In an interview with The Guardian earlier this month about the release of his new sci-fi thriller Gemini Man, in which Will Smith plays an elite assassin squaring off against a cloned version of his younger self (“played” by a de-aged CGI Smith), Ang Lee was asked about his earlier foray into the world of digitized character study. “The first Spider-Man came out when I was shooting Hulk, and here I was shooting psychodrama,” the director said. “I had absolute freedom, which may be good or bad. Whatever I wanted, at any expense, was mine, it was like I was on a shopping spree. I’m still proud of Hulk, but I underestimated the power of genre and how you have to wrestle with a general audience.”

Lee’s description of his first and only comic book movie as psychodrama is apt: dotted with surreal dream sequences and pivoting on the Oedipal conflict between Eric Bana’s Bruce Banner and his monstrous father, Hulk remains perhaps the most simultaneously cerebral and open-hearted film produced under the Marvel banner—a flawed but unmistakably personal piece of work that might even give Martin Scorsese pause about whether it qualifies as “cinema.” It was also, as Lee suggests, the turning point in a filmography which to that point had earned the Taiwanese-born filmmaker the artistic and financial equivalent of a blank check.

For the first two decades of his career, Lee had built a persona as a kind of transnational shape-shifter, moving seamlessly from culturally specific comedy-dramas like The Wedding Banquet and the Oscar-nominated Eat Drink Man Woman to the critically acclaimed English-language hits Sense and Sensibility and The Ice Storm. All of these films are, in some way or another, comedies of manners, featuring characters bumping up against social mores and restrictions; the suburban ‘70s critique of The Ice Storm, with its swinging couples swapping partners during a deep freeze, is particularly withering about the gap between what people say they believe and what they do behind closed doors. With Crouching Tiger, Hidden Dragon, Lee split the difference between his personal cinematic heritage and a post-Tarantino gentrification of genre cinema and wound up with a global phenomenon.

In Crouching Tiger, Lee wielded the “power of genre” like the Green Destiny sword itself—the film is a triumph of staging and showmanship. The same is true for Hulk, but as Lee implies, when it comes to their own pop-cultural reference points, American audiences aren’t as willing to meet ambitious artists halfway, much less fully on their own terms. The MCU’s tone of superpowered situation comedy (punctuated every so often by a portentous but ultimately reversible version of apocalypse) doesn’t risk alienation; by contrast, Lee’s “shopping spree” asked viewers to take the material’s themes of latent, suppressed rage and its potentially transformative effects seriously, with a bare minimum of banter. Fifteen years later, Hulk’s commercial failure has labeled the film as a false start in the 21st century narrative of superhero-movie box office dominance, or else as a cult item. Its true legacy, though, is how it propelled its director first into a creative depression during which he supposedly contemplated retirement, and then a “comeback” which has yielded an even more impressively varied slate of movies than his early period.

Lee earned his first Academy Award for Best Director for 2005’s Brokeback Mountain, a sensitive and spacious drama of two macho cowboys entwined in a clandestine love affair that was inevitably drafted into America’s culture war. The debate over whether or not Brokeback Mountain was either too explicit or not explicit enough in its style and imagery spoke to the challenge Lee, a straight filmmaker, had taken on by adapting Annie Proulx’s short story, as well as the ultimate complexity of his achievement. If Brokeback Mountain is a work defined by a sense of restraint, it draws that quality from the guilt and pathos of its protagonists. As the conflicted, uncommunicative Ennis, who refuses to sacrifice his family life on the altar of his attraction to his longtime lover, Heath Ledger served notice—probably for the first time—of being a major actor, and Lee’s measured, poetic image-making showcased the physical and emotional dynamism of his performance. When Ennis pummels an obnoxious redneck during a Fourth of July picnic, Lee shoots him from a heroic low angle that gives him the look of a vintage frontier hero, even as the fireworks suggest an incandescent inner frustration, a desire beyond the all-American archetype. It’s a sequence as expressionistically stylized as anything in Hulk—a mesmerizing tableau of mythic, simmering masculinity.

Where Brokeback Mountain was judicious with its eroticism, Lee’s follow-up plunged head-on into a different sort of controversy. Set in Japanese-occupied Shanghai and Hong-Long circa 1938 and 1942, Lust, Caution earned an NC-17 rating in the United States for its sexual content, with Lee refusing to re-cut the film for theatrical release. Freely adapted from a 1979 novella by Eileen Chang, Lust, Caution unfolds as a deluxe period espionage thriller, centering on a theater-student-turned-secret agent (Tang Wei) who is enlisted to seduce and assassinate a high-ranking member of China’s puppet government (Tony Leung) only to become ensnared in her own complicated and contradictory feelings. As a study of sex and power, the film has a conceptual elegance, deftly integrating serious ideas about resistance, occupation, and the moral ambivalence of love without sacrificing narrative momentum, and it’s beautifully made in an old-fashioned way: no less than Crouching Tiger, Hidden Dragon (or Hulk) it curates a serene gorgeousness in every frame. What really elevates Lust, Caution, though, is the directness of the sex scenes, which are desperate, brutal, and athletic in a way that seems to emanate from the characters themselves. The atmosphere is more melancholy than lurid; it’s like a hothouse that’s being warmed by dying embers.

Given the carefully crafted classicism and awards-season sophistication of Brokeback Mountain and Lust, Caution, it’s interesting how swiftly and significantly Lee’s position shifted in the ensuing years, away from an old-school storyteller into a Hollywood technocrat to rank with James Cameron or Robert Zemeckis. The latter actually makes for a pretty good point of comparison: in both cases, these are filmmakers whose mastery of their craft has inspired them to take on projects whose implicit logistical complexities constitute a genuine test of their abilities.

The pixilated specter of Hulk hovers over 2012’s Life of Pi, a project that attracted the attention of several visionary directors (including M. Night Shyamalan and Alfonso Cuarón) before Lee took it on and insisted on using 3D. Yann Martel’s novel about a boy adrift in the Pacific Ocean had been described as “unfilmable“ even as it presented spectacular possibilities for filmmakers willing to take on the challenge. “I thought of [it] half a year before Avatar was onscreen,” Lee told Roger Ebert. “I thought water, with its transparency and reflection, the way it comes out to you in 3D, would create a new theatrical experience and maybe the audience or the studio would open up their minds a little bit to accept something different.”

Even more than Avatar, Life of Pi obliges us to take a leap of faith across the uncanny valley. By pairing a human actor (Suraj Sharma) opposite a CGI tiger for most of its duration, the film went further than Hulk in integrating flesh-and-blood performance with animated “acting;” the connection deepens if you interpret the relationship between Pi and his carnivorous lifeboat companion as a metaphor for the former’s attempt to master his fears and develop a survival instinct. There is undeniably a self-allegorizing element to Life of Pi, which uses the framework of an adventure yarn to foreground themes of problem-solving (i.e., the details of living at sea in a small boat with a giant tiger) and technological innovation, as well as the act of storytelling itself. It’s a reading that turns the resourceful Pi into a surrogate for the director himself.

Life of Pi made $600 million worldwide and won four Oscars, essentially repeating the critical and commercial consensus of Crouching Tiger, Hidden Dragon. This time, instead of using his status to tackle a comic book property, Lee took a different sort of risk, adapting Ben Fountain’s 2012 novel Billy Lynn’s Long Halftime Walk, about an Iraq War hero invited to appear during a Dallas Cowboys game. Like Brokeback Mountain, the scenario lent itself to a thoughtful consideration of masculinity, with the added satirical potential of skewering the NFL’s culture of patriotic excess, and yet Lee opted to focus on a different section of his skill set. He announced that the film would be shot in 3D at an unprecedented frame rate of 120 fps, applying a costly, hyperreal digital aesthetic to a story that could easily have been told in a more conventional format. Billy Lynn’s Long Halftime Walk is a strange film, showing admirable fidelity to Fountain’s complex ensemble narrative amidst its director’s attempts at experimentation. In trying to cultivate a sense of realism, Lee ends up with something as stilted and artificial as a daytime soap opera: the clarity that comes with the high frame rate isn’t always kind to actors, whose tricks and mannerisms can seem exposed by the sheer clarity of the image. It’s a smart, humane movie filled with sharp ideas, and yet at all times, there’s the feeling of a filmmaker trying to negotiate the split between his dramatic instincts and his technological compulsions—an artist earnestly and interestingly at war with himself.

Gemini Man continues this trend on a bigger scale; this time, he’s using 3D (shot in 4k digital) and an accelerated frame rate in the service of a blockbuster-style narrative—one with its own built-in allegory in the form of Will Smith staring down his younger incarnation. Like Hulk or Life of Pi’s tiger, the character “Junior” is an entirely digital creation, and in a Q&A at the TIFF Bell Lightbox this week, Lee spoke thoughtfully about the process required to render his “performance.” “It’s about capturing a person,” Lee explained, comparing the process to a form of portraiture, as well as an extension of Smith as both an actor and a person. As cheesy as a lot of Gemini Man might be, the parallels between its clone-themed story line and its meticulous behind-the-scenes engineering make it into a proverbially rich text; it also features one of the most astonishingly conceived and executed chase scenes in recent memory (which culminates in what the director referred to during his onstage interview as “bike-fu”).

What came through most clearly during Lee’s remarks was his nervousness over Gemini Man’s massive budget. “I keep mentioning how expensive it is,” he joked after the third or fourth reference to making his financiers happy. “I hope I get to do this again,” he laughed, without giving the impression that he was kidding. Lee has good reason to be anxious, especially in light of his experience with Hulk. On one level, Gemini Man represents a similar sort of “absolute freedom;” on another, it’s constrained by its genre (which is most accurately described as “mid-’90s–Jerry Bruckheimer action movie”) and the necessity for a decent return on a reportedly gigantic investment. Once again, Lee finds himself wrestling with a mass audience, with the very real chance that he isn’t going to win.