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Joining a cadre of future stars like Jason Segel and Seth Rogen, James Franco appeared on the short-lived (but critcially acclaimed) 1999 coming-of-age TV series Freaks and Geeks, playing "freak" Daniel, a troubled slacker in a tumultuous relationship with Kim (Busy Phillipps).
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In his Golden Globe-winning 2001 breakout role, Franco perfectly channeled the tortured – and well-coiffed – original bad boy with a heart of gold, James Dean, for the eponymous TV movie.
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Giddyap! The actor hoofed it as the tragic romantic lead in 2006's Tristan & Isolde.
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Clad in pajamas and smelling like weed, Franco had audiences in stitches as unlikely hero Saul in the 2008 stoner action-comedy, Pineapple Express.
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Franco showed off his musical side in 2009, strumming the ukulele while filming Eat, Pray, Love in New York City.
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Talk about wigging out! The actor donned a blond wig and covered his face in white powder while goofing around at a 2011 Sundance bash.
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He sure cleans up well! Franco cut an impressive figure on the red carpet at the 2011 Screen Actors Guild Awards in a simple yet chic black suit.
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Franco was nearly unrecognizable while filming Spring Breakers in March 2012, thanks to his cornrows, shades, tattoos, and, of course, those gold grills.