Webb was born in Denver in 1909 and graduated from Stanford University in 1930. He became a fiction writer for national magazines, including Collier's: The National Weekly, Cosmopolitan, and The Saturday Evening Post, in 1936 and a screenwriter two years later.
Webb's early screenplays were written for Republic Pictures. He did a series of films starring Roy Rogers and directed by Joseph Kane: Nevada City (1941), Bad Man of Deadwood (1941), Jesse James at Bay (1941) and South of Santa Fe (1942) with Roy Rogers. He also did Rags to Riches (1941) directed by Kane.
Webb was commissioned an army officer in June 1942 and became a personal aide to General Lloyd R. Fredendall who was commander of the II Corps. Webb accompanied Fredendall to England in October 1942 and participated in the invasion of North Africa in November 1942 when the Second Corps captured the city of Oran. The Second Corps then attacked eastward into Tunisia. In February 1943 the German army launched a counterattack at Kasserine Pass which repulsed the Second Corps and nearly broke through the Allied lines. The Supreme Commander Dwight D. Eisenhower relieved Fredendall of command in March 1943 and sent him back to the United States where he became deputy commander of the Second United States Army at Memphis, Tennessee.

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