Raph_PH · CC BY 4.0

Alanis Morissette released two dance-pop albums as a teenager in Canada before reinventing herself in Los Angeles with 1995's Jagged Little Pill, a confessional alternative-rock album that became one of the best-selling records of all time and made her, at 21, the youngest person to win the Grammy for Album of the Year. She kept creative control of her sound through later records, producing 2002's Under Rug Swept herself and winning the Jack Richardson Producer of the Year Award — a rarer credit for a woman in the genre at the time.