Tom Cruise’s Greatest Film?

As this weekend approaches and Tom Cruise’s latest film American Made hits theaters, I’m left thinking about Cruise’s overall career. Originally, I was planning on making a list of some of my favorite Tom Cruise films but as I was preparing for this, I realized that there was only one film I wanted to discuss.


Having a favorite Tom Cruise movie is like having a favorite Beatle. Some say they like John or Paul, while I always liked George. It all depends on the individual. When the conversation of favorite Tom Cruise movies come up, often such films as Top Gun, A Few Good Men, or Jerry Maguire are mentioned. I’m not here to say that any of those are wrong. I enjoy all of those movies. A Tom Cruise movie is like a slice a pizza, no matter how bad it is, at the end of the day, it’s still pizza and pizza is great. What I am here today to do though, is give some love to a film that I don’t feel gets the appreciation that it deserves.

Coming out in 2001, the Cameron Crowe directed remake mostly came and went. With moderate success at the box office, only a Golden Globe nomination for Cameron Diaz, and an Oscar nomination for a Paul McCartney song that shared the same name as the film, it makes sense that not many people talk about the movie. I, however, believe that much like a good $10 bottle of wine, time is its best friend. Going back and watching a film like Top Gun, while fun, is mostly fun because of how cheesy and dated it is now. The beach volleyball scene alone is enough for a good laugh. In my opinion, Vanilla Sky is timeless.


The film touches on so many different elements of life: not being respected by your peers, falling in love, living with mistakes and the regret and pain that those mistakes cause, and finally, death. The film opens, much like it ends, in a dream-like state. It’s at this point, even if you don’t know where the film is going, that, as an audience member, you’re left questioning what’s going on. From the beginning, this movie tells you to think about what you’re seeing. Every scene is important.

There’s no need to break this movie down scene by scene, but once the movie gets underway and it gets the audience’s attention, that’s when, one by one, great performance after great performance begin to be brought to light. Cruise is, of course, phenomenal in this film. Especially when you consider the fact that he delivers most of his performance behind a mask and a rather large facial prosthetic. It would have been easy for Cruise to get lost in all the makeup and props but he never loses control. Even when his face is completely covered, he’s able to deliver an emotional performance.


I think what makes this performance seem even more impressive is the fact that the film starts by showing us Tom Cruise playing Tom Cruise. There’s a quick hint that there’s something more going on with his character as the film cuts to a scene between Cruise and the always awesome Kurt Russell, but it quickly cuts back to Cruise at his most… Cruise. He’s the coolest guy in the room and every woman in that room has either slept with him or is waiting in line to be the next. By making us think we’re just going to get a boring Tom being Tom performance for the first few minutes of the movie, it makes the journey that the character goes on even more incredible and proves that the sweet is never as sweet without the sour.

On top of Tom’s amazing performance, the film gives us Cameron Diaz delivering one of her best performances of her career where she plays a crazed woman that has fallen in love with Tom’s character. What’s great about Diaz is she manages to pull off a performance that makes me say, “oh that woman is crazy and I would never want to be left alone with her,” while at the same time thinking, “oh that woman is crazy and I wouldn’t mind being left alone in a room with her.” Ultimately Diaz’s is given one job and it’s to make us believe that Cruise’s character would make the one big mistake that he makes and she delivers.


Penelope Cruz is essentially being the Spanish version of Natalie Portman from Garden State. In other words, the perfect woman that any man would be happy to fall in love with. In a way, she has one of the toughest roles in the film because she needs to be perfect enough for us to understand everything that Cruise has decided to do to keep her in his life. She also needs to be great enough to make us hate the one big mistake that’s made by our main character and much like Diaz she is perfect in this role.

I already mentioned Kurt Russell and obviously, this man could read a phone book and he’d still come off as one of the most charismatic men ever. He does do a great job playing the father figure character for Cruise. In a way, Cruise’s character isn’t very relatable and it’s Russell’s job to convince the audience that, at the very least, you want to like Cruise’s character.

And lastly, we have Jason Lee who, while essentially playing Jason Lee, is given a daunting task of having almost all of his scenes be with Tom Cruise. In 2001, Jason Lee was mostly known for being one of Kevin Smith’s actors and while he did a great job in Chasing Amy, it wasn’t a guarantee that he would be able to share the screen with Cruise. It’s obvious that Lee understood the task and that he would have to bring his A-game because that’s what he did. Going back and watching this movie, I’m left thinking, why didn’t Jason Lee go on to be a bigger star? I’m sure he’s loving that “My Name is Earl,” and “Alvin and The Chipmunk” money, but damn it, he deserved better.

I said I wouldn’t break this film down scene by scene and I won’t because this is a movie that everyone needs to see and I don’t want to give away too much. Even as I discuss the ending of the film, I promise, I’m not going to spoil what happens.

So, as audiences come to the end of the film and finally learn what the entire story is about, they are met by the movie’s big questions. What if you could go back and fix your mistakes? What if you could go back and make everything perfect? What if you could go back and fix that one mistake that changed everything? And what would happen if after you’ve lived that perfect life, you had a chance to do it all over again? If you knew that could make it so that every day would go exactly how you wanted it, would you truly be happy? Is that what life is all about, or is it about waking up every day and dealing with the decisions that you’ve made in the past? See, Vanilla Sky doesn’t have aliens or memorable catchphrases but what it does have is moments and questions that will leave you with thoughts that aren’t only about the movie but about yourself. Maybe a movie like that isn’t for everyone, but for me, it’s the reason why Vanilla Sky is Tom Cruise’s best movie.


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