Tom Cruise’s career had now entered its fourth decade, and in all that time there is one stretch that stands out as the most interesting. It begins in 1996, which brought us two of the most important films of his career: the original Mission: Impossible (covered previously) and Cameron Crowe’s Jerry Maguire. The former is notable for sending Cruise down the action hero path that would eventually lead him to his current state, and the latter is a memorable quote factory that was able to get not one, but two lines onto AFI’s 100 Years… 100 Movie Quotes list, with a third just missing the cut. It’s the film that got Cruise his second Oscar nomination, and for the next few years he continued to chase that dragon, resulting in perhaps the three weirdest movies Cruise has ever starred in: Eyes Wide Shut, Magnolia and Vanilla Sky.

However, let’s stay in Jerry Maguire land for the time being. Like many other Cameron Crowe protagonists, Cruise’s Jerry Maguire is a relentless optimist who spends most of the film trying to figure out just what his purpose is. Right from the start, he is a fundamentally good person who just hasn’t quite realized his full “goodness” potential. It’s an incredibly cheesy movie, but Crowe does cheesy better than just about anyone, and when Jerry and Renée Zellweger’s Dorothy meet at the end for their climactic declarations of love, it feels absolutely genuine. Crowe doesn’t make a movie unless he buys into the things he is writing, and that clearly trickles down to his actors. Cruise portrays the typical Crowe protagonist incredibly well, and it’s one of those performances that is so natural I’m surprised the Academy even noticed his work. It’s certainly one of his best performances, but it isn’t anywhere near as showy as what he did in Born on the Fourth of July, and what we would later see in Magnolia.

But as I am a slave to chronology, we must first stop at Eyes Wide Shut, the final film by Stanley Kubrick, and even by his standards it is a weird one. This was a filmmaker who spent most of his career looking outward, making films that had very little to do with issues that were close to him. His approach was cold, calculated and exacting; pretty much the opposite of Crowe. However, Eyes Wide Shut sees Kubrick perhaps getting a little more personal than normal, even though the subject matter had very little to do with his own life. This is, quite explicitly, a film about marriage, but it explores this subject in a profoundly unusual way. On top of that, it’s done with all the emotional warmth you’d expect from the man who brought you A Clockwork Orange and The Shining.

As for Cruise’s work in the film, he is asked to be something of a blank slate and/or audience surrogate. He observes and reacts far more often than he projects. The more attention-grabbing performance undoubtedly belongs to Nicole Kidman, who gets the film’s best dialogue, and her marijuana-fueled monologue early in the film essentially sets the rest of the “plot” into motion. (And then there’s Kidman’s final line, which is perfection.) It’s a very good performance from Cruise, but like many an actor before him he amounts to little more than Kubrick’s plaything. The vast majority of the film sees him walking around various locations looking confused, but he sure does sell it.

One of my favorite things about Eyes Wide Shut is how it initially doesn’t feel much like a Kubrick film at all. Early scenes are driven almost entirely by dialogue, as Cruise and Kidman are separated during a get-together at the house of Victor Ziegler (Sydney Pollack). They both face brief temptations, but nothing comes of them, and then they return home for a chat that eventually leads to the aforementioned Kidman monologue. That sends the film into Kubrick hyperdrive. As Cruise’s character walks through a fake, manmade New York City, the streets feel as though they are closing in, not unlike the hallways seen in The Shining. And then there is the famous orgy scene, which Kubrick films with his typical emotional distance. Like most of the nudity in his films, it doesn’t feel the least bit erotic. It might achieve that effect if our hero was supposed to be there. As it is, the whole ordeal just feels downright creepy.

Speaking of creepy: Tom Cruise’s character in Magnolia. Toward the end of my high school days and into my first couple years of college, I would name this as one of my favorite movies ever. In the couple years since then it has fallen a bit by the wayside, and with this viewing all of its flaws started to bubble up to the surface. I still love it, but as more of an ambitious mess than an ambitious masterpiece. However, when you’re first getting into “serious” movies in your late teens, Anderson’s style in Magnolia is quite the drug. The camera is moving all over the place, there are long takes galore, and the whole thing just feels like it means something, dammit. However, the more movies you watch, it doesn’t quite amount to what Anderson thinks it does. This is a case of an impossibly talented young filmmaker still trying to figure it all out while also trying to make Something Important. These 15 years later, with There Will Be Blood and The Master under his belt, I think it’s safe to say Anderson now has it figured out. And how.

While Magnolia is no longer one of my favorite movies, it still might have my favorite Cruise performance, which is odd considering he’s not actually in it all that much. Even so, he makes every second count, and he announces his presence with an incredible introduction set to “Thus Spoke Zarathustra.” The applause is rapturous as he takes the stage, and then dives headfirst into his filthy, misogynist monologue. Like many of Cruise’s best performances, it starts by presenting a hyper-masculine image—in this case taken to its comic extreme—and then slowly undercutting it until all the confidence and false bravado is gone, and he is left a sobbing mess next to his estranged father’s deathbed. He is introduced at the height of his powers, and then discarded at his lowest point. Magnolia is a three-hour parade of misery, but Cruise is able to turn his arc into one of the most memorable.

One big reason for this is that Anderson chooses to give Cruise some of the film’s quietest moments, and there aren’t many of those to be found in Magnolia. Watching it now, the most frustrating thing about it is the way Anderson is far too eager to cut away from key scenes right when they’re starting to get interesting. He almost seems afraid to stay with one character too long, but when he chooses to leave people in the middle of an emotional, important conversation, it feels like he’s letting them off the hook. It’s no coincidence that the best scene in the film comes when all the major characters stop for an impromptu sing-along to Aimee Mann’s “Wise Up.” It’s certainly a weird scene, but it’s also the most emotionally effective. Not unlike Cruise’s character, the real emotions in Magnolia don’t come out until the fireworks are put away.

After 1999’s one-two punch of weird with Eyes Wide Shut and Magnolia, Cruise returned to filmmaking of a more mainstream sort with Mission: Impossible II. However, he wouldn’t stay away for long, and in 2001 he returned to the loving embrace of Cameron Crowe for the ambitious Vanilla Sky. Those expecting another Jerry Maguire were in for a big surprise, since this was to be an English-language remake of the Spanish thriller Open Your Eyes, and Cruise winds up spending most of the film either sporting a disfigured face or a horrifying nightmare mask (see above). While Crowe’s film is often creepy, he avoids turning it into a straight Twilight Zone-esque thriller and instead engages with the emotions behind the premise. The plot is the last thing on Vanilla Sky’s mind, and that is why I wound up liking it far more than I anticipated.

It’s still a mess, since making a film this weird and ambitious is uncharted territory for Crowe. Right from the beginning you know Vanilla Sky is playing a different game, and the wonderful opening scene—set to Radiohead’s “Everything in its Right Place”—sets the audience up for something that is going to be very much out of the ordinary. Crowe eventually delivers on that promise, and he clearly connects with the material, but ultimately mind-bending “idea movies” are a bit of an odd fit for his sensibilities. This is a film about dreams and memories, but Crowe’s style could have found a way to embrace those sensibilities more completely. Also, the performances from his actors never quite find a way to mesh. Cruise is quite good in the lead, but most of the supporting players fail to leave an impression. In particular, casting Penelope Cruz to reprise her role from Open Your Eyes was a mistake. That role needed someone who could have impeccable chemistry with Cruise, and that never comes to fruition here.

But forget all that, because Vanilla Sky is one of those movies that I appreciate just because I admire that it even got made by a major Hollywood studio. It turned out to be a sizable hit too, showing just how willing audiences were to follow Cruise wherever he went. That’s what I love so much about this tiny era of Tom Cruise movies: he was able to make things like Eyes Wide Shut and Vanilla Sky and still get butts in the seats. His experimentation continued on into the next decade, but there came a point where Cruise decided to start exploring far safer options. In fact, the closest he’s ever come to creating another Frank T.J. Mackey is Tropic Thunder, where he portrayed Hollywood producer Les Grossman. They are obviously not the same man, but it’s still a welcome change from the norm that allows Cruise to show just how strange he can be when given the chance. Perhaps the day will come where Cruise gets weird once more. We can only hope.

Next time: In the early 2000s, Cruise went dark for two Steven Spielberg sci-fi joints, and went bad for Michael Mann’s Collateral.