Pretty in Pink (1986)

Jon Cryer plays Duckie in this chapter of John Hughes' extensive chronicles of coming-of-age in suburban Chicago. Duckie is a loser who can't get up the nerve to proclaim his love for his crush of innumerable years, Andie, played by Molly Ringwald. Inevitably, he travels by bicycle. In case you might miss the bicycle=loser intent of the film, Duckie makes it perfectly clear with his quip that "Drinking and driving don't mix. That's why I ride a bike." as he leaves Andie's room, juice box in hand. He also veers close to pervert territory towards the end of the film when he stalks Andie on his bike. All this might have been redeemed by the reported original ending of the film, in which Duckie gets the girl. Alas, she ends up with the wealthy drip with the nice car.