Alanis Morissette

Before 1995, Alanis Morissette was a Canadian dance-pop fixture, two albums released only in her home country: Alanis (1991) and Now Is the Time (1992). Then June 1995 arrived with Jagged Little Pill, and she stopped being a teen novelty and became a worldwide phenomenon—33 million copies sold, her name on every tongue. "You Oughta Know" announced the reinvention — a scorched-earth open letter to an ex that nobody who heard it ever forgot. The 1996 Grammys crowned her with four awards, including Album of the Year; she was the youngest winner of that category at the time. The world felt newly permissioned to be angry out loud.

Jagged's follow-up, Supposed Former Infatuation Junkie (November 1998), doubled down on the oversharing—stream-of-consciousness lyrics, personal obsessions, wordy and unapologetic. It moved 469,000 copies its first week, a sales record for a female artist at that moment in time. "Thank U" became its thesis: introspective, unflinching. But some listeners felt exhausted by the intimacy; the album was a hit but it felt different—a fracture in the consensus. She played God in Kevin Smith's Dogma (1999), a perfect symbolic role for a woman the culture had put on a pedestal only to pick apart. Seven Grammys across her career. An entire 90s pastime became debating whether "Ironic" was actually ironic (it wasn't, and that was the point—the song was doing what she always did, saying exactly what it meant).

So-Called Chaos arrived in 2004 and did not top the chart. It was the first album where the machinery stopped working, the chart position slipping, and the imperial phase quietly ended. But the 90s Alanis had already left her imprint: she gave the decade permission to feel, to complain, to be a mess and call it art.