Photo: Georges Biard / Wikimedia Commons (CC BY-SA 3.0)
David Fincher's 2010 drama tells the story of Facebook's founding, and Timberlake plays Napster co-founder Sean Parker — the charismatic Silicon Valley figure who steers Mark Zuckerberg toward scale-at-all-costs ambition. It was a casting choice that surprised many at the time.
The performance proved Timberlake could hold his own in a serious ensemble, and the film went on to win three Academy Awards, including Best Adapted Screenplay. For the singer, it marked his arrival as a legitimate film actor beyond his pop-star image.