Unapologetically honest songs about figuring it all out.
Jagged Little Pill
Alanis Morissette
31
Alanis Morissette’s blockbuster third LP (following two teen-pop records that went Top 40 in her native Canada) was poetic and straightforward, cynical and idealistic, sarcastic and wide-eyed. It is also fearlessly confrontational, with sharp-edged criticisms of Catholicism, technology, and boyish men that few artists since have had the guts to echo. So when the 21-year-old former Nickelodeon star released it in 1995 after being dropped by her label, its unapologetic worldview hit different, offering a level of frankness and vulnerability that cut a path for generations of future singer-songwriters, Taylor Swift and Olivia Rodrigo among them.
“I remember saying to myself that I wouldn’t stop writing until I loved it with all of my heart.”
Alanis Morissette
Beneath the record’s radio-friendly hooks and shiny harmonies were observations on the messiness and banality of life. Human weakness is a theme—she’s distracted on “All I Really Want,” disoriented by happiness on “Head Over Feet.” Yet even if the album’s core spirit is disillusionment, its legacy is hopefulness—the idea that bleeding, screaming, and learning is also, ultimately, living. Perhaps that’s why, for all her angst and anger, Morissette is relatively kind to herself. In the easygoing “Hand in My Pocket,” now a time capsule of cigarettes and taxi cabs, she forgives herself for not having it all figured out.