2. Good Will Hunting (1997)
The first major film collaboration by childhood friends Ben Affleck and Matt Damon, Good Will Hunting is one of the greatest films of all time, let alone of the 90s. Young Bostonian Will Hunting (Damon) spends his days hanging around with childhood friends Chucky (Ben Affleck) Morgan (Casey Affleck) and Billy (Cole Hauser) drinking in the Irish bars and generally causing trouble. Will is different though, he spends his working days as a janitor at MIT, and begins secretly finishing mathematics problems left by Professor Gerald Lambeau (Stellan Skarsgård). After Will and his friends get into a fight with old classmates, Will is put before a judge and sent to jail. He is only saved by Lambeau who agrees with the judge, that if Will is allowed to walk free, he will send him to a counsellor and make him his understudy at MIT. The counsellor that Will ends up seeing is Lambeau's old MIT room mate, Dr. Sean Maguire (Robin Williams), a man made tough by the death of his wife and an upbringing by an alcoholic father in south Boston. Although the film is about the relationships Will struggles to develop including the romance between him and his Harvard undergraduate love Skylar (Minnie Driver). The raw emotion comes from the conversations between Will and SeanWill and Sean connect through their love for the Boston Red Sox and their tough childhoods. Sean tells Will in a very moving scene that the abuse he suffered at the hands of his foster father is "... not your fault". http://youtu.be/92D15qtI_Gk The premise of the film coupled with a fantastic cast makes this one of the greatest films. Easily one of Damon's best performances but Robin Williams takes the top spot for his outstanding portrayal of Sean Maguire. Williams won the Academy Award for Best Supporting Actor. Damon and Affleck won the Academy Award for best screenplay. Over all the film was nominated for 9 Academy Awards. I urge everyone to watch Good Will Hunting, if only to Robin Williams in a different light.