Living in Oblivion is a hilarious film for anyone who has created, worked on, or loved watching independent films. Low-budget movies are made with high hopes and passion, with the participants often working for little-to-no pay. Everyone is there to help fulfill the director’s vision. The process of creation is fueled by anxiety. Director Tom DiCillo made Living in Oblivion after his feature debut, Johnny Suede, bombed in a very brief theatrical run. This film, celebrating its 25th anniversary this year, is DiCillo’s absurdist ode to the indie-filmmaking experience.
Living in Oblivion is a film in three parts, each of them depicting anxiety-dream sequences. The first is from the director’s perspective. Steve Buscemi embodies the frazzled Nick Reve with humor and aplomb. At first, Nick seems very on the ball, but Murphy’s Law keeps infecting the set. One thing goes wrong after another, causing Nick to eventually lose it.
The scene being shot is about trying to get a take in which the lead actress, Nicole (Catherine Keener) discusses, in character, how she was abused by her father while her mother did nothing. That is just the plot of the film-within-the-film. Cora (Rica Martens) is the actress portraying her mother.
I won’t spoil everything that goes wrong in each of these anxiety dreams, because there are so many incidents I want you to discover for yourself. A brief list of mishaps during this sequence: trouble with the boom mic, focus problems, a distraction from Nicole’s end that rattles her, and Cora saying the wrong line. Finally, Cora makes a connection with Nicole that makes the two actresses perform the scene to perfection. But it just so happens that the director of photography, Wolf (Dermot Mulroney), is in the bathroom getting sick from spoiled milk in his coffee. There’s not a huge budget for craft services (food) on this film shoot.
Nick goes crazy and blows up at everyone present on the set. There’s a beeping noise that confounds him and compounds his mania. The beeping noise turns out to be an alarm, and he awakes, starting the second segment of the film.
I take you now to the actress’s anxiety dream. Nicole wakes up in a hotel room with her co-star for the coming day. She does not look thrilled. Her co-star is Chad Palomino (James LeGros). You know there are actors like Palomino, guys who have been overpraised so much that they think they can control any set, give awful and sometimes pretentious advice to anyone on the set, and are basically just himbos without much actual talent. The scene they are shooting is about the female character admitting she has romantic feelings for the male character. It’s clear during take after take that Nicole can’t stand Chad in real life, but Chad keeps plugging away, making one horrible acting choice after another. Chad begins to progressively irritate every male crew member in the room and come on to every female crew member. The tension escalates to a point where an actual physical fight scene involving Chad, Nick, Nicole, and Wolf breaks out to appropriately amusing results.
Nicole’s alarm clock wakes her out of her anxiety dream into the third segment: her film character’s anxiety dream. This popular trope in independent films is outrageously spoofed in this one. Nicole’s character, Ellen, is wearing a wedding dress in an empty room. In walks Peter Dinklage playing the character Tito, clad in a powder-blue tuxedo and top hat. He circles her while holding out an apple that she can’t quite grab. Again, many takes go wrong because of various mishaps. Tito’s frustration and anger finally crescendos into an uproarious rant about the cliche of using dwarves in dream sequences. He makes a great point and convinces Nick of that fact. Nick’s breakdown in this segment leads him to actually want to stop shooting his film. An actress who was in the first segment who winds up playing a completely different character in this one gives this farce of a scene a resolution that gives back all hope to Nick.
There is a brief coda at the end of Living in Oblivion comprised of daydream sequences of various cast and crew members. Each one is hilarious and a perfect completion to a film based on anxiety dreams.
DiCillo did a masterful job of showing the world what it is like on a low-budget indie film. A lot of his movie was autobiographical. Because of that, many misinterpreted that the shallow Chad Palomino character was based on Brad Pitt. DiCillo confirms that this is not true. Apparently, Pitt, who starred in his first film, Johnny Suede, was supposed to play the part of Chad Palomino up until the time the shooting of Living in Oblivion was about to start. Pitt couldn’t break the contract with another project he was on, so James LeGros was brought in at the last minute. 
Interestingly, almost all of the actors in the film invested in the project. The first to be involved were Catherine Keener and Dermot Mulroney, who were married at the time in real life. The only character that auditions were held for was Tito, and it turned out to be a fantastic film debut for Peter Dinklage. 
The way DiCillo shot this film was very unique. The first segment was shot in 16mm black-and-white, but every time that they were shooting the film-within-the-film, it was shot in 35mm color. For the second and third segments, the behind-the-scenes shots were in color, while the film-within-the-film footage was black-and-white.
I can’t stress enough how hilarious this film is, and I was so tempted to give away a lot of the dialogue and action. Comedy this precise needs the element of surprise, and I want to let you have the experience. Not only is Living in Oblivion one of the funniest films about filmmaking, it’s also pretty accurate. From interpersonal relationships gone sour to equipment malfunctions, it displays what can and often do go wrong on sets. Warning: some independent filmmakers consider this as their version of This is Spinal Tap, but like that movie is to rock stars, this is a must-see for directors, producers, and actors on low-budget projects.
  Living in Oblivion DVD, director’s commentary, Sony Pictures Classics