Rise to Fame
Being the son of Alan Hale Sr., who appeared in over 235 films, gave him a head start in Hollywood and about nothing else. He worked through the 1950s in Westerns and bit parts while his father's reputation loomed over him. The Skipper role on Gilligan's Island in 1964 was the break he'd been waiting for. CBS canceled the show after three seasons of modest ratings, but the reruns hit syndication almost immediately, and by the 1970s, the show was more famous dead than it ever was alive.
In the Spotlight
He reprised the Skipper in three TV movies, voiced him in two animated spinoffs, and visited kids in hospitals dressed as the Skipper for years after the show ended. Off-screen, he owned Alan Hale's Lobster Barrel restaurant on La Cienega Boulevard before reportedly being phased out of the business in 1982. He wasn't fighting his legacy. He was running it.
Side Notes
His father Alan Hale Sr. played Porthos the musketeer in a 1939 film. Alan Hale Jr. played the same character in The Fifth Musketeer in 1979, forty years apart. He served in the U.S. Coast Guard from 1942 to 1945, and the gold pinky ring he wore in virtually every scene was his father's, set with a diamond and emerald. He even wove it into the Skipper's backstory on the show, which was either a tribute or just a way to never take the thing off.
Final Chapter
After his death from thymus cancer on January 2, 1990, the U.S. Coast Guard contacted his widow Naomi to offer a full military funeral at sea in recognition of his wartime service. She declined per his wishes. His ashes were scattered in the Pacific Ocean. Dawn Wells was the only Gilligan's Island cast member present at his funeral.