Mr. Deeds: Jean Arthur (1936) vs. Winona Ryder (2002)
Character: Babe Bennett
Adam Sandler's 2002 fish-out-of-water comedy Mr. Deeds was a remake of 1936's Mr. Deeds Goes to Town. And, fortunately, both incarnations of the story had a beautiful female lead.
Jean Arthur was radiant, no doubt, but, much like everything else she's pocketed over the years, Winona Ryder stole our heart years ago, and she's yet to give it back. Thankfully for her, we're not pressing charges.
Winner: Winona Ryder