18. Jim's Encounter With His Mother - The Basketball Diaries
This is one of Leonardo DiCaprio's earlier films, coming out two years after he was nominated for an Oscar for his work in What's Eating Gilbert Grape, but two years before he became a superstar with Titanic. The Basketball Diaries is about a group of kids in Boston who are growing up on the wrong side of the tracks and starting to make some really serious mistakes in terms of heavy drug use. The most difficult scene to watch is when Leonardo DiCaprio goes home strung out on heroin only to discover that his mother has locked him out; she's had enough of his behaviour, and is attempting to show him tough love. He sits outside the door, begging to be let in, while his mother sits on the other side, crying. It showcases the darkest depths of drug addiction, and it's especially painful for everyone who has children. You don't have a heart if Leo doesn't kill you with his "I'll be a good boy" line.