In the fall of 1959, Darin played "Honeyboy Jones" in an early episode of Jackie Cooper's CBS military sitcom/drama, Hennesey set in San Diego, California. In 1960, he appeared twice as himself in NBC's short-lived crime drama Dan Raven, starring Skip Homeier and set on the Sunset Strip of West Hollywood. In the same year, he was the only actor ever to have been signed to five major Hollywood film studios. He wrote music for several films in which he appeared.  His first major film, Come September (1961), was a teenager-oriented romantic comedy with Rock Hudson and Gina Lollobrigida and featuring 18-year-old actress Sandra Dee. They first met during the production of the film, fell in love, and got married soon afterwards. Dee gave birth to a son, Dodd Mitchell Darin (also known as Morgan Mitchell) on December 16, 1961. Dee and Darin made a few films together with moderate success. They divorced in 1967.  In 1961 he starred in Too Late Blues, John Cassavetes' first film for a major Hollywood studio, as a struggling jazz musician. Writing in 2012, Los Angeles Times critic Dennis Lim observed that Darin was "a surprise in his first nonsinging role, willing to appear both arrogant and weak."  In 1962, Darin won the Golden Globe Award for "New Star of the Year - Actor" for his role in Come September. The following year he was nominated for the Golden Globe Award for "Best Performance by an Actor in a Motion Picture - Drama" (Best actor) in Pressure Point.  In 1963, he was nominated for an Academy Award for Best Supporting Actor for his role as a shell-shocked soldier in Captain Newman, M.D.. At the Cannes Film Festival he won the French Film Critics Award for best actor.  In October 1964, he appeared as a wounded ex-convict who is befriended by an orphan girl in "The John Gillman Story" episode of NBC's Wagon Train western television series.

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