I think both The Hustler and The Color of Money examined the matter of self-respect as it pertains to hustling with great skill.
The Hustler
Though entusiastic to go on the road, Eddie clearly was not comfortable in the role of a predator. After his big score during Kentucky Derby week at the home of a wealthy man, the man he'd beaten said "we'll do it again sometime" and Eddie's sarcastic reply was "yeah, sure." Eddie had clearly lost some of his self-respect. He would gain it back by beating Minnesota Fats fair and square, but in the aftermath of the win, Eddie got one last dose of Burt's predatory style.
The Color of Money
Vincent was uncomfortable and repulsed by the idea of the predatory action that Eddie forced upon him. He wanted to win fair and square, as was made evident in his gambling session with Grady Seasons, when Vincent requested that Grady no longer spot him. Eddie pushed and pushed, and, ultimately, Vincent came to terms with hustling and its moral implicaitons. It all came to a head in Atlantic City, however, where Vincent dumped and bet the other side, even in his tournament match against Eddie. Now it was Eddie who was repulsed by Vincent's use of the tricks he'd taught him. Eddie had been transformed from one who endorsed dumping for profit to one who couldn't deal with it. In the world of hustiling, both Vincent and Eddie found that it's sometimes hard to look yourself in the mirror. By the end of the movie, Eddie was the one who wanted to win fair and square .... over Vincent!
The lessons of these two movies extend far beond pool, for those who cheat to accomplish anything have to live with themselves and will often be challenged to retain their self-respect.