Hulu’s High Fidelity usually sees the world, or at least its sliver of gentrified Brooklyn, from Zoë Kravitz’s perspective. Her schlubby chic character Rob is the one speaking directly to the camera, detailing her various heartbreaks, making all her top five lists, and riffing on the habits of the male Robs that came before her, whether in the John Cusack movie or Nick Hornby’s original novel. But where the previous iterations of High Fidelity were all Rob all the time, the TV series has the time and space to incorporate other perspectives: In episode eight, “Ballad of the Lonesome Loser,” Rob’s friend and colleague Simon takes over to monologue about his top-five heartbreaks.
Showrunners Sarah Kucserka and Veronica West had always intended to upend Rob’s perspective with a standalone episode during the later part of the show’s debut season, episode writer Solomon Georgio told Vulture, since that’s when Rob is acting especially gloomy and in the depths of self-sabotage. “We knew we were going to do the one-off episode of Simon’s top-five heartbreaks,” he said. “My pitch was that all of his 5 heartbreaks are the same guy, and that made the episode mine immediately.”
Over the course of the episode, Simon (David H. Holmes) reveals that he can’t stop getting entangled with a lawyer named Benjamin Young (Christian Coulson), whose particular brand of Brooklyn douchiness is signified by the fact that he insults Rob’s DJing ability, orders vodka sodas, insults Simon’s lack of ambition, and gives him chlamydia. “Ben is actually named after an ex of mine, but he’s nowhere near that character,” Georgio admitted. “It’s sewn together pieces of a lot of terrible guys. The guy who gave me chlamydia was a different person!”
For Holmes, the episode was a “cathartic” opportunity to develop his character. “Everybody has — it doesn’t matter gay or straight — that person where you look back and are like, Why was I with them for five years?” But in the process, he had to master the specific skill of talking to the camera in the way that Kravitz does in every other episode. “What they did, which Zoë really pushed for, was put the camera really close to me,” Holmes said of shooting the confessional scenes under the guidance of Jeffrey Reiner, who directed the episode. “If the camera is further back, you lose the intimacy. But once the camera was right there in your face, it was oddly comforting.”
Like Rob, whom Simon dated before he came out, most of Simon’s inner and outer monologues are about the things he likes, and especially the music he likes. For his episode, Georgio wrote dialogue that reflected the music he personally loved: In one scene, Simon and Ben hang out at a gay bar and listen to a drag queen attempt “It’s All Coming Back to Me Now” (“I just love that song, even if they make fun of it in the episode”), and in another, Simon launches into a defense of Sylvester and disco as “the sound of liberation,” given how the genre gave DJs at ’70s gay bars a say in which songs made it to the radio. “I grew up in Seattle as a music nerd in the ’90s,” Georgio said, “I’ve been obsessed with Sylvester since I was young.”
That monologue about Sylvester also served as Holmes’s audition for the show. “I was still working at a bar at the time, so I was running [that monologue] with regulars,” he said. “I wore a shirt for one of my favorite bands, Minor Threat, and the director of the pilot came up afterward and was like, That’s my favorite band, too.” When it came time to choose songs for Simon’s episode, the Minor Threat track “I Don’t Wanna Hear It” made the cut — an instance of the show writing the character to fit the actor’s interests. “A lot of the songs were made a little more punk,” as Georgio put it.
In contrast to Rob’s various romantic catastrophes, “Ballad of the Lonesome Loser” ends with hopefulness: Rather than let Benjamin back into his life yet again, Simon asks out the blond barista he’d been crushing on. It’s a bit of a twist: While Simon recites his heartbreaks with Ben, the episode follows him getting ready for a date, which we eventually realize is with the barista. He keeps looking for a formal shirt that Ben gave him — a slight misdirect that makes us think he’s going to choose Ben again — but when he can’t find it, he ends up wearing what Holmes jokingly called “the clown shirt.” It marks a definitive break from his past, even if it’s an extremely colorful (that is, not at all Simon) outfit. “That shirt’s like 300 dollars!” Holmes said. “I was appalled by the price of it, but I will say, it was very comfortable.”
Kucserka and West were the ones who suggested using the barista character as a counterpoint to Rob’s drama, though it’s not “all peaches and rainbows,” per Holmes. Simon’s new relationship ultimately forces him and Rob into a tense dynamic at the end of the season, where they have to acknowledge the way their romantic past clouds the closeness they pretend to take for granted. “I really loved when she confronts Simon’s character about why he left her, and he’s like, I never left you,” Georgio said. “It was great to see that platonicness of two exes, because so many people tend to ignore that.”