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For a large cohort of male movie fans of a certain age, interpretations of the 2000 comedy High Fidelity have probably changed a great deal over time.

Many guys who were fans of the film, which marks its 20th anniversary this week, likely related at first to John Cusack’s Rob Gordon character. He was, after all, a pop culture obsessive who’s constantly making lists, related to both songs and women. He also, like a lot of us, had a checkered romantic history and was dumbfounded as to how to relate to the women in his life.

In subsequent viewings of High Fidelity, as we’ve gotten older and wiser, many of us— while still enjoying and appreciating the film— have belatedly come to the conclusion that Rob Gordon was kind of an ass. Much temptation as there was to compare Rob to Lloyd Dobler, the legendary teenaged romantic hero Cusack played in 1989’s Say Anything, the comparison in hindsight was less than apt.

High Fidelity, released in March of 2000, was directed by Stephen Frears, written by Cusack and three co-writers, and was adapted from the 1995 novel of the same name by Nick Hornby. The movie moved the action from London to Cusack’s hometown of Chicago but otherwise mostly followed the plot of the novel.

Rob Gordon is the owner of a record store, where he banters all day with his employees, boorish music snob Barry (Jack Black) and the more soft-spoken Dick (Todd Louiso.) Dumped at the beginning of the film by lawyer Laura (Danish actress Iben Hjejle), Rob seeks to explore the origins of his struggles with women, and therefore re-connects with his “top five” exes, played by the likes of Catherine Zeta-Jones, Lili Taylor, and Joelle Carter.

The Rob character, even by the most charitable interpretation, is self-centered and inconsiderate, and it’s a wonder any of these beautiful and interesting women ever gave him the time of day.

Sure, the ending hints at some newfound maturity and growth on the character’s part, but overall, if someone you knew engaged in a quest to seek out all their ex-girlfriends for purely self-aggrandizing reasons, you’d likely try to talk them out of doing so weird. Plus, like a long list of movies from that time period like American Beauty and Fight Club, the entire plot of High Fidelity could’ve been sidestepped if only the main character had gone to see a good therapist instead.

The wonderful but little-seen 2018 film Juliet, Naked was also based on a Hornby novel, but turned things around a bit: The music hipster character (played by Chris O’Dowd) is depicted not as the hero but rather as a selfish jerk, who’s awful to his girlfriend (Rose Byrne) and ends up losing her to his favorite musician (Ethan Hawke.)

High Fidelity, though, does all the little things right. The dialogue is uniformly hilarious, the musical choices all wonderful, and the Jack Black performance essentially launched his career as a movie star. I could watch Black’s character and his band, Sonic Death Monkey, sing “Let’s Get It On” over and over again.

The film has been a cable TV staple for two decades, and this year, High Fidelity inspired a ten-episode TV remake, on Hulu. The series, which was middling but showed flashes of brilliance, made Rob female, biracial and bisexual, and cast Zoe Kravitz – whose mother, Lisa Bonet, played a Rob conquest in the movie- in the lead role.

The Hulu show was set in Brooklyn, but perhaps owing to the potent power of musical hipsterdom, Rob remains a record store owner, with the Barry character now a black woman (Dolemite Is My Name‘s Da’Vine Joy Randolph) and the Dick character now a gay man (David H. Holmes).

Sure, the High Fidelity TV series was probably too long by two or three episodes, but Kravitz was so charismatic in the lead role that it was certainly never boring, and the show also made even more ambitious musical choices than the film. Though both ended with the same tune, Stevie Wonder’s “I Believe.”

John Cusack has said many times over the years that his portrayal of Lloyd Dobler made things harder for the young men of the era, since they could never measure to him. In the last 20 years, many men have discovered that they should never try to measure up to Rob Gordon.