Tobey then, in 1957, appeared in the syndicated religion anthology series Crossroads in the role of Mr. Alston in the episode "Call for Help" and as Jim Callahan in "Bandit Chief" in the syndicated western series The Sheriff of Cochise. Later that same year, Tobey starred in the television series The Whirlybirds, a successful CBS and then-syndicated adventure produced by Desilu Studios. In it he played the co-owner of a helicopter charter service, along with fellow actor Craig Hill. The Whirlybirds was a major hit in the United States and abroad, with 111 episodes filmed through 1960. It remained in syndication worldwide for many years.
In 1957, Tobey portrayed a sheriff in The Vampire (a film that some sources today often confuse with the 1935 production Mark of the Vampire). That year he also appeared in a more prestigious film, serving as a featured supporting character with John Wayne and Maureen O'Hara, the co-stars of John Ford's The Wings of Eagles. In that film, Tobey—with his naturally red hair on display in vibrant Metrocolor—portrays a highly competitive United States Army Air Service officer. In one memorable scene he has the distinction of shoving a piece of gooey cake into the face of John Wayne, whose character is a rival United States Navy aviation officer. Not surprisingly, a room-wrecking brawl ensues.