While modeling, Hamilton also began taking acting classes in an effort to expand his career. His first major roles was as Samson in the 1984 television film Samson and Delilah. Later that year, producers of the crime drama series Cover Up offered Hamilton the leading role after the series' previous star, Jon-Erik Hexum, died after an on-set accident in October 1984. Hamilton had known Hexum having previously met him at an acting class when they both lived in New York. They shared the same acting coach and also competed for the same roles (both were up for the role in Samson and Delilah which Hamilton won). Hamilton initially had misgivings about taking the role but ultimately accepted it. Hamilton's first episode aired on 24 November 1984. After Hexum's death, the series struggled in the ratings. CBS canceled Cover Up the following year. After the cancellation of Cover Up, Hamilton was in talks to replace Roger Moore as the new James Bond in the 007 film series. Bond Producer Albert R. Broccoli was reportedly hesitant to cast Hamilton as the womanizing James Bond because, in real life, Hamilton was gay. Timothy Dalton was ultimately cast as James Bond. In 1986, Hamilton had a small role in the comedy film Jumpin' Jack Flash starring Whoopi Goldberg. He also guest starred on several television series including The Hitchhiker, The New Twilight Zone, The Charmings, and L.A. Law.