned / Now it’s your turn, to cry”

On “The All-New Mickey Mouse Club” (MMC)

This essay is the first of a two-part series on the music videos that came out of the Justin Timberlake/Britney Spears breakup. (Click here to read “The Ballad(s) of Justin and Britney, Vol. 2: ‘Everytime.’”)

2007 was particularly good to Justin Timberlake. He spent most of the year touring in support of his second studio album, FutureSex/LoveSounds, which spawned four number-one singles — “SexyBack, “My Love,” “What Goes Around… Comes Around,” and “Summer Love” — and ultimately won him as many Grammys. By the time he sat down with Oprah Winfrey on her namesake show in September, he’d also appeared on the TIME 100, aired his tour as an HBO special, starred in Shrek the Third, and won an Emmy for “Dick in a Box.” In the Oprah Winfrey Show episode that aired on September 19, Oprah asks Justin about staying grounded, the necessity of hard work, and how he’d been “living that celebrity life” — Oprah’s words, not his — since he was on The All-New Mickey Mouse Club (MMC) in his preteens. But there was an elephant in the room: 2007 had not been so good to fellow Mouseketeer Britney Spears, whom Justin had dated from roughly 1999 to 2002.

“I wouldn’t be doing my job if I didn’t ask the Britney question,” Oprah says.

“What question is that?” Justin responds amid audience giggles.

“What do you think is going on with Britney?”

On “The Oprah Winfrey Show” in September, 2007

Justin firstly tells Oprah that he doesn’t really know, and it’s worth noting right off the bat that, for all our speculating at the time, none of us actually did. Coverage of Britney’s so-called breakdown in 2007 was not only severely lacking in compassion, as Roslyn Talusan argued for Flare last year, but also missing crucial context. Retellings don’t tend to include, for example, that Britney’s aunt had died just weeks before the infamous head-shaving incident in February, or that she thereafter described that night as “a little bit of rebellion” — framing pretty different from “THE NIGHT BRIT CRACKED.” A week and a half before Justin’s Oprah interview…

Sydney Urbanek

Writer on mostly pop music x moving images. Often at