Liam Clancy, Ramblin', Gamblin' Willie. Lonely Heartstring version. Dylan's version. Dylan borrowed the melody from Brennan on the Moor.
The Band, Up on Cripple Creek
Kenny Rogers, The Gambler
Barrett Strong, Money. Flying Lizards' parody.
Allman Bros., Ramblin' Man
B. B. King, Gambler's Blues
Blood, Sweat and Tears, Go Down Gambling
Buckwheat Zydeco, Jackpot
Ry Cooder, I Got Mine. Frank Stokes' 1928 version.
Ramblin' Jack Elliot, Roving Gambler. A later version from his Kerouac's Last Dream album.
Dolly Parton, Silver Dagger. Great version, but then so is Joan Baez's.
John Cohen/Down Hill Strugglers, The Roving Gambler
Tex Ritter, The Deck of Cards, 1948. They don't make 'em like this anymore.