The Evolution of Justin Timberlake, Thespian Image via Make A GIF

Longshot (2001)

Role: Valet

As if he realizes what a horrible movie Longshot is (the movie was only made to promote Lou Pearlman's bands, i.e. 'N Sync, O-Town, and LFO), Timberlake also gives a horrible performance as an incompetent, yet bad boy valet. 

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