Jane Fonda hands me the Palme d’Or and I stand there for a moment, waiting for the applause to stop and trying to figure out what to say and trying not to fall apart. I looked out and said “Well, I guess it’s all downhill from here.” —Steven Soderbergh’s journal, 5/23/89

Over the near-decade that followed that night in Cannes, Soderbergh’s quip came to sound more like than self-fulfilling prophecy than facetious modesty. The 26-year-old wunderkind’s debut feature, Sex, Lies, And Videotape, won Cannes, was nominated for an Oscar, grossed more than 20 times its modest budget at the box office, and made Soderbergh the toast of Hollywood. But he harbored no illusions of infallibility. Even while basking in Sex, Lies’ heat, he knew the score; a profile in Rolling Stone’s 1989 “Hot” issue notes, “Soderbergh can name half a dozen [directors] who have been the flavor of the month, and these days you practically have to put out an all-points bulletin to find out what they’re up to.”

Cut to March 1997, when Soderbergh attended a post-Oscar party thrown by Miramax, which had released Sex, Lies eight years earlier. “At one point,” he writes in his journal, “I was told I could not enter a certain elite section of the party while behind the guard/doorman’s head a trailer for Sex, Lies played on an enormous video screen. I figured that was enough irony for one evening.”

The next year, all that changed. His sharp, confident, frisky take on Out Of Sight put him back on Hollywood’s radar for good. After that “comeback” picture, his admirers came to regard the post-Sex, Lies, pre-Out Of Sight wilderness period as some kind of bad dream, a wandering walkabout by a talented filmmaker who’d lost his way. But that nine-year, five-film stretch is far too interesting—and too formative—for such tidy dismissals.

“I was realizing how many mistakes the success of a movie like [Sex, Lies] would buy me,” he later admitted. “I was very anxious to take advantage of that and try some stuff.” And try he did: Over that period, working both for studios and outside the system, he directed an original absurdist comedy, a thriller by another writer, a book adaptation, a stage adaptation, and a remake (as well as two episodes of a television anthology series). There were fleetingly recurring themes—primarily in the form of stubbornly isolated protagonists—but few stylistic links between them. “I’m a chameleon,” he announced in 1993. “Style is secondary to me.” But five years later, he admitted, “I didn’t feel formed yet. I still felt like I was very early on in my development.”

Sex, Lies, And Videotape gave Soderbergh the cinematic currency to make whatever he wanted. He decided to spend it on Kafka. He’d first read Lem Dobbs’ screenplay in 1985; it was one of those legendary unmade scripts that knocked around Hollywood for years, one everybody loved but no one dared to make. “I was going to get my head handed to me on my second film, pretty much no matter what I did,” he recalled. “In a way, I decided I would go out in flames by making a film that really had a big red bull’s-eye on its chest.”

From Kafka’s opening sequence, a very different Soderbergh is at work. Sex, Lies is noteworthy (particularly compared to the debut films of earlier 1980s sensations like Spike Lee and the Coen brothers) for its almost invisible style—Laura San Giancomo’s Jaws-inspired reverse zoom aside, the film is refreshingly free of whiz-bang camerawork and overcooked effects. Kafka, however, is filled with Dutch angles, roving dollies, and German Expressionist lighting; it feels at times like the filmmaker showing off in a way he hadn’t before. The picture seems self-conscious of its flourishes and influences (The Third Man, Welles’ The Trial, M, early Lynch, Brazil), and while the form is impressive, the content is constantly playing catch-up. It’s wildly ambitious and exquisitely rendered, but emotionally hollow.

Kafka uneasily mixes mystery, noir, comedy, horror, mad-scientist tropes, and movie/book nerd in-jokes. It’s clear why Soderbergh was drawn to the challenge of Dobbs’ script; to have pulled those disparate forces together into a cohesive whole would’ve been a real accomplishment. And there are moments, and even full scenes, where he does just that. But ultimately, it was out of his grasp. “The mistakes in Kafka are the classic mistakes of a young filmmaker, which is inconsistency of tone,” he admitted recently. “It was physically a larger movie, obviously, than my first film and I was very conscious of the craft of it all. And I think that was at the expense of really analyzing the screenplay and figuring out what the tone of it was.”

No such difficulties plagued his adaptation of A.E. Hotchner’s memoir King Of The Hill. Soderbergh’s second straight period piece—this one set in St. Louis, circa 1933—has a sleek, professional sheen befitting its studio pedigree. (It was an early production for Gramercy Pictures, Universal’s short-lived, indie-flavored boutique shingle.) Elliot Davis’ amber-hued photography gives the picture a warm, nostalgic radiance, which Soderbergh later pinpointed as its biggest flaw. “It’s a beautiful film to look at—I just think, in retrospect, that was kind of the wrong approach,” he says on the film’s recent Criterion disc, wishing instead that he’d gone with a “rougher, grittier feel” to compliment his young protagonist’s struggle through Depression-era poverty.

Perhaps. But the incongruity of the imagery to the narrative delivers a more powerful visual message; by dressing up the picture in the golden glow that envelops so much of how we feel about the past, the unpeeling of genuine misery, fear, and unhappiness underneath makes a greater impact, particularly in the visceral climactic scenes that find young Aaron (Jesse Bradford) nearly starving to death.

Whatever the case, there’s no denying King Of The Hill’s primary value in the Soderbergh oeuvre: After a debut film that alienated some viewers with its deliberate coldness and a follow-up that was, in the filmmaker’s own view, “hermetically sealed,” King Of The Hill was his most nakedly emotional effort to date. (Or perhaps ever.) Aaron’s bittersweet first kiss, his public humiliation in front of his classmates, his separation and reunion with his younger brother, the joy of exploring their new home—this is real wet-hanky stuff, and Soderbergh’s confident writing and directing prompts those emotions without clumsily reaching for them with maudlin effects.

Soderbergh returned to Gramercy for his next picture—the most disparaged, yet in many ways most important, of the period. The Underneath is a loose remake of the noir classic Criss Cross, a screenwriting paycheck from Universal that he’d originally intended only to write and executive-produce. But when he was pulled from Quiz Show at the 11th hour for Robert Redford (the conclusion of a strained relationship between the two filmmakers, dating back to King Of The Hill, which Redford was to produce), he decided to direct as well, to his almost immediate regret.

“It’s a very unpleasant feeling,” he explained recently, to “see everybody working so hard, the cast and the crew, to give you what you want every day. And you know that this thing’s just dead on arrival.” The issue was not problematic collaborators, or studio interference, or lack of funds. “I had everything I needed,” he said. “I’m the one that didn’t show up.” In a characteristically candid interview on the Criterion King Of The Hill (his regard for The Underneath is so low, it’s relegated to the status of humble special feature on another movie’s DVD/Blu-ray), he admits that the production occurred in the midst of both personal and professional turmoil, and viewing the film now, it feels like such exterior elements have colored his view of the work. There is an occasional airlessness to The Underneath, a sense that the film is, as he puts it, “just totally sleepy.” And for the first time, it seems that he’s aping a contemporary; the non-linear heist movie plays, in spots, like Soderbergh knocking off Reservoir Dogs. But it also boasts some daringly peculiar filmmaking; its best sequence, for example, is a seven-minute-plus scene shot entirely from the perspective of the protagonist, feverishly fading in and out of consciousness in his hospital bed. (“If the whole film had felt like that,” Soderbergh says, “then we might have had something.”)

“I can’t say that I would recommend it to anyone,” he adds, “other than to look at it in the context of a career.” But it is within that context that The Underneath is most enlightening. It features three of Out Of Sight’s key elements: a crime story, a fractured timeline organized with a hyper-saturated color scheme (see also: Traffic), and jazzily intercut pre- and post-sex scenes. The tense reunion between Peter Gallagher’s Michael and Alison Elliott’s Rachel plays like a dry run of Tess and Danny’s first scene together in Ocean’s 11; Rachel, a slippery fatale who unapologetically shrugs, “You know me, I like money,” is another of Soderbergh’s hard-edged, icy brunettes. (Other examples of note: Teresa Russell in Kafka, Sasha Grey in The Girlfriend Experience, and Rooney Mara in Side Effects.) And it was his first film shot in anamorphic widescreen, resulting in some interesting experiments and focus play—“things that I’ve done since, hopefully in a more successful way.”

By 1996, barely a year after its release, he’d already dismissed the film, with a caveat: “Even though The Underneath is my least favorite, in retrospect it may have been my most important film, because the dissatisfaction drove me into a new area.” In the Criterion interview, he recalls “a very specific memory of being under that underpass, shooting a scene with Peter and Alison, and thinking, ‘Okay, six months from now, nine months from now, I wanna be in Baton Rouge with a crew of five people, using the same methodology I used when I started making films.’”

The result was Schizopolis, shot in bits and pieces over nearly two years, with a five-person crew, for $250,000. Alternately described by its creator as “my take on the five years that I was married,” “my take on the creative act,” “a provocation of sorts and piece of agit-prop,” or an homage to “lowbrow variety-sketch movies like The Groove Tube and Kentucky Fried Movie,” its title card is a T-shirt worn by a pantsless mental patient, which is as appropriate a metaphor for the movie as any.

A series of loosely connected, often funny, often puzzling blackout sketches inspired by his love for Richard Lester, Schizopolis sends up Scientology, office drones, marriage, language, corporate intrigue, and dentistry. Soderbergh cast himself in the film’s two leading roles, and to his credit, most directors wouldn’t hand critics the ammunition of a scene of themselves literally jerking off. (Schizopolis has two.) He also cast his daughter and wife, from whom he’d recently divorced. Such familial casting touches—coupled with the low budget, found locations, and flat lighting—make Schizopolis feel much more like a first film than Sex, Lies, And Videotape. Which, from a creative standpoint, is exactly what it was.

Shortly after wrapping that film, still in Baton Rouge, Soderbergh segued into a quickie film adaptation of Gray’s Anatomy, Spalding Gray’s monologue about his desperate attempts to avoid eye surgery. They’d worked together previously on King Of The Hill; Gray’s monologues had been filmed twice before (Jonathan Demme’s Swimming To Cambodia and Nick Broomfield’s Monster In A Box), so Soderbergh decided early on to eschew the live-audience element, though he retains the monologist’s signature setup of a table, a microphone, a notebook, and a glass of water.

He then uses camera and lighting tricks to not only complement, but illustrate the story, replicating the narrator’s visual experience. It maintains its theatricality: sets, backdrops, cycloramas, lighting effects. But Gray’s Anatomy has a furious energy and improvisational inventiveness, neither of which are all that common in filmed theater pieces. “So many of the ideas that are in Gray’s Anatomy I would never have thought of or considered seriously had I not made Schizopolis,” he explained. “It is a willingness to drop everything and go after the better idea when it presents itself. That comes from security.”

“The Schizopolis/Gray’s period was really important for me because it was kind of a rebirth,” Soderbergh said in 2012. “I felt like I was starting over. It was a very conscious effort to rebuild myself as a filmmaker—to kind of tear down what I’d built in the first four films and start over… Part of what I was trying to bust out of was just this feeling of becoming a formalist, and having everything predetermined. So I was trying to find a way to work where there was a structured, improvisational feel to it, visually. Where you’re kind of planning it, and kind of making it up also. And I’ve continued to work that way.”

Both films, in other words, were part of an awakening as a filmmaker, a realization that he had no obligation whatsoever to follow any rules. And that spirit is what makes Out Of Sight so special. He was schlepping the films around the festival circuit and looking for distributors, with little luck (Schizopolis couldn’t even get into Sundance, where he was one of the most famous alums; it had to play across town, at Slamdance), when he got a call from Casey Silver at Universal. According to his journal, the studio head “asked if he could secretly slip me a copy of Out Of Sight… It’s a terrific script and all the people involved are good, so of course I called Casey the next day and turned it down.”

He changed his mind, of course, eventually realizing that the experiences he’d had in Baton Rouge didn’t have to exist separately from what he could do in Hollywood. He adopted a looser, less formal approach, even on bigger budgets; he kept his crews tight, eventually becoming his own cameraman, so he could be a more active participant. “For me, it was an explosion that continues to reverberate,” he said. “There’s no way I could have made Out Of Sight, the way I’d made it, if I hadn’t made Schizopolis or Gray’s Anatomy.” And he couldn’t have made those films, the way he made them, if he hadn’t gone out and—for lack of a better word—failed with those initial, ambitious Sex, Lies follow-ups.

And make no mistake: They were, from a commercial standpoint (and often from a critical one) failures. On the Sex, Lies, And Videotape DVD commentary, recorded shortly before Out Of Sight’s release, Soderbergh notes that his first film made more money “than anything else I’ve made, combined,” and he wasn’t even close to exaggerating; the most financially successful of the bunch was King Of The Hill, with a meager $1.2 million gross. (To put it into perspective, that figure was also Sex, Lies’ budget.) These were not films that were going to find a wide audience; some of them, particularly Kafka and Schizopolis, seemed to have been created expressly to alienate viewers. So what was Soderbergh up to? Challenging moviegoers? Seeing what he could get away with? Self-sabotage? All of the above?

“People kept thinking, He might do it again,” he told Peter Biskind in Down & Dirty Pictures. “And I’m very comfortable disappointing people. It’s like a real easy place for me to be. But I felt I was running out of time. What concerned me was, was I going to stay where I was and have the kind of career that is a footnote? I realized that I had a fear-of-success issue that I needed to confront.”

A fear of success would certainly go a long way toward explaining the choices of the post-Sex, Lies era; this is, after all, someone who fled Los Angeles for a farmhouse in Virginia after it hit. He didn’t want to be a part of the Hollywood scene—he didn’t want to make their movies. And, to his credit, he didn’t.

But was something else motivating him? If you know anything about independent-film production, his Sex, Lies companion timeline was shocking: He wrote the script in December 1987, rolled cameras on it the following August, and was the talk of Park City by January. Other filmmakers spent years scraping together the funds to make their first films, and even longer waiting for one to take off. Soderbergh hit a home run on his first at-bat. Did it all come too easily? Maybe he needed to fail, to take those risks, and run up against the boundaries of his talent and ambition, to puzzle out who he was as an artist, and what kind of filmmaker he was going to be.

Sometimes, when a director has a giant hit right out of the chute, they’re locked in, and end up making that same film over and over again. And that could have happened to Soderbergh; there was presumably some pressure (from financiers, and from himself) to keep delivering sophisticated, witty, adult relationship dramas, to become his generation’s Woody Allen. That would’ve been easy—but Soderbergh has never done the easy thing. He pushed back, and the work is richer for it—even the failures, which are still more stimulating than many of his contemporaries’ biggest hits. “Let’s put it this way,” he told Sight And Sound in 1999. “I don’t regret any of them. There have been good ones and bad ones, but I look back and think, ‘That’s an eclectic group of movies that, for better or worse, belong to me.’”

Our Movie Of The Week discussion of Out Of Sight concludes here. Don’t miss Tuesday’s Keynote on how the film cracked the Elmore Leonard code, and Wednesday’s staff forum on the film’s style, its use of its Florida and Detroit locations, and Leonard’s career. And join us next week as we don our feathered blonde wigs to talk about John Cameron Mitchell’s glam-rock musical Hedwig And The Angry Inch.