Bob Denver, who portrayed the clumsy yet lovable Gilligan, brought warmth and humor to the series. Born in 1935, Denver’s portrayal of the naïve first mate became a defining role in his career, culminating in his passing in 2005 at the age of 70. Alan Hale Jr. played the strong and protective Skipper, a role he embraced from 1964 until his death in 1990 at the age of 68, leaving a legacy of fatherly charm.