It's uncommon that someone can say that he worked with more than one of the actors that portrayed James Bond in film, but Clifton James is one of the few who can make such a claim. James began acting during the 1950s in small roles on such programs as "The Phil Silvers Show," "Decoy," and "Naked City." He continued landing bit parts in television ("Gunsmoke") as well as motion pictures ("Cool Hand Luke") throughout the 1960s. During the 1970s James built a two-part association with the James Bond film franchise; he portrayed the humorous Sheriff J.W. Pepper in "Live and Let Die" (1973) and "The Man with the Golden Gun" (1974), appearing alongside Roger Moore. James would continue to secure roles in such popular films as "Silver Streak" and "Superman II," before appearing in the hit 1987 film "The Untouchables," which featured original Bond actor Sean Connery. James continued to add to his acting resume in the ensuing decade, but by the early 21st century, he was landing roles much more infrequently.