I read about a hollywood movie where the plot goes on similar to this.
A person takes different roles (pilot, banker, etc., ) and cheats continuously but escapes most of the time. He starts cheating at a very early stage. Disguises most of the times in many different roles yet no one to identify him.
blah blah blah (A women comes in his life.) blah blah blah
Finally he gets caught and ends up in a prison. The inspector (who was following him and who caught him) finally helps him release....
Also remember that the lead role has a sister.
Definitely a hollywood film but having a doubt if the lead role was played by Tom Cruise
I also remember this movie in Imdb has a good rating too but I am not getting the movie name.