singles poster

4. Singles (1992)

Singles was Crowe’s second directorial effort and it bares the rawness of a young filmmaker still finding his voice. Of course, the Seattle-grunge based love story also does a wonderful job of capturing that time and place in popular culture thanks to a killer soundtrack that was probably more successful than the film was. But besides the music, which has been and forever will be Crowe’s calling card, Singles has a real authenticity to it. You know these people, you understand their plights, and seeing that familiarity in an alien setting is what good filmmaking is all about. A relatable story in an unrelatable world would also become a Crowe staple.

Almost Famous Poster

3. Almost Famous (2000)

I know I’m going to get some crap for this, but first let me explain. These last three films are on another level. They’re all masterpieces in their own right and having to choose between the three is a cruel punishment. On any given day any one of these next three films could be in any one of these three final spots. I love them all, maybe this one the most, but I was forced to pick and now I’ll explain why I put Almost Famous at number 3.

The Untitled cut is better. There, I said it. The theatrical cut of Almost Famous is wonderful. Magical. A personal, touching story that blends fantasy and reality with incredible music, better performances and impeccable direction. It’s a film I’ve come to love more and more every single time I’ve watched it. But then you watch the Untitled cut and it’s just a little bit better. A few of the minor, insignificant plot holes get covered up. Some of the tertiary characters are given more room to breathe, and as a result an already magnificent film gets that much better. But we’re talking about the theatrical cut of Almost Famous and, because of that distinction, it gets the ever so slight, minuscule drop off cut from the next two, equally perfect, movies.

Jerry Maguire poster

2. Jerry Maguire (1996)

Much like Almost Famous, Jerry Maguire has it all. It takes us into an unknown world and makes it incredibly interesting and accessible to all. Every emotion in your body gets stimulated at least once or twice. There are at probably five or six absolutely spot on, perfect moments that basically have defined what Cameron Crowe can be as a filmmaker. The praise just goes on and on and on. And yet, as good and even and crispy as Jerry Maguire is, it’s missing just a hint of something that places it in slot two.

Say Anything poster

1. Say Anything… (1989)

Everything I’ve said about the last two movies I can say again here. But what makes Say Anything, in my mind, Cameron Crowe’s best movie is how raw it is. It was Crowe’s first film and that he could come out and tell a love story that’s so different, yet so honest, and fill it with moments and dialogue that will last forever boggles the mind. If we’re being objective, Almost Famous and Jerry Maguire are probably more well-rounded films, but Say Anything goes for it, doesn’t apologize, and ends up being one of – if not the – best romantic comedies of all time. And it was Cameron Crowe’s first film, which makes the achievement that much more amazing.

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