I liked the book Wiseguy better than the movie actually, there was alot of stuff the movie didn't tell us like about Henry Hill's Military service.
Also, the movie only touched a little on his time in prison. He got away with a lot more inside than just selling some drugs.
NPR interview with 'Wiseguy' author, Nicholas Pileggi:
On how Henry dealt with his frequent prison sentences
"There are religious furloughs where you go out for religious training. It allows you to get out of the program and have contact with your family. ... Henry sees this and he says, 'Get me a religious guy.' So they got a phony rabbi to write the letter to the prison. The prison is very responsive to religious letters. All of a sudden, Henry is now going off on 'religious studies' on weekends.
"He got Jimmy Burke to pick him up, they'd cross Pennsylvania, go to Atlantic City, he'd belly up to the craps table and shoot craps until his ankles swolled. And that's what he would do for his whole religious weekend. Then get back in the car Sunday night and drive back to the prison. At the same time, his wife would fly down from New York and other wiseguys would come down and their weekends in prison were spent in Atlantic City."