Things are not always what they seem

I'm making Vanilla Sky my entire personality

I love a cast photo that doesn’t relate to the movie at all.

As soon as the Oscars ended, my desire to watch something old and non-trending came roaring back. I chose to watch Vanilla Sky, for reasons that are unclear even to me. Was Tom Cruise on my mind after seeing Jimmy Kimmel make fun of him during the ceremony? Was I trying to finally make my way through all of Cameron Crowe’s films after my Say Anything rewatch? Or was it…fate?

Because the second this movie ended, I wanted to hit the streets and start asking my neighbors, “Have you heard about Vanilla Sky?” I wanted to make a flag for my home out of the movie’s poster. I wanted a bumper sticker that says “Pardon My Driving, I’m Thinking about the 2001 Cameron Crowe Film Vanilla Sky.”

Saying I enjoyed this movie seems almost too simple, because I’ve been wrestling with my feelings for it for the past week. I love it when I watch a movie and I’m initially confused, maybe even repelled, until my dislike turns into something akin to appreciation and then transforms again into something that might be love (which was my journey with Take This Waltz).

Vanilla Sky is a movie that I should’ve watched when it came out in 2001. There were a lot of confusing, memory-related movies coming out at the time (like Memento) and I loved them, because I was in high school. A movie with any sort of twist is naturally going to hit different when you’re a literal child who just hasn’t seen that many movies yet—your expectations haven’t been set or spoiled by a million other twist movies. I would’ve, in short, made Vanilla Sky my entire personality, because it’s a complex movie that rewards multiple viewings, and I had nothing but time to rewatch all my favorite movies in my parents’ basement. Also it was Cameron Crowe, who I already loved for his soundtracks that were cooler than any mix CD I could ever make.

But I’m glad I didn’t watch it back then, because it meant I got to have a delightful, exhilarating, all-around confounding experience watching it last week as a 36 year old. Imagine me watching it as that Liz Lemon gif. Yes to streaming movies!

Anyway. Do you want to know what happens in this film? Do you dare? Chances are good that you already know, give that it’s over twenty years old, but be warned: spoilers abound. I am going to describe this entire movie, and it’s a movie that will be much more enjoyable if you don’t know what’s going to happen on your first viewing (I mean, probably…maybe you do want to know, I don’t know your life). Okay. Ready? Let’s go.

So Tom Cruise is Tom Cruise: floppy hair, distractingly fit, face chiseled out of marble. His friend with benefits is Cameron Diaz, who you suspect might actually want a little more out of their relationship. Tom Cruise doesn’t care. He seems to think that if he repeatedly says they’re just friends, the mere uttering of the words will make it true. You get the idea that this is how he gets through life. His name is David Aames, but I will call him Tom Cruise.

His best friend is Jason Lee, playing a Jason Lee type (novelty t-shirt, slightly put-upon, self-deprecating). He shows up at Tom Cruise’s party with a date he just met: Penelope Cruz. A fun fact is that Penelope Cruz played the same role in the Spanish movie Vanilla Sky was based on, Abre los Ojos. Keeping the same cast in remakes is something I find fascinating. Like when David Tennant played the same role in the American version of Broadchurch, and he had an American accent?? David Tennant with an American accent should be punishable by law.

Back to Vanilla Sky. Tom Cruise and Penelope Cruz hit it off immediately, probably because they have similar last names. They have such a great time together that he ends up going back to her place. She’s a dancer and has an exciting life that’s expressed through artistic photographs strewn about her apartment, because she’s a Cameron Crowe Woman. Tom Cruise stays over and when he leaves in the morning, who shows up but our girl Cameron Diaz. She’s rolling down the street in a very cool blue car, leaning out the window and attempting to be laissez-faire, despite the fact that she’s clearly stalking Tom Cruise. If Tom Cruise were a smarter man, he’d realize that Cameron Diaz has non-friend Feelings for him, but instead he just says “we’re friends!” again like that fixes the problem. Because none of his actions have ever had consequences, he gets in the car with Cameron Diaz, a woman he knows loves him, despite just having spent the night with Penelope Cruz.

This is where the movie switches from your typical Cameron Crowe joint to…something else entirely. Because what do you think Cameron Diaz does on their drive around town? Does she have a heart-to-heart with Tom to a nostalgic soundtrack? No. Instead, she tells him she loves him and says something so hilarious, so evocative, so specific that it will live forever in my head. I’m afraid to type it out so here’s an image:

And then…SHE DRIVES THE CAR OFF A BRIDGE. We’ve taken such a turn away from Cameron Crowe land! She dies and Tom Cruise is horribly injured, specifically on his face. You know, his beautiful Tom Cruise face? The one he’s so proud of?

I know I said I was going to spoil this whole movie, but the truth is—I could type out literally every plot point and it wouldn’t make any sense. I have no idea how I could tell you whether this movie is good or bad. It exists in some entirely unnameable third category. It was famously divisive upon its release, in a way that I don’t think it would have been if not for the director or the sheer star power. This was Tom Cruise starring in something weird and confusing, from a director who just made Almost Famous, a universally beloved movie. Up until this point, pretty much all of Cameron Crowe’s films were universally beloved. This one, though, was baffling because while it has all the Crowe trademarks—the soundtrack featuring Peter Gabriel, the dad issues, the quippy little one-liners meant to be repeated and/or featured on a t-shirt—it also has many things heretofore unseen in Crowe films (a car crash that kills Cameron Diaz, for starters). And many people simply did not want these things; the movie’s Rotten Tomatoes score is a measly 43%.

And at first, I have to say that I agreed with the consensus. There are a lot of things about it that feel contrived and absurd and frustrating. Like, Tom Cruise wears this mask for a lot of it.

Also the plot doesn’t make sense for about ¾ of the movie. Things are happening in ways that make sense after you see the entire film, but as they’re happening, it’s unclear if they are harbingers of something sinister or simply bad storytelling.

And yet. And yet! I desperately wanted to know what was going to happen in this film, and the second I finished it I was googling Cameron Crowe interviews and theories. It was all I could think about for the next week. I listened to the soundtrack so much that when we got in the car this weekend, my six year old asked if we could listen to Can We Still Be Friends (the answer is yes, always).

So what is it about this movie that bewitched me, body and soul? I need to tell you in list form.

The music is, no surprise, quite good.

Cameron Crowe knows his way around a soundtrack. The Elizabethtown soundtrack is one of my all-time favorites (this is an Elizabethtown-hate free zone! Leave your smack talk at the door! Let none of us criticize a film where Susan Sarandon shouts “BONER!” at a banquet room full of people). Vanilla Sky feels very early-2000s (Radiohead, The Chemical Brothers) but still features the timeless jams we’ve come to expect.

One of my favorite scenes is when Tom Cruise and Penelope Cruz draw portraits of each other as Solsbury Hill plays.

This scene is hilarious because Penelope Cruz is apparently moonlighting as a boardwalk caricature artist. But that’s not the point here. The point is…this song is one of my favorites, and it fits in perfectly with this scene and with this film. The guitar is deceptively light, making the song at first feel almost romantic. But there’s something about the music that has always felt sadly nostalgic to me, as if Peter Gabriel is recalling a wonderful moment that will never come back again (the lyrics themselves are apparently about deciding to leave Genesis and go solo, but given that I can’t relate to that I’ve come up with my own meaning). Cameron Crowe has said that he chose songs with lyrics that correspond to the plot, and boy, do they ever. “I did not believe the information/Just had to trust imagination.” “To keep in silence I resigned/my friends would think I was a nut.” Tom Cruise’s friend Jason Lee does think he’s a nut! Picture my heart going boom-boom-boom whenever I hear this song.

I’m a sucker for a Todd Rundgren song in a film (see: The Worst Person in the World). But he’s never been used to such incongruent, horrifying effect as he has in Vanilla Sky. Tom Cruise is at the height of his confusion/breakdown, unable to keep a grip on reality, convinced that Cameron Diaz has come back from the dead to torment him. This scene would be impossible to describe, but just know that the climax of the song (when Todd Rundgren starts singing “La la lala, la la LA LA,”) is perfectly timed with Tom Cruise discovering…Penelope Cruz’s mole! This movie hinges on A MOLE. I’ll never hear this song the same way again. The scene itself isn’t on YouTube so enjoy some pictures of Tom Cruise and Penelope Cruz!

Cameron Diaz is so good.

Whatever you do, don’t get in a car with this woman!

Her role is one that could be pretty one note. Basically, she’s the Glenn Close in Fatal Attraction of this film. But where Glenn Close added depth to that character by being sort of soft and sad, Cameron Diaz starts out as the cool girl we all know her as and then surprised me by really going off the rails. I never really thought about whether she was a good actress or not, and I’ve primarily watched her in rom-coms, but she has some range. I wish she hadn’t retired from acting, but also I respect and understand that.

Cameron Crowe left it all on the court.

Does that metaphor work? My husband has basketball on at all times right now. Well, what I’m trying to say is that Cameron Crowe filled every single frame of this movie with details that reward you if you think back on them. Every piece of décor, every song, every sound, every character. They all mean something.

And that really hits on what I appreciate so much about this movie: everyone involved was really trying to make something singular. It made me think of a recent movie with a (honestly, pretty similar) twist: Don’t Worry, Darling. I had a good time watching it, but when it ended I wasn’t satisfied at all. That’s because there were a lot of things that simply didn’t make sense. It didn’t feel like anyone was making sure that every detail of the movie pointed to the ultimate conclusion.

In Vanilla Sky, there’s never the feeling that Cameron Crowe has abandoned you. Whether you like it or not, he created the exact thing he set out to make. The movie is complex, to put it lightly, and there isn’t an easy explanation for what happens. But! Cameron Crowe actually lists six popular theories on his website, along with many of the little easter eggs that might go unnoticed. Talk about attention to detail.

This all makes me a little sad, because I think it’s harder to make movies like that these days. Of course there’s Everything Everywhere All At Once, a movie that was both a critical and commercial success while clearly being a product of its directors’ visions and being filled with tons of tiny details. But how many other movies are like that? Netflix recently pulled the plug on Nancy Meyers film because the budget was too big. And that’s Nancy Meyers! It’s increasingly rare that anyone will invest serious money (or time, or confidence) in a director’s unique vision.

So what happens to Cameron Crowe in a film climate like this? I’ve spent all week thinking about the strange trajectory of his career. Vanilla Sky was the sudden point where many people got off the train. This wasn’t Say Anything or Almost Famous, and even though he did return to form with Elizabethtown, it was almost like Vanilla Sky broke the spell. I still haven’t seen Aloha, but all I know about it is a) Emma Stone’s character and b) the Sony hack.

If you’re lucky enough to have a long career, you’ll have ups and downs. Every movie, or book, can’t possibly be better reviewed and a bigger moneymaker than the one before it. I have my seventh book coming out this year, and this is something I think about a lot (not comparing myself to Cameron Crowe, lol). When you have a body of work, people are naturally going to have favorites and least favorites. But what do you do when something receives an outsized amount of negative attention? Does that affect your ability to keep creating meaningful work?

Luckily for me/us, Rachel Handler did a truly fascinating interview with him and straight up asked him if Vanilla Sky gave him the yips and then asked how he’s been affected by his most recent films not doing well critically or commercially. His answer:

“I always equate it to artists that I love. If Joni Mitchell puts out a challenging album, for example, I’m down for it. My fandom says, “I’m with you. I wanna go where you’re going. I like the early stuff, I like the later stuff, I just like your stuff.” I just like putting a voice out there — for better or for worse, how I look at the world.”

That’s the answer of someone who’s at peace with his creative output. Throughout the interview, he sounds happy and grateful to talk about this film that clearly meant a lot to him. He never sounds defensive or angry. The whole interview is absolutely worth reading if you’ve seen the film and you want to hear some fun, behind-the-scenes secrets. It sounds like everyone involved was having a great time (which certainly doesn’t sound like the case on Aloha).

Maybe we’ll get another heartfelt movie out of Cameron Crowe yet. Or maybe we’ll get another big, weird, messy, confusing movie. Either way, it sounds like he’s doing all right.

Vanilla Sky is currently streaming on Kanopy, Amazon Prime, Fubo, and Paramount+ (according to JustWatch, perhaps my most-visited website).

Next week is my first monthly round-up for paid subscribers. If you subscribe, you can hear all about what I’ve been reading (my first Colleen Hoover??), watching, and thinking about. See you next week.