The Basketball Diaries

So you're telling me that in the grand arena of 'Greatest Leonardo DiCaprio Movies of All Time,' 'The Basketball Diaries' doesn't just show up to play, it schools the competition. This film is DiCaprio in his rawest form—before the iceberg, before the bear, just Leo and a basketball, diving deep into the gritty underworld of teenage angst. Fans are like, 'Remember when Leo was just a messed-up kid on the court?' It’s the ultimate underdog story, but with more sweat and tears. You can’t talk Leo without it; it’s like ignoring the first chapter of a legend!