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Alanis Morissette's international debut detonated on alternative radio with "You Oughta Know" and never let up. At 21, she won the 1996 Grammy for Album of the Year, becoming the youngest recipient of that award at the time and selling over 33 million copies worldwide.
The melancholy glow of 1997 radio: Jakob Dylan—yes, that Dylan—singing about the death of ideas over the year's most inescapable groove. It topped every rock format at once, won two Grammys, and never even appeared on the Hot 100.
André 3000 and Big Boi met as teenagers at Lenox Square mall in Atlanta and launched one of hip-hop's most fearless acts. The South got something to say—literally—and hip-hop would never ignore it again.
Pretty, gentle, and secretly about a woman burning her house to the ground — Shawn Colvin's "Sunny Came Home" swept the 1998 Grammys, winning both Record of the Year and Song of the Year.