George Gallo and Joy Hurwitz discuss their years-in-the-making Hollywood satire ‘The Comeback Trail’

“The Comeback Trail” may mercilessly satirize Hollywood and its sleazy duplicitous hustlers, but nevertheless, the new film’s backstory is something of a fairy tale.

The movie, which plays the virtual Aspen Filmfest beginning Saturday, stars Robert De Niro and reunites him with “Midnight Run” screenwriter George Gallo, who directs.

De Niro plays a down-on-his-luck producer of schlocky ’70s movies, who hatches a plot to have an old western star (Tommy Lee Jones) killed on his film set so that he can collect insurance money to pay off a debt to a mob boss (Morgan Freeman). Zach Braff co-stars as De Niro’s nephew and producing partner, Emile Hirsch as a slick A-list producer and their sometime rival.

The project’s roots go back to Gallo’s teen years in the mid 1970s, when the film is set. At a comic book convention in a Manhattan hotel, the young Gallo stumbled into a small rough cut screening of director Harry Hurwitz’s “The Comeback Trail.” The little-seen cult film and its concept stayed with Gallo as he grew up and began making movies himself.

“I kept thinking the idea for this movie is terrific, they’re trying to kill an actor for the insurance, and it stuck with me for years and years,” Gallo recalled this week in a video interview from Los Angeles.

As he built his career as a writer, director and producer with hits like “Bad Boys” to his credit, Gallo set his sights on remaking “The Comeback Trail.” For years he had attempted to obtain the rights, to no avail.

His luck changed around 2003 when he attended a private screening of “Midnight Run” at a friend’s house and there met Joy Hurwitz, widow to Harry Hurwitz and gatekeeper to “The Comeback Trail.”

“George’s eyes got really big and he said, “I want to remake ‘The Comeback Trail!’” Hurwitz, a producer on the remake, recalled in the video chat. “I said, ‘Remake it!’ And that’s how it began.”

Of course, nothing is as simple as that in Hollywood. The remake went through years of development with roadblock and hiccups at seemingly every turn.

The original Harry Hurwitz “Comeback Trail” is something of an underground Hollywood legend. Largely improvised, starring Chuck McCann and Buster Crabbe, it was a passion project for Hurwitz. Made for a budget of just $117,000, he conceived it as a fun thing to tinker with between other films.

“When you make independent films and do it for the love, there is this malaise after the last day of a movie,” Joy Hurwitz explained. “So they came up with ‘The Comeback Trail.’ … Every year they’d print a negative and go into the editing room and work on it.”

Filmed in 1974 and shown in a few theaters in 1982, it never received a proper release. Film prints of seven different cuts circulated around the film industry, including one owned by Playboy founder Hugh Hefner (he has a small cameo in the film and Hurwitz paid him with a film print). Hefner loved “The Comeback Trail” and screened it regularly at the Playboy Mansion, which gave it a cult following among the Hollywood elite.

“He played it at the mansion for years,” Joy Hurwitz recalled. “So there were all these producers in Hollywood who would quote it all the time, even though it was never finished and never released.”

Gallo’s long-developing remake finally got legs just a few years ago, when he was talking to De Niro when the actor was deep in production on Martin Scorsese’s grim gangster picture “The Irishman.”

“He said, ‘I’ve been playing a psychopath for eight months, I’ve got to wash this guy out of my system. Do you have anything funny?’” Gallo recalled. “I said, ‘Yeah, I’ve got something ludicrous.’”

He sent De Niro the script for “The Comeback Trail” and two days later De Niro was on board. From there, after years of false starts, the movie came together with Freeman and Jones quickly signing on.

“It all came together in a week, but it took 17 years to get to that week,” Gallo recalled with a laugh.

The film has picked up promising pre-release buzz, its trailer has gotten some 3 million views and it’s begun playing film festivals this month and has all the indications of a pending hit. But the coronavirus pandemic has its theatrical release in limbo.

“Now, with COVID and theaters closed, it’s like, ‘Well, of course this is going to happen to ‘The Comeback Trail,’” Hurwitz said. “Everything has been difficult.”

Everything except for the 27 days on the Albuquerque set, both Gallo and Hurwitz said. That was smooth sailing and fun.

Making movies about movies is always a treat for film professionals, and the veteran actors in the film took great joy in sending up the sleazy C-list filmmakers of the early 1970s (Gallo noted that they all knew these figures in those days). Gallo cultivated a loose and fun set that allowed the three Oscar winners on the top of the bill to enjoy the ride.

“It is unadulterated silliness,” Gallo said. “So we just had a good time. We all kept saying, ‘Let’s have a good time, let’s not take it too seriously.’” Near the end of the shoot, Gallo recalled, De Niro remarked “I haven’t had this much fun in a long time. It didn’t feel like work.”

Still, despite some of the cartoonish physical comedy and the ridiculousness of the plot on “The Comeback Trail,” De Niro and Freeman and Jones brought their best and their competitive spirit.

“You put three great actors together and the interesting thing they do is they know the others are terrific and they don’t want to get out-acted by anybody,” Gallo said. “So they are especially sharp. It’s almost like, ‘I’m not going to let him steal this scene from me,’ which is fun to watch, this healthy competition.”

atravers@aspentimes.com