16. William Page in 101 Ways (The Things a Girl Will Do to Keep Her Volvo) (2000)

Gabriel Macht played William Page in this offbeat romantic comedy that told the story of the hilarious extremes a woman would take to protect her precious car. The movie was not a box office success, but it did reveal Macht's charm and ability to make an offbeat character relatable. This indie film, with its whimsical premise, was a stepping stone for Macht as he navigated the complex Hollywood terrain. While the title of the movie is quite long, the taste that Macht gave through his performance served as a groundwork for his big performances when he portrayed Harvey Specter in Suits over a decade later.
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