I'm sure they made this TV movie to cash in on the Clint Black name, but I think it would have been a more compelling movie had the screenplay been better written, and had it starred anyone but Black. The singer/actor crossover thing almost never works (Masked and Anonymous, starring Bob Dylan, is another example of horrid crash-N-burn. And that film had lots of REAL actors).
This goes both ways. In the early 1930's, John Wayne was making "Poverty Row" westerns and they decided to make him "Singin' Sandy". I love John Wayne movies, but the poor man couldn't sing a note. They dubbed his singing with a voice so far removed from Wayne's that it was ridiculous. (Check Riders Of Destiny on Youtube for THAT little chunk of dreck. The movie starts right off with a song.) Wayne became very embarrassed when he made personal appearances and children clamored for him to sing a song. He got rid of Singin' Sandy just as fast as he could, much to the benefit of all.
Cadillac Jack deserves a good turn on screen, but Clint simply cannot act, and the screenplay is a cliché-ridden mess. It looks like a huge mistake for all involved. If, in your eyes, Clint Black can simply do no wrong, then this movie might be up your alley. For everyone else, not so much. It's not "Monster A - Go Go" bad, but it's a pretty poor film.