He is best remembered for his many character roles, in particular as a frequent sidekick of Errol Flynn, as well as films supporting Lon Chaney, Wallace Beery, Douglas Fairbanks, James Cagney, Clark Gable, Cary Grant, Humphrey Bogart, and Ronald Reagan.

[1] His son, Alan Hale Jr., also became an actor and remains most famous for playing "the Skipper" on the television series Gilligan's Island.

He became a leading man while working in 1913–1915 for the Biograph Company in their special feature film productions sponsored and controlled by Marc Klaw and Abraham Erlanger.

His other films include the epic The Trap (1922) with Lon Chaney, Skyscraper (1928); as well as Fog Over Frisco with Bette Davis; Miss Fane's Baby Is Stolen with Baby LeRoy and William Frawley; The Little Minister with Katharine Hepburn; and It Happened One Night with Clark Gable and Claudette Colbert; (all released in 1934); Stella Dallas with Barbara Stanwyck; High, Wide, and Handsome (both 1937) with Irene Dunne and Dorothy Lamour; The Fighting 69th with James Cagney and Pat O'Brien; They Drive By Night with George Raft and Humphrey Bogart; Virginia City (all 1940) with Errol Flynn, Randolph Scott, and Humphrey Bogart; Manpower (1941) with Edward G. Robinson, Marlene Dietrich, and George Raft; and as the cantankerous Sgt.

[3][4][5] Hale's wife of over 30 years was Gretchen Hartman (1897–1979), a former child actress, silent film player, and mother of the couple's three children.