It's 1981 and TV producer Chuck Barris (SAM ROCKWELL) is holed up inside a NY hotel, apparently suffering from a mental breakdown. Terrified and ashamed of everything in his life, he decides the solution might be to record what he deems to have been a wasted life.
Through a series of flashbacks, we then follow him from 1955 New York where he's introduced to the world of TV production to 1961 Philadelphia where he's trying to make a pilot. It's there that he meets the free-spirited Penny (DREW BARRYMORE) who gives him the idea for "The Dating Game."
He also meets Jim Byrd (GEORGE CLOONEY), a CIA recruiter who believes Chuck fits the profile to be a freelance assassin. Although initially reluctant, Barris eventually agrees and then goes on to become quite proficient in the field, all while using his chaperone duties on "The Dating Game" as his cover for his hits.
Yet, he longs to be just a TV producer, but his interaction with shady operatives such as Patricia Watson (JULIA ROBERTS) and Keeler (RUTGER HAUER) eventually means that he's in too deep to simply walk away. From that point on, he tries to balance his TV work, his relationship with Penny and the fact that he might be the next target of an anonymous but deadly mole.