The ’90s were arguably Tommy Lee Jones’ best decade. The man just went from win to win, starring in Oliver Stone’s “JFK” in 1991 before earning an Academy Award for Best Supporting Actor just two years later for his role in “The Fugitive.” His turn as legendary Batman rogue Harvey Dent/Two Face in 1995’s “Batman Forever” might not have been everyone’s c’up of tea but for kids who grew up in the ’90s, Jones’ take on the character was our only reference, and he did a fine job as far as we’re concerned. Quintessential 90s disaster movie “Volcano,” “Men in Black,” “Under Siege,” “Natural Born Killers” — Jones was on a roll in the final decade of the millennium and, as such, it’s impressive he also managed to make his directorial debut with “The Good Old Boys.”

The same year he starred in “Forever” alongside Jim Carrey (whose buffoonery he simply couldn’t sanction) he also found time to adapt Elmer Kelton’s novel, in which he played conflicted cowboy Hewey Calloway — a man caught between his yearning for the open range and his love for schoolmarm Spring Renfro (Sissy Spacek). Calloway’s brother, Walter (Terry Kinney) has the kind of life that’s at complete odds with Hewey’s ideas of freedom. He’s settled with his family, Eve (Frances McDormand), and two sons, Tommy (Blayne Weaver) and Cotton (Matt Damon). Despite his yearning to break free, Hewey sticks around to help with the homestead out of a sense of duty, and pursue Spring in his off-time. But when his old pal Snort Yarnell (Sam Shepard) arrives, Hewey is tempted to embrace some bad habits from his past.

At the same time Tommy Lee Jones was at a career peak, Damon was just getting started. The young actor was yet to co-write his Academy Award-winning film “Good Will Hunting” and was living with his buddy Ben Affleck in Los Angeles. The pair had already been in a handful of productions, appearing as extras in Kevin Costner’s “Field of Dreams” back in 1989 before landing roles in 1992’s “School Ties.” As such, “The Good Old Boys” was a small but significant part for Damon, allowing him to continue working in the industry while preparing to pen his award-winning drama. It also planted the seed that wouldn’t fully bloom until 2010’s “True Grit.”

Speaking to RTE about “True Grit,” — which was a remake of the 1969 John Wayne-led original that became the blueprint for Wayne’s career — Matt Damon elaborated on his character, Texas Ranger LaBoeuf, saying:

“I worked with Tommy Lee Jones in 1994 when he directed ‘The Good Old Boys’, […] I had Tommy as a frame of reference [for ‘True Grit’] because he’s from West Texas. And he’s also somebody who is really fun to listen to, he knows a lot about a lot, and there’s something of the English teacher in him. You can ask him an obscure question and he enjoys knowing what he knows [laughs]. And so we kind of riffed on that. It’s not exact but it’s a similar way of presentation. My character in ‘True Grit’ is supposed to be a windbag, it’s like he comes over as a man who knows everything but actually doesn’t know very much at all! Not that Tommy’s like that, but Tommy is a great storyteller. And that was where we started to build the guy.”

It’s not the most flattering endorsement for Jones, but clearly “The Good Old Boys” meant more to Damon than a way to pay the bills — as it should. Aside from its impressive cast of current and soon-to-be Hollywood stars, the film was quite well-received. It isn’t one of the greatest Westerns ever made, but Variety’s Jonathan Taylor was impressed, noting how the ostensible “vanity project” “should be an indulgent and self-conscious effort; instead, it’s a work of uncommon charm and poignance.” Taylor even opined that while the film was made for TNT, it would “look just fine on the big screen.” Meanwhile, Sissy Spacek was nominated for a Primetime Emmy Award for Outstanding Supporting Actress in a Miniseries or a Movie.

Not only did Damon get a role in a well-reviewed TV movie, a paycheck, and a source of inspiration for his “True Grit” character, he also made the connection that might very well have secured his casting in the Coen brothers’ 2010 western. “I first met [co-director Joel Coen] in 1994 when I did a cable TV movie [‘The Good Old Boys’] with his wife Fran [Frances McDormand] down in West Texas,” explained Damon to RTE. “So I had met Joel in West Texas 16 years ago and it took them that long to offer me a job.”