77. Luke Wilson and Drew Barrymore

Drew Barrymore has lived her life in the limelight. She gained her celebrity status at a young age after starring in Steven Spielberg’s iconic ET: the Extra-Terrestrial. Barrymore is also widely recognized for her comedy films, particularly a string of movies she did with Adam Sandler. These include The Wedding Singer, Blender, and 50 First Dates, the first of which received such a degree of commercial success that it opened several other opportunities for the young actress.

In 1998, just after filming The Wedding Singer, Barrymore starred in the rom-com film, Home Fries. This is where she co-starred alongside her former boyfriend Luke Wilson. The director of the film, Dean Parisot, hit the jackpot with this duo for their apparent chemistry. He even went out to say that he saw the couple falling even deeper in love as they look into each other’s eyes during filming some of the scenes of the movie. Wilson and Barrymore were in a relationship for two years.