The album may or may not be obsolete, but the fact remains: Listeners have long obsessed over individual songs. The Single File is The A.V. Club’s look at the deep cuts, detours, experiments, and anthems that make us reach for replay.

It’s rare that Dr. Dre and I set out on parallel quests. We come from different generations and socioeconomic backgrounds, and we don’t really run in the same circles. But for one weekend in the fall of 1999, we were fellow riders—he in a ’64 Chevy, me in an ’86 Nissan Sentra, both of us cruising toward the same foolish goal we’d never reach: We wanted to go back in time.

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I only wanted to rewind life six months, back to the tail end of my senior year in high school, before I left for college and the girl I’d been dating for two years rolled up on my heart with an AK and opened fire.

Dre’s mission was more ambitious: He wanted to go back to 1992. That was the year he dropped The Chronic, the game-changing album that made South Central gangsta living sexy to Middle America. Since parting ways with Death Row Records in 1996, Dre had kept rather quiet, and in the lead-up to his long-awaited sophomore effort, 2001, which was released in November 1999, fans were starting to whisper about whether he was still relevant.

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The idea that Dre was yesterday’s news wasn’t lost on the man himself. In the first verse of 2001’s leadoff single, “Still D.R.E.”—which hit radio in October 1999, right around the time I slumped onto a Greyhound bus and made my first trip home to suburban Hartford, Connecticut, from Boston University—he addressed the criticism head-on:

“Ladies, they pay homage, but haters say Dre fell off,” he raps. “How, nigga? My last album was The Chronic.”

On the surface, those words smack of defiance and bravado—traits for which the good doctor was certainly known—but listen closely, and Dre sounds like a guy unsure of where he stands. He’s making the shaky argument that he’s still a vital producer and rapper, because the album he dropped nearly a decade prior was so great. Elsewhere on the track, he goes to great lengths to convince the listener—and himself—it’s still the nine-deuce. He talks about weed and khaki suits and lowriders, as if nary a G thang has changed since The Chronic hit.

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It’s all right there in the opening lines, as former sidekick Snoop Dogg raps, “Still Snoop Dogg and D-R-E,” celebrating stasis and consistency in a way that feels completely foreign for hip-hop, a genre that’s always prided itself on evolution.

Dre and Snoop are inventing ’90s nostalgia before the decade is even out, and their reunion creates a warm and fuzzy feeling—or at least it did for me that first weekend home from college. As a middle schooler, I’d loved The Chronic for the beats and bad language and cinematic descriptions of drugs and violence. To a 12-year-old kid, it was like a big audio comic book, and Dre and Snoop were Batman and Robin, heroes to vibe with on my Walkman while doing my paper route.

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By 1999, my tastes had gravitated toward Elvis Costello and The Clash, but I still had plenty of love for Dre, and when I first heard “Still D.R.E.,” it felt weirdly comforting. The first weekend back from BU was like that chapter in All Quiet On The Western Front where the protagonist, Paul Bäumer, returns home from the front and can’t relate to anyone in civilian life. Up in Boston, I wasn’t subjected to intense shelling or trench warfare, and I never once heard the squeal of massacred horses, but the cocktail of academic stress and heartache was a nasty one. Back in my hometown, I was surrounded by reminders of how much happier I’d been in high school.

“Since the last time you heard from me I lost some friends / Well, hell, me and Snoop, we dipping again,” Dre raps later in “Still D.R.E.” and this gave me even more reassurance. That line about lost friends was about Dre’s NWA co-founder Eazy-E, who died of AIDS in 1995, before the feuding former homeys were able to squash their longstanding beef, but I could relate. Some of my old buddies had stayed friends with my ex-girlfriend and even visited her at her college, and because I was too immature to understand why this was okay—“bros before hos” is some ignorant bullshit even when you’re 18—I more or less cut them out of my life. But if Dre and Snoop could go “dipping again,” I could man up and extend a few olive branches. If nothing else, I could hit the streets in my Sentra with the radio loud and try to feel as good as I used to.

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Sonically, “Still D.R.E.” flies in the face of Dre’s lyrics. In the opening verse, he tells us, “It’s still Dre Day,” but the song sounds nothing like “Dre Day,” one of his smash hits from The Chronic. That song was all laid-back G-funk, a stoned-out diss track aimed at Eazy and anyone not down with Dre and Snoop and their hazy brand of nihilistic hip-hop. With its omnipresent piano and pizzicato-string loop, “Still D.R.E.” is anxious and urgent. It suggests the kind of paranoia felt by novice tokers who can’t hold their smoke—not the cool buzz of a couple seasoned pros like Dre and Snoop. The music seals the deal: This ain’t the early ’90s, and it never will be again.

In the end, Dre’s failure to recreate 1992 was as fortuitous as my inability to win back that ex. The 2001 album proved a major hit—it’s sold even more copies than The Chronic—and on the whole, it succeeds on far more than just nostalgia. Far from G-funk redux, it proved that any insecurity Dre felt was unwarranted. He could still innovate, and in subsequent years, he’s produced hits for the likes of Eminem, 50 Cent, and Alicia Keys. He’s also made a fortune with his Beats By Dre headphones, and if he ever drops Detox, the follow-up to 2001 he’s been promising since, like, 2001, he’ll probably blow the minds of the collective public once again.

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Dre’s not a legacy artist, in other words, and he doesn’t have to play the “remember me?” rap circuit. He may no longer be hitting the corners in his lo-los with Snoop, but he’s not a 27-year-old guy acclimating to superstardom. Things change, and he’s had new adventures. The same goes for a certain Connecticut kid—now happily married, just like that ex, and glad as hell high school is over—who once took solace in one of his greatest, most misguided songs.