There will come a seemingly ordinary Wednesday night when you discover something. Flicking through movies to watch on your Fire Stick, your eyes will widen seeing something called The Comeback Trail starring Robert De Niro, Tommy Lee Jones, and Morgan Freeman. The trailer for it doesn’t look good, but it’s also clearly got more production value and polish than direct-to-video Randall Emmett movies De Niro and Freeman have appeared in. What is this movie? Where did it come from? How could something with so many stars basically vanish?
Believe it or not, the movie that will stand out on that mundane Wednesday night has a saga behind it. It’s taken years for a critically derided comedy like The Comeback Trail to come to North American audiences. Director George Gallo, a veteran of post-2015 DTV Redbox Entertainment and Grindstone Entertainment titles, began shooting The Comeback Trail back in summer 2019. Yes, that makes Trail a rare movie to shoot before COVID-19 (along with the still unreleased Kung Fury 2) that didn’t hit American theaters until the mid-2020s. This production focused on a weaselly producer, Max Barber (Robert De Niro), who desperately needs to pay off mobster Reggie Fontaine (Morgan Freeman). Discovering an incident where a movie star’s death gives another producer millions of dollars, Barber gets an idea. He’ll take ancient movie star Duke Montana (Tommy Lee Jones), put him in a Western, and kill him through a “stunt gone wrong” that will give him an insurance settlement big enough to solve all his money woes.
At the time, this feature was clearly meant to capitalize on a string of geriatric comedies like Last Vegas, Dirty Grandpa, and Going in Style all clogging up theaters. The Comeback Trail was meant to differentiate itself from that crowded pack of features by emphasizing Western imagery and lots of showbiz satire. There were almost certainly plans to launch it in 2020 … and then COVID-19 shut down theaters.
This was the beginning of The Comeback Trail’s bizarrely protracted journey to getting released in North America. Initially, though, things looked hunky-dory. In June 2020, distributor Cloudburst Entertainment picked up domestic rights to The Comeback Trail and planned to launch it in theaters that holiday season. Cloudburst Entertainment was started by a former Pure Flix executive as a kind of successor to that company. Picking up The Comeback Trail for a November 13, 2020 debut indicated that Cloudburst had more star-studded aspirations for distributing movies than just handling more God’s Not Dead sequels.
Just a few days before its planned release date (and weeks after it premiered at a Monte Carlo film festival), Cloudburst delayed Trail’s release to 2021. The lack of open movie theaters and the reluctance of older audiences to come out to multiplexes during an ongoing pandemic were the reasons for the postponement. Eventually, a July 23, 2021, release date was selected, though this, too, would get scuttled at the last minute (this was around the time that this site reviewed the film). The rest of the world, though, wasn’t waiting for the U.S. to watch The Comeback Trail. A handful of European territories (plus Australia and Brazil) already got the title in late 2020. Most other territories would get The Comeback Trail in movie theaters between July and October 2021.
The Comeback Trail even debuted on streaming in the United Kingdom through the Sky Cinema streaming service in June 2021. These kinds of releases may have been the ultimate kiss of death for The Comeback Trail’s domestic theatrical run. Because the film was already available in numerous countries on physical and digital media, American distributors may have feared that audiences could access it through piracy or foreign releases. Cloudburst basically ceasing functions as a full-time distributor also didn’t help matters. The Comeback Trail had gone cold and would remain that way for eons to come.
In the years that followed, no further updates emerged on The Comeback Trail. Due to the film’s obscurity and lack of connection to popular franchises, De Niro and Freeman were rarely asked about its status during press interviews. Occasional reminders of its existence would creep out from the ether, like its official soundtrack inexplicably dropping in August 2022. In November 2023, critic Nathan Rabin covered the film on his site, which was about the extent of publicity The Comeback Trail received in that entire year in North America
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Hollywood’s hesitancy to even make in-house comedies (let alone acquire them from independent vendors) likely had something to do with The Comeback Trail languishing in obscurity for so long. Another simple problem was just that the movie had received terrible reviews from audiences who’d seen it. Rather than being some cult gem major studios were too square to get, The Comeback Trail (a remake starring beloved actors that had headlined a turkey or two in their time) had all the makings of something that would sink like a stone once word-of-mouth set in. Who wanted to take a chance on that?
It didn’t help that the feature was already weirdly dated in some respects the longer it sat on a shelf. For one thing, the geriatric comedy phase of the 2010s had long faded into obscurity. If senior citizens were headlining theatrical yukfests now, they were mimicking Book Club not The Bucket List and Last Vegas. A more nitpicky instance of outdated material was a key joke in early trailers centered on the director of The Comeback Trail’s in-universe doomed Western movie. Megan Albert (Kate Katzman) applies for the gig and Duke Montana immediately takes a liking to her. When Barber’s nephew Walter (Zach Braff) protests, saying that they need a director “with masculine energy,” Montana fires his gun in the air to threaten his cohorts into giving Albert the job.
The gag here is that Montana is “crazy” enough to make Barber and company do anything, including letting a LADY direct a Western. That tired joke built on gender essentialism was always nonsensical since Kelly Reichardt, Lina Wertmuller, and Antonia Bird (among many others) have all directed acclaimed Westerns. However, since The Comeback Trail started shooting, Jane Campion wrote and directed 2021’s The Power of the Dog, a Western with a largely male cast that scored her a Best Director Oscar. Having a joke that functioned as a relic on so many levels likely further alienated The Comeback Trail from any domestic desaturates. Who wants a comedy with jokes that feel so out of touch with reality?
The sad, prolonged tale of The Comeback Trail’s journey to getting domestic distribution abruptly came to an end in February 2025. Out of nowhere, the film was set for a simultaneous theatrical and premium video-on-demand release for February 21. This debut was given so little fanfare that a proper new American trailer for The Comeback Trail only dropped nine days before its February 21 bow. Now being unceremoniously unleashed to domestic audiences by Variance Films, the tortured saga of The Comeback Trail’s American debut will undoubtedly overshadow the critically panned movie itself. Not every cowboy rides off into the sunset. Not every joke is greeted with uproarious laughter. And not every movie (no matter how star-studded it is) gets an easy ride to theaters.
