Based on English writer Nick Hornby's 1995 book, High Fidelity touched a nerve for music nerds everywhere when it was released in the heady days of Y2K. Director Stephen Frears transplants the protagonist Rob Gordon (Rob Fleming in the book) from swanky London to Chicago; where Rob (John Cusack) is a neurotic man in his late 20s, aimlessly running a record shop called Championship Vinyl. Rob is also going through a traumatic breakup with his longtime girlfriend Laura (Iben Hjejle) and dealing with his two inept employees at the struggling store: the quiet, awkward Dick (Todd Louiso) and boisterous, opinionated Barry (Jack Black.)

The movie's soundtrack is a music lover's dream; with everything from De La Soul to Beta Band to Stevie Wonder. The record store setting is an opportunity to showcase the characters' obsessive music nerdiness, and the rest of the film offers ample opportunities for director Frears to flex his. One way that Rob has opted to cope with losing Laura to an oily-haired middle aged gigolo named Ian aka Ray (Tim Robbins) is by "counting down" Rob's "Top Five Breakups." Bruce Springsteen, himself no stranger to mining lovelorn angst, comes to Rob in a dream and tells him that revisiting the worst breakups of his life will teach him something about himself and help him move forward. Rob proceeds to single them all out; almost defiantly excluding Laura. At first.

Rob met Charlie (Catherine Zeta-Jones) when he was an insecure college student, (as opposed to the insecure late twentysomething man he's become), and she was his smart, sophisticated and uber-sexy dream girl. Charlie dumped Rob for a galoot named Marco, and young Rob was devastated by the loss. As part of his "Top Five" approach to clearing his mental Rolodex, Rob phones Charlie, who subsequently invites him to a dinner party she's hosting—on the condition that he assures her that he's not going through "one of those what does it all mean? things."

Rob shows up for Charlie's party and Frears sets things well: the late 20s version of Charlie is a vision; effervescent and glowing when she comes to the door to greet Rob. And he soundtracks the scene with Eric B. & Rakim's 1992 track "What's On Your Mind," as Rob joins the party and soaks in the vapid WASPiness of it all. These are good-looking, trendy people having smart, informed conversations, and as he claims via first-person narration that he's "not a class warrior," Rob also admits that he does not fit in here.

Though not on the official High Fidelity soundtrack, "What's On Your Mind?" had already been prominently featured on a major soundtrack prior to its use here. The track first appeared officially in 1991's House Party 2, before its inclusion on Eric B. & Rakim's final album (to date) Don't Sweat The Technique a year later. Hardcore Hip-Hop purists may have decried Eric B. & Rakim's foray into more R&B-friendly territory, but the song is one of the duo's most prominent love tracks; and "What's On Your Mind?" flies in the face of Rakim's reputation as a rapper who only raps about rapping. Of course, it's not an entirely unprecedented moment in Eric B. & Rakim's discography: "Mahogany," arguably their most famous love song, appeared on 1990s seminal Let the Rhythm Hit 'Em. But "...On Your Mind" remains one of Rakim's most romantic endeavors, and the song glides over a flip of Midnight Star's 1984 classic "Curious," a track that would be famously sampled once again for LSG's 1998 hit "Serious" with MC Lyte, LL COOL J and Busta Rhymes.

And Eric B. & Rakim's work is again highlighted later in High Fidelity: when Ian aka Ray shows up at Championship Vinyl to issue a semi-warning about Rob's ongoing late-night calls and harassment of Laura. As Ian aka Ray offers passive-aggressive, quasi-positive dudespeak to diffuse the hostilities between the two; a seething Rob fantasizes about jumping his romantic rival with Dick and Barry lending a hand, as Eric and Ra's classic "Juice (Know The Ledge)" provides the fight music.

The Charlie scene in High Fidelity illustrates for Rob how we can often idealize certain people in our past—especially former lovers. But our love for them comes from a specific time and place in our lives, and nostalgia can be a sentimental liar. As Rakim kicks bars about getting next to his ideal woman, Rob is forced to confront the reality that no one is ideal. That's pretty high-minded assessment of a brief scene, undoubtedly, but it was definitely on my mind.