... each one featuring the word Gamble, Gambler, or Gambling in their titles!

The two Gambling Ship films were in fact two different movies: the Cary Grant version came out in 1933, and the one starring Robert Wilcox was released
in 1938... and your eyes did not deceive you - Barbara Stanwyck made two different-but-similarly-titled movies called The Lady Gambles with Robert Preston
(1949) and Gambling Lady with Joel McCrae (1934) - go figure!