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Born Ragnar Lind in Auburn, Massachusetts, Lynn was a school teacher before he began his acting career. He came to Hollywood and made his film debut in Out Where the Stars Begin (1938). He achieved a notable success in 1938 appearing with the Lane Sisters in Four Daughters, and the popularity of the movie was so great that it was followed by three sequels, Daughters Courageous (1939), Four Wives (1939) and Four Mothers (1941) with Lynn reprising his role in each of them.

After the success of Four Daughters, Lynn was screen tested for the role of Ashley Wilkes in Gone with the Wind (1939). He was considered to be the front runner for the role based on the quality of his test, and his physical resemblance to the character as written. Lynn was used extensively during the "Search for Scarlett" playing Ashley in the screen tests for many of the actresses who tried out for the part. Eventually David O. Selznick grew worried about giving such an important role to such an inexperienced actor, and cast the more experienced and popular Leslie Howard, despite maintaining that Lynn was artistically a better choice.

Instead, Lynn acted in The Roaring Twenties, a gangster film that reunited him with Four Daughters star Priscilla Lane, as well as Humphrey Bogart and James Cagney. As one of a trio of friends, and the only one not to "go bad", Lynn won excellent reviews. His success continued with such films as The Fighting 69th (1940) in which he portrayed poet-soldier Joyce Kilmer, It All Came True (1940), All This and Heaven Too (1940) and Million Dollar Baby (1941). His movie career was interrupted by service during World War II and when he returned to the screen in 1948 he was not able to establish himself again. He was in the notably successful A Letter to Three Wives (1949) but his film career had stalled. It was not until the 1960s that he achieved more successes with BUtterfield 8 (1960) and Tony Rome (1967).

He began appearing in television, in such series as Robert Montgomery Presents, Your Show of Shows and Lux Video Theatre during the early fifties. He also made appearances on Broadway in the shows Lo and Behold! (1952), Any Wednesday (1966) and Dinner at Eight (1967). His final acting appearance was in a guest role in Murder, She Wrote in 1987, which was in fact a sequel to the film Strange Bargain (1949) and which co-starred his original co-star, Martha Scott.

After his acting career went into decline, particularly in the 1950s, Lynn began working in real estate and from then his acting career was a secondary interest.

He died in Burbank, California aged 86 from natural causes.