Pennyweight (1999)

Blaine Kinney, an aspiring young filmmaker, approaches an eccentric and extremely wealthy businessman, Fentworth Pennyweight III, for help in financing his first film. To his surprise, Mr. Pennyweight agrees to fund the entire movie with one small stipulation: Blaine must wear a ridiculously large and effeminate pair of earrings for exactly one year. Desperate for money, he agrees to the deal.