Man About Town (2006)

In this movie, Ben Affleck shows he has a convincingly knack for comedy. He plays Jack Giamoro, who is heading a big agency for writers and actors in Hollywood. He is married to a beautiful woman (Nina, played by Rebecca Romijn) and takes care of his father, who needs attendance, suffering from a stroke. Jack secretly attends a course in writing journals in order to get grips with his life. The movie starts with Nina confessing that she has been unfaithful to him. Jack cannot cope with this, especially when he hears that she did it with one of his clients. He throws her out of the house and threatens to end the contract with his client, a very, very successful comedy writer and very important to the agency. What follows is the world of Jack falling apart, his colleagues and friends taking different sides. A rejected Chinese screenwriter tries to get back at him by exposing the fraudulent basis on which the agency is founded. A burglary, a really horrendous but very funny dental job, John Cleese making easy money as a teacher and an audition of 'Basic Instinct'. It's all there and more. This movie is at times funny, hilarious, touching but all the time convincing and engaging. I loved it. If you had your doubts about Ben's comedic skills, see this flick. You won't regret it.