9. The Graduate (1967)
In 1967, Dustin Hoffman had his breakout role as Benjamin Braddock in Mike Nichols' treatise on disillusionment, The Graduate. Fresh out of college with no plans for his future, Ben decides to start an affair with a friend of his parents. Things get... well, weird... when Ben takes Mrs. Robinson's daughter Elaine out on a date. Although he takes her to a place so sleazy that Elaine ends up with tassels bring flung in her face and crying, Ben schmoozes his way back into her heart and scores a second date. But before he can take Elaine out again, Mrs. Robinson strong-arms Ben into confessing to Elaine about the affair. She leaves for college, but Ben is dead-set on marrying her despite having gone on just one date. When Elaine is later at the altar with someone else, Ben storms into the church, pounding on the walls and screaming "ELAINE!" at the top of his lungs. She ultimately leaves with Ben after awkwardly screaming herself, and the two share an uncomfortable ride in the back of a bus. So this Valentine's day, don't be mad at your man for buying white flowers instead of pink; instead, be glad he didn't sleep with your mother and publicly embarrass you at your wedding.