72. Chris O’Donnell and Reese Witherspoon

Reese Witherspoon’s breakout performance was in the movie Cruel Intentions in 1999. She would then solidify her claim to fame with the movie Legally Blonde. The film’s commercial success and acclaim would also lead to a sequel and further open the gates of opportunity to the actress. In 2005, she would do her award-winning performance in the movie Walk the Line, portraying June Carter Cash. For this, an Academy Award was given to her credit.

Long before all these though, Witherspoon began her acting career during her teenage years. Her screen debut was in the film The Man in the Moon in 1991. Back in those days, she was rumored to be in a relationship with Chris O’Donnell, who was also on the rise to fame. He was known for his performance in Scent of a Woman and for portraying Dick Grayson in Batman Forever and Batman & Robin movies.