INTERVIEWS125 Best Albums of the Past 25 Years

25-year-old Missy Elliott had already lent her hitmaking skills to Aaliyah by the time Supa Dupa Fly dropped, produced and recorded by the massively influential Timbaland. The album was a big bang for the music that followed in its meteoric path. "Missy and Timbaland expanded the boundaries of hip-hop — the sound, the look, even the perspective," SPIN wrote in 1998. Her celebrated eccentricity kept her close to another offbeat hip-hop hero: Busta Rhymes. "It's like we're both these loud characters," she told SPIN in 1998, "but we're also sort of unexplainable, you know what I mean?"

LL Cool J introduced himself rather impressively in 1985 with Radio, a debut album that would go on to be known as "a serious jam." Rap tracks with uniquely strong song structures would help establish Radio as a formative hip-hop classic, and the way it caught on seeded the idea of rap crossing over into the humongous scale of rock. SPIN writer Annette Stark, on assignment to find Cool J backstage in 1987, puzzled over her unfamiliar surroundings: "I sniff around for the old familiar rock'n'roll smells — beer, sweat, and weed — but all I get are competing whiffs of orange juice and aftershave." And then, just a couple years later, Sonic Youth's Kim Gordon wrote, "Radio was one of the things that turned me on to rap," in the intro to a Q&A in which she goes on to talk with LL about Andrew Dice Clay, sexiness, and the Stooges.

"America. Mom. Baseball. Apple pie. Crass commercialism. Imperialist foreign intervention. Steve Earle's first album Guitar Town is a lot like Reagan's America." So goes our original review, which frets over a suspected "compromise between country and rock" and wonders just how seriously to take Earle's rootsy charm. That skepticism would change in time, as Earle proved himself a serious and searching songwriter with chops. In 1995, SPIN found itself traipsing through Tennessee to learn more about Earle, who writer Mark Schone described as a "self-invented demographic of one: an ACLU gun nut, a biker-junkie-bookworm, a politically active high school dropout, a hopeless romantic with four ex-wives."

Dr. Dre's reputation preceded him ever since he started out as the producer of N.W.A — a group that SPIN took to a rowdy dinner at the Russian Tea Room in 1991. But it was with The Chronic that he truly shot off into the stratosphere. Dre's solo debut was full of "sinister odes, slow and sizzling, to life in the ghetto," as the magazine put it. Dre proved a more laid-back and appealing rapper than he'd been in N.W.A, and he had some considerable help from a certain new guest star named Snoop Doggy Dogg. And then there was the sound: a new form of gleaming, steaming G-funk that grew even more funky as it grew more minimalistic.

The alt-country revival never would've happened without Jeff Tweedy and Wilco, but evidently their major label thought they'd gone too far with this album, which SPIN called "the kind of Kid A-style breakthrough rock cults dream about." The band ended up releasing this "pastiche of experimental sonics and midlife rumination" via their website, and later through indie imprint Nonesuch. A 2009 cover story on Wilco reflected on how this pivotal album "nearly blew up the band"; the real-life drama resulted in the acclaimed music documentary I Am Trying to Break Your Heart.