DiCillo has never had any trouble attracting talented actors to his projects. He has collaborated with Steve Buscemi, Catherine Keener, Dermot Mulroney, Brad Pitt, Sam Rockwell and John Turturro -- but finding investors has been a lot trickier.
Before directing his first feature, "Johnny Suede" (1991), DiCillo served as cinematographer on several '80s films, including three projects with independent filmmaker Jim Jarmusch -- "Coffee and Cigarettes" (1986), "Stranger than Paradise" (1984) and "Permanent Vacation" (1982).
"Johnny Suede" starred Pitt as a would-be pop singer and featured Keener in the first of four films she eventually made with DiCillo. In 1995, Keener co-starred with Buscemi and Mulroney in "Living in Oblivion," a profane comedy about the ups and downs -- mostly the downs -- of independent, shoestring-budget filmmaking.
Keener joined Turturro and Rockwell in the cast of the 1996 comedy-drama "Box of Moon Light," about an electrical engineer facing a midlife crisis (Turturro) who takes a detour from his routine life to kill some quality time with a nonconformist (Rockwell). She was also part of the ensemble in 1997's "The Real Blonde" -- starring Matthew Modine in the story of a struggling New York actor.
While his stars have largely gone on to establish themselves as in-demand feature film actors, DiCillo is still trying to set up a follow-up to 2001's "Double Whammy" -- starring Dennis Leary as a police officer who struggles with his failure to stop a massacre at a fast-food restaurant.
Moviegoers never got to see that one, because DiCillo didn't manage to snag a distribution deal for it.
"I don't know if demoralizing is the right word," said DiCillo in an interview with United Press International, "but it makes you draw deeper and deeper into your own sense of belief and finding, really, that love of why you're doing it -- because it's hard."
As he promoted the DVD release of "Living in Oblivion," DiCillo said that the distribution snafu for his last film was just the latest in a series of personal and professional disappointments.
"What can you do?" he said. "Just keep going. I'm not going to let the idiots win."
All kinds of obstacles can get in the way of a film project. DiCillo recalled that during the making of "Johnny Suede," someone stole all of Pitt's costumes.
"We had to hire a seamstress to remake the clothes, and they weren't an identical match," he said. "I was only hoping that no one would notice."
That's nothing compared to the kinds of problems that the characters in "Living in Oblivion" encounter as they try to shoot an independent movie-within-a-movie. Buscemi stars as the director, whose enthusiasm for the movie he is directing is sorely tested by faulty equipment, lack of time and a neurotic cast and crew.
"This business attracts some of the most neurotic people of any business," said DiCillo. "I actually fired a cinematographer once because the shots were out of focus -- and he finally broke down in tears and confessed he was intentionally sabotaging my film because he was jealous of me."
DiCillo said a main reason he made "Living in Oblivion" was to deflate the myth that independent filmmaking is some kind of idyllic alternative to high-pressure studio projects.
"The myth is that everybody's standing around looking cool, smoking a cigarette," he said. " In reality, most of the time they're running around like crazy."
The movie is funny despite an undercurrent of anger and hostility that DiCillo said was a reflection of his own life at the time.
"The film came out of a very dark period in my life," he said. "I had a choice -- should it be only about embitterment, or should it be about hope? I opted for the side of hope."
Once he gets financing in place, DiCillo's next project is a comedy he hopes Buscemi will star in.
"It's about a New York City paparazzi who hooks up with a young homeless kid -- they have a relationship like 'Midnight Cowboy,'" said DiCillo. "It's about their experiences on the fringes of the world of celebrities."
To keep body and soul together, DiCillo picks up occasional writing assignments and tries to live frugally with his wife in New York.
"I've done a few commercials," he said. "I wouldn't do just anything -- just things that I wouldn't feel like a total idiot doing."
But with the economy in a slump, movie financing is harder than usual to come by.
"My wife looks at me and says, 'Tom, when do you think you'll get your next job?'" said DiCillo. "She's been enormously supportive over the last 25 years. Maybe it would be good to go get a job somewhere."