Tom Cruise has always been a risk-taker on the big screen, for good and ill. Lately, the risks he takes center around the physical — the ever-expanding Mission: Impossible franchise is now focused on the question of how far Cruise can push his body for the sake of entertaining the masses. Those risks feel all the more remarkable as Cruise approaches his 60th birthday. (He just turned 57 two weeks ago, a fact that seems…well, impossible.)

But the more Tom Cruise pushes his body, the further he moves away from the time when his risks were ballsier in spite of not being remotely physical. Just as it’s hard to imagine that Tom Cruise is pushing 60, it’s hard to believe that we’re now 20 years removed from a time when he worked on two massively risky projects that required his mental and emotional chops more than the physical: Stanley Kubrick’s Eyes Wide Shut and Paul Thomas Anderson’s Magnolia.

Fidelio

If Warner Bros. Pictures’ executives had their druthers, of course, Eyes Wide Shut might not be celebrating its 20th anniversary, because the film would have opened well before the summer of 1999. But Kubrick, the immensely brilliant perfectionist, was precise on every detail in what would be his final film, released posthumously. He died on March 7, 1999, just six days after showing a first full cut of the film to Cruise, his then-wife and co-star Nicole Kidman, and WB executive Terry Semel. The film would be released four months later.

Eyes Wide Shut was a multi-year production, and the impact was clear. If you look at Cruise’s body of work, you’ll notice a 3-year gap between his work as the title character in Cameron Crowe’s Jerry Maguire and playing the avatar in Kubrick’s exploration of sexual mores in New York City. It’s because Eyes Wide Shut started filming in November 1996 and didn’t end until June of 1998. During that time, Cruise was visited on the set by a young Turk who would direct the movie star’s next project.

Cruise didn’t need much convincing to work on Eyes Wide Shut, if only because Stanley Kubrick was Stanley Kubrick, and his space epic 2001: A Space Odyssey was the star’s favorite film. Cruise needed a bit more cajoling with Paul Thomas Anderson, even though the A-Lister had greatly enjoyed the writer/director’s previous effort. The sprawling 1997 film Boogie Nights had managed to both ring up a great debt to filmmakers like Martin Scorsese and Robert Altman while feeling distinctly fresh and original.

The Past Ain’t Through With Us

That paean to the world of pornography was a blast of fresh air to many cinephiles, and did well enough that New Line Cinema gave the director a blank check, the likes of which Anderson knew he wouldn’t get again. So he wrote an even longer film with even more characters, a three-hour-plus epic set in the San Fernando Valley, focusing on a group whose interconnections are revealed over time, before a literally biblical, inexplicable act unites them all on a dark night of the soul. One of the many characters, a misogynistic lothario who preached sexual self-help tips to faux-macho guys, was who Anderson wanted Cruise to play.

The timing wound up being serendipitous, as a representation of the polar opposite of what Cruise was doing with Kubrick. It’s not just that Eyes Wide Shut and Magnolia vastly different from each other — on the whole and within Cruise’s performances — but they’re radically different from the rest of Tom Cruise’s filmography of the last 20 years. For Eyes Wide Shut, Cruise allowed himself to be at the mercy of one of the most famous perfectionists in the business. And unlike many of the A-lister’s future roles, his lead character is the total inverse of the cocksure hero of films like Risky Business, Top Gun, and Jerry Maguire. Dr. Bill Harford looks as debonair as Cruise, but it’s all on the surface of an otherwise helplessly neutered individual.

He’s married to a gorgeous woman (Kidman, natch), but Harford drifts through his life in New York City with such naivete that his entire life feels upended when, early on in the story, his wife Alice reveals a sexual fantasy inspired by a passing encounter with a stranger, so intense that she imagined leaving her family behind. Harford’s response is that of flight: he comes close to sleeping with a number of other women over a long emotional journey, without ever actually consummating any of the trysts. The culmination of his exploration of the seedier side of his swanky life is a baroque orgy that he crashes, before being humiliated in front of the invitees for having essentially broken in.

Bill is a profoundly ineffectual character – he’s warned by various characters, from an old friend (Todd Field) to an overly obsequious desk clerk (Alan Cumming), about the underbelly he’s trying to investigate, but doesn’t actually change much in his life. Both in the opening and closing of the film, Alice is a much more impactful part of their marriage, with a killer last line that cements who holds the power in their relationship. It’s both ironic and weirdly appropriate that, for all the marketing about Eyes Wide Shut relating to its sexual content, its orgy sequence, and the Cruise/Kidman dynamic, that characters talk a lot about sex without ever having sex. It serves as a perfect way to neuter Cruise’s inherent charisma.

I Will Not Apologize For What I Want

Similarly, in Magnolia, we never see Cruise’s character, Frank T.J. Mackey, do the deed. With Frank, though, there’s a lot of talk about sex, about the female mind, and about how any man can get into a women’s undergarments simply by playing the right series of mind games. While Frank T.J. Mackey never is depicted having sex, there’s never really any doubt that he’s likely been with a few women in his time. (Or, if you like, he’s a lot better at acting like it than Harford ever could be.)

By the end of the film, it’s painfully clear that Mackey’s intensely misogynistic view of men and women is a darkly cynical mindset instilled in him by his gruffly absentee father. That would be the now-dying TV producer Earl Partridge (Jason Robards), who left Frank’s birth mother behind and is currently in the throes of incomprehensible regret at such actions. As gruff as Earl once was, his barely coherent wish to his nurse (a beatific Philip Seymour Hoffman) is to reconnect with his son, which leads to Frank, a motivational speaker of sorts.

At the start of a very eventful day documented in Anderson’s sprawling Southern California opus, Frank is introduced to a series of largely faceless, cheering dudes in a hotel conference room. (It’s all too fitting that Frank is brought on stage with the pomp and circumstance that could only be provided by the bombastic Richard Strauss piece of classical music “Thus Sprach Zarathustra”, famously associated with Stanley Kubrick’s 2001: A Space Odyssey.) His first words set the tone for Cruise’s blustering, swaggering performance: “Respect the cock…and tame the cunt!” It’s an almost jarringly profane version of Tom Cruise, the pure-id version of his prior heroes, the same ones being almost laughably shunned in Eyes Wide Shut.

But Frank is cut down to size over the course of the three-hour-plus running time – after we see his first presentation, a kind of version of the infamous The Game (not the David Fincher film), in which men act cruelly to women to get the fairer sex to give them their prurient desires, he’s interviewed by a female journalist (April Grace). All seems well at first, until Frank realizes (and tries to hide this awareness) that she’s uncovered his true history, the reality behind his bluster. Frank veers from his initial charm to grouchy pouting (as he icily states, “I’m quietly judging you” to one of her questions) to actively attempting to attack her. And then Frank learns that his father is on death’s door.

These Strange Things

Cruise’s performances in these films run the gamut, from the internal to the external. His work in Magnolia is more mature and adult than his action-movie fare, but more in line with starring roles in The Firm or A Few Good Men than his henpecked husband in Eyes Wide Shut. If you look at Cruise’s filmography in the subsequent 20 years, you’ll mostly just find a lot of genre fare. Notably, Cruise has doubled down on his action-hero status since these films opened – five of the six Mission: Impossible films have been released in that period, including the 2006 entry where Hoffman played a terrifying villain.

Cruise has also limited the directors with whom he works, relying on a few favorites such as Joseph Kosinski, Christopher McQuarrie, and Doug Liman. (Kosinski is behind the camera for Top Gun: Maverick, taking over for the late Tony Scott.) Though he’s worked with more iconic, auteurist directors too, it’s been in more straightforward, action-heavy titles like Minority Report and Collateral. It’s not that these films are bad – those two specifically are excellent. But the challenges of movies like these or the Mission: Impossible series or Edge of Tomorrow is that Tom Cruise puts his body through the ringer.

It’s exhilarating to watch Tom Cruise dangle off a building or a plane. But as he reaches his sixties, it’s just as exhilarating to imagine what it might be like when he eases into an era during which his body just won’t let him keep destroying itself. We’re a long way removed from films like Eyes Wide Shut and Magnolia, but they both prove that there was once a time when Cruise was willing to push himself, both with established and up-and-coming directors, and to do so mentally as opposed to physically. We can only hope he returns to this mindset soon.