The Oklahoma Kid

Later on the evening before the 1893 Oklahoma land rush, James Cagney (title character) enters the saloon throwing around money he stole from McCord (Humphrey Bogart), who stole it himself, and who sends his goons (Edward Pawley, and Ward Bond as “Handley”) to inquire, in Warner Bros.’ The Oklahoma Kid , 1939.

In Oklahoma, 1893, eve of the Cherokee Strip Land Run, James Cagney appears, an as-yet un-named and unaffiliated cowboy, introducing himself to Rosemary Lane, daughter of the judge (Donald Crisp), annoying Ned (Harvey Stephens) then tangling with the innkeeper (Irving Bacon), early in the Warner Bros. Western The Oklahoma Kid, 1939.

It's James Cagney vs. Humphrey Bogart...in the Old West! in The Oklahoma Kid (1939).