Jackson, a young Los Angeles thespian, has faced rejection at every turn both as an actor and as the writer of his first screenplay. Although his best friends Chris and Disco have always managed to put a positive spin on his failures, it isn't until he meets Amy that things begin to turn around. As a young up and comer in the industry, she is the one woman who can make both of his artistic endeavors a reality. Jackson is then caught between a desire to succeed... and a desire to take care of the one person who has truly taken care of him. CONVINCING CLOONEY is a movie about not just making it, but the unpredictable road taken to get there.