Weiss was an associate of renowned producer Hal B. Wallis, whose credits included The Maltese Falcon (1941), Casablanca (1942) and several films starring Martin and Jerry Lewis. The writer was present when Wallis, then based at Paramount Pictures, made Presley's screen test in March 1956. Weiss provided the story for Presley's Blue Hawaii (1961) and wrote or co-wrote the screenplays for the films Girls! Girls! Girls! (1962), Fun in Acapulco (1963), Roustabout (1964), Paradise, Hawaiian Style (1966) and Easy Come, Easy Go (1967).
