‘Chasing Chasing Amy’ Tells How One Trans Man Found Truth in a 1997 Indie Flick

This article contains spoilers.

Everyone has a Chasing Amy.

The 1997 Ben Affleck-starrer was a successful, albeit controversial, indie flick directed by Kevin Smith that garnered a Golden Globe nomination for Joey Lauren Adams, who played Alyssa. In the film, she is an out lesbian comic book artist, and Affleck is a fellow artist who falls for her—sexual confusion and frustration follow.

The off-beat romantic comedy isn’t exactly the kind of movie that inspires fandoms in the style of Star Wars or Marvel. For a young Sav Rodgers, though, Chasing Amy was everything.

A decade after the then-12-year-old Rodgers discovered the movie, the filmmaker has completed his own feature-length documentary, Chasing Chasing Amy, which explores his life, journey, relationship to, and the complicated legacy of, his motion picture obsession. The doc premiered at Tribeca last month and will be the closing night film for Outfest on Sunday, July 23, in the historic Montalban Theatre in Hollywood.

Rodgers said that he “couldn’t have asked for more,” adding that audiences thus far have been “generous and engaged.”

It’s a unique task, unwinding a movie written and directed by a straight man about a lesbian. At the end of the now-26-year-old movie, Alyssa has a new girlfriend, but it is implied that Affleck’s Holden might have been the true love of her life.

This led many in the 1990s-era lesbian community to cry “foul,” arguing that the film was saying the right man can turn any woman. Alyssa’s own lesbian friend group has a similar reaction in the movie, and Rodger’s doc includes several talking heads that express those frustrations. It’s murky, to be clear.

Just a few years ago, when the movie turned 20, a barrage of think pieces hit the web, from BuzzFeed to The A.V. Club, evaluating the “Chasing Amy’s” legacy and what exactly it says about the queer community. From the lens of 2023, the character of Alyssa can be viewed as falling somewhere else on the sexual spectrum, and while other aspects certainly date the movie, her sexual fluidity might even be called progressive.

These are all angles discussed in the documentary, and it is at this intersection that Rodgers came to love—or rather consume—the movie. It was an outlet for him; an exploration of self. 

The Kansas native struggled for years to figure out who he was, but during the creation of Chasing Chasing Amy, Rodgers accepted himself as a trans man and began his transition. Prior to this, he had fallen in love with a lesbian woman, Riley, now Rodgers’ wife.

The documentary explores both of their unique paths through sexuality and gender—and unlike an endless chase for an Amy, they have instead secured their Amys. While a hilariously complex conclusion to Alyssa and Holden’s story can be found in “Jay and Silent Bob Reboot,” the documentary offers a more complete tale of what might come at the end of self-exploration. 

“Chasing Amy is a very specific thing for me,” Rodgers said. “And I think I'm the only one who can have this specific angle on the documentary.”

Chasing Chasing Amy began its life with a 2018 TED Talk, where Rodgers discussed the life-saving effect Smith's film had on him, and how he saw himself through the character of Alyssa.

“When marginalized people talk about the need for representation in media they are not hyperbolic,” Rodgers said in the TED Talk. “Seeing yourself on screen endows you with the feeling of existing in the world. And seeing myself on screen gave me the strength to navigate that world.”

The talk went viral and got the attention of Affleck and Smith, who reached out to Rodgers. Within a year, Rodgers was well on the path to making his own movie about his favorite movie, and he interviewed essentially every major player, minus Affleck, involved with the 1997 film for his documentary. Smith has already seen the completed product.

“Kevin and I talked on the phone for about an hour after he watched it with his mom for the first time, and it was this incredible career and life-affirming conversation,” Rodgers said. “How do you top the guy who made you want to be a filmmaker complimenting a film you made commentating on his film as being one of his favorite films about film? He also told me his favorite part was Riley, which, of course, is my favorite part too.”

The heart and soul of Rodgers’ story is certainly his own love story with Riley.

“Something that is so accidentally kind of radical about this movie is I keep the girl at the end,” he said. “How many movies do we get to see where a trans person is loved?”

While the central love story with Riley is a large part of the movie’s heart, it is the path to self-love that truly is the throughline for the film. As Rodgers unpacks the mixed messages of the source material and chronicles his life and love, viewers are given a window into how art can transform, even when the art itself might be imperfect and complicated.

Chasing Chasing Amy becomes an argument for the beauty, connectivity, and inherent worth of art’s subjectivity. Everyone has a Chasing Amy. Whether, back to the diva-worship of classic cinema and the likes Bette Davis and Marlene Dietrich, to the Trekkies to “Hocus Pocus” fanatics. Film, television, books, and perhaps even campfire tales give a window into who people are, who they want to be, and all of the possibilities therein. Obstinately about one movie and one trans man’s journey, the film aims to thread the human experience.

“Folks will tell me about the unlikely films that helped get them through a dark chapter in their life, or the incredible queer stories that have come about in recent years that are more directly made for LGBTQ+ audiences by LGBTQ+ storytellers,” Rodgers said of audiences’ connections with the films. “It's beautiful to hear the range of stories people have responded to that have made it a little easier for them to be themselves.”

In another 20-odd years, if another young filmmaker is evaluating his movie, perhaps in something like a “Chasing Chasing Chasing Amy,” Rodgers hopes that his documentary can be viewed as a further window into progress.

“All I can really hope for is that it still somehow resonates with people because we were able to capture something universal or timeless in the story's specificity,” he said. “I hope we can look back and measure how much progress we've made as a society, or how language has evolved, or how we've all changed using the media as markers. I hope that we can learn from what has worked, leave what hasn't, and make new films that imagine what our future can be. I also hope we can make movies that dare to dream of a better future for everybody, rather than simply holding a mirror up to the worst of our current reality.”

For information about the film and future screenings, visit chasingamydoc.com.