‘Living In Oblivion’ at 25: Director Tom DiCillo On How He Turned The “Deepest, Darkest Period” Of His Life Into A Classic Of Independent Cinema

One of the most entertaining niche cinematic genres might just be the movie-within-a-movie. There’s something uniquely exciting about seeing a dramatization of what goes on behind the scenes of the filmmaking process, and contemplating the onscreen layers and how the director offers the audience a stylized look at something elusive to the average moviegoer while remaining fully in control of the entire aesthetic and narrative. Tom DiCillo’s 1995 film Living in Oblivion, which is celebrating its 25th anniversary today, is a low-budget indie that skewers low-budget indie clichés with droll humor and playful visuals and remains a model of the meta-movie at its creative peak. The film endures not just because of its stacked cast—featuring Steve Buscemi as the film-within-a-film’s director, Catherine Keener as its star, and Peter Dinklage making his debut as an actor who gives an unforgettable pissed-off monologue, to name just a few—but because of DiCillo’s innate understanding of the simultaneous joys and frustrations of filmmaking on a shoestring budget.

DiCillo began his career in the ’80s, working as a cinematographer on films like Jim Jarmusch’s Permanent Vacation and Stranger Than Paradise and Bette Gordon’s Variety, and was immersed in the indie boom of the early ’90s. Looking back on the era in a phone conversation with Decider, DiCillo observes, “It was such a different time. Because there was no doubt that if you made a movie, it was going to end up on a screen. If you were lucky enough to get a distributor there was no other venue for it at that time other than projecting it in theaters with an audience. There was a cycle, a rhythm to making a film, getting it released, that was very exciting… it was like this moment of non-Hollywood films having life.”

In 1991, DiCillo made his directorial debut with Johnny Suede, starring a then-unknown, baby-faced Brad Pitt as an aspiring ’50s-style rock star with a comically oversized pompadour. The director spent four years on Johnny Suede, but the film ultimately “didn’t make much of a splash.” Living in Oblivion “originated from one of the deepest, darkest periods of my early career,” DiCillo recalls. After Johnny Suede‘s lack of success, DiCillo had a moment of inspiration borne out of frustration: “I had another movie—which ended up being my third movie—Box of Moonlight, which I was trying to get money for and could not get made. In the interim, after three martinis at a party, I had this idea. Some guy came up to me who I had known from an acting class eight or nine years earlier. In my alcohol-vodka haze, this guy floats up and says, ‘Wow, Tom! So great to see you again, man! You made a movie! Lights, camera, action!’ And I was so pissed off that I had spent so many years trying to raise the money for just this one movie that I just said, ‘Oh just shut up, will ya?’ I said, ‘You don’t know the first thing about making a movie, how hard and tedious and frustrating it is. You can have an actress all ready to do a scene, and everything’s ready to go, it’s a scene you love—and at the last minute, someone drops the microphone into the shot.’ That’s when I got the idea, right then. That second. And I went home and wrote it, after my hangover wore off.”

“It’s an extremely personal film,” he continues. “I financed it by myself. I cast it with whoever I wanted. Anybody who wanted to be in the film and had a few dollars got a part.”

The film was originally a short: “The first half hour was literally shot in five days in black and white with that little touch of color in it, because I just thought that was the way it should work. It started out as a half-hour movie. Once we were done, everybody said, ‘Oh Tom, this turned out great! We should do something with it.'” The challenge of starting with a short led to the film’s novel structure, as DiCillo “was forced to try to do a part two and a part three that would somehow integrate seamlessly with what I had already shot. Several ideas then had to be decided, which was when to go back to black and white, when to go to color again. It was a really interesting challenge to try to use all the elements from the first half hour to create a feature.”

From there, the film’s unique structure emerged: parts one and two are dream sequence perspectives from director Nick Reve (Buscemi) and actress Nicole (Keener), respectively, on shooting the movie-within-a-movie, wherein everything goes amusingly off the rails. Part three concerns the shooting of a dream sequence, but in an ironic twist, it’s the only part of the film that is not a dream sequence itself. The film is a model of how to create a recognizable world on a small budget, and the three-part dream versus reality structure is absorbing and brisk (the film runs a cool 90 minutes). DiCillo’s real-world experience of indie film pitfalls is injected with a dose of surrealism that feels inviting rather than pretentious.

One of the film’s most memorable scenes comes in part three. Tito (Dinklage), an actor wearing a sky blue tuxedo and top hat, holds an apple just out of reach and walks around Nicole clad in a wedding dress. Tito quickly becomes annoyed by being used as a signifier of automatic quirkiness in a dream sequence, shouting “I don’t even have dreams with dwarves in them!” DiCillo says that casting Dinklage was one of the parts of the film of which he was most proud. “He had never done a movie when I cast him. He was a friend of Kevin Corrigan’s, who plays the AC who’s always stoned out of his mind. We were having trouble casting someone to play Peter’s part because I stupidly assumed that anybody under three feet tall could play that part. I realized, I’d actually written a part that required a really good actor. He said he knew this guy that worked in this fax shop in Brooklyn.” Dinklage came in and the rest was history.

DiCillo has a knack for spotting soon-to-be stars. Working with a low budget can be freeing. He says, “One of the things about casting is that if you don’t have enormous financial concerns—in other words, people breathing down your neck, saying, ‘You’ve got to cast so and so. We can get x amount of millions of dollars at the box office’—the next best thing is to cast whoever you want who is going to do an amazing job.” There has long been speculation that the amusingly named Chad Palomino (James LeGros) — a self-absorbed, pouting actor appearing in the movie-within-a-movie for artistic credibility — was based on Pitt, which DiCillo firmly denies.

“Brad had agreed to play the part himself,” DiCillo states, “but had to pull out due to publicity requirements for Legends of The Fall. This fact in itself should put the rumor to rest.”

He also remembers the fateful casting of Johnny Suede: “Brad was a challenge, in the sense that I couldn’t find the guy. I spent almost a year casting, trying to find someone to play that part. And I ended up going out to California to cast. He was on a list that my casting director brought in.” He had some small television roles and “one film about to be released called Thelma & Louise. No one had seen it. He came in, I took one look at him, and I said, ‘This is the guy.’ When he auditioned, I said, ‘This guy’s not only going to be in the movie, but he’s going to be a huge star.'” Even as Pitt’s profile started to rise at the last minutes of Johnny Suede‘s production, as Thelma & Louise started to take off, “He stayed faithful to me,” says DiCillo.

The writer/director felt that making Living in Oblivion a few short years later was “an exorcism, in a way.” He continues, “Especially on a low-budget movie, there’s great freedom, but there’s tremendous pressure. Because you have to get it. And if you don’t, you never get the chance to get it again. You don’t have the money to come back and reshoot the scene.” Buscemi’s performance is one of neurotic perfection, and DiCillo notes, “Most people think of independent directors as these cool people. But that’s never the case. Never. You’re always one inch away from complete hysteria, no matter how much control you have.”

The first part of the film, which takes place within Nick’s dream of a day on set, is an illuminating look at everything that can possibly go wrong during a shoot, from visible boom mics to unfocused shots to forgotten lines to spoiled milk on the craft services table, and Buscemi’s mounting frustration punctuated with moments of creative inspiration is endlessly entertaining to watch. Tellingly, the audience is never given much sense of what the movie-within-the-movie is really about, beyond the few scenes we see being filmed. “I just was always fascinated, from the very beginning, by what happens off-set. Just literally three inches away from what the camera is showing. I’ve found that, a lot of times, that drama is more interesting than what you’re trying to film,” notes DiCillo.

Having already dealt with the trials and tribulations of indie filmmaking, he says, “The fact that it turned into a comedy was just so therapeutic for me.” 25 years after its release, Living in Oblivion is both a time capsule of the mid-’90s indie world (the obviously David Lynch-inspired dream sequence of part three and Chad referencing that he just wants to work with Quentin Tarantino come to mind), and a refreshingly irreverent look at the labor of moviemaking, that comes from a place of love and frustration in equal measure. DiCillo expressed his annoyance with a contemporary review that called Living in Oblivion “a film about filmmaking that’s just for filmmakers.” That was hardly what he was going for, and the film has enough humor and style that it doesn’t feel that way to the audience. As DiCillo says, “It’s a human endeavor. It’s a group of people struggling to do something. That struggle is what really interests me.” 25 years later, DiCillo’s spot-on depiction of behind the scenes struggles remains a delight.

Abbey Bender is a New York-based writer with bylines in The Washington Post, The Village Voice, Nylon, Sight & Sound, and other publications.

Where to stream Living In Oblivion