5. Raging Bull, 1980
IMDB Rating: 8.3
This could be one of the best character driven movies in Scorsese’s arsenal. Based off a true story, De Niro went on to win his second Oscar with his performance as ex-boxer, Jake LaMotta.
Before directing the film Scorsese was actually hospitalized due to a cocaine overdose. De Niro went to see him in the hospital and convinced him it would be good to go forward with this film. The two worked on the script together for a long time as De Niro kept Scorsese sober and it turned out to be one of his best films.