Spears's first public relationship was with fellow Mickey Mouse Club member (and star in his own right) Justin Timberlake. Timberlake is himself an actor (The Social Network), but we choose Andrew Garfield for his lanky charm. What's more difficult than encapsulating Timberlake's affable personality, though, is pulling off his distinctly early ‘00s frosted tips and all denim look. We think Garfield is up for the task. 

Jason Alexander may have been Spears' shortest-lived lover—they were married for only 55 hours—but he's entered an indelible place in our collective memory. (Well, some of ours.) RJ Mitte, best known his role in Breaking Bad, fits the bill. As Walter "Flynn" White Jr. he was both comic and serious, and we imagine he'd lend an air of sincerity to this fleeting romance. 

Spears and Kevin Federline's high-profile marriage (and divorce) defined pop culture of the ‘00s. We thought Aaron Taylor Johnson, with his rakish good looks, would be a good fit for the former dancer, rapper, and all-around bad-boy. The true task will be evolving from a young "K Fed" to Kevin Federline, a divorced father of two. 

It's unclear how much of a role Jamie Lynn Spears will play in Britney, but who could forget Spears' precocious little sister? We choose Abigail Breslin for the role. We can picture her as the teen eagerly following in her older sister's footsteps, eventually landing a starring role in her own Nickelodeon television series, Zoey 101.