This week on the Surely You Can’t Be Serious podcast, Jason and Dee dive headfirst into one of the defining albums of the 1990s—Alanis Morissette’s Jagged Little Pill. The guys trace Alanis’s remarkable rise from Canadian teen pop idol to alt-rock truth-teller, exploring how a young artist reinvented herself and ended up creating one of the most influential albums of the decade.

Jason and Dee unpack the creation of the record—from Alanis’s fateful collaboration with producer Glen Ballard, to the raw, confessional writing sessions that would reshape her public persona and give voice to a generation. They break down the production choices that gave the album its signature emotional punch and explain how Jagged Little Pill exploded into a cultural force that no one saw coming.

And of course, the guys tell the story behind every track: the heartbreaks, the therapy sessions, the studio magic, and the controversies that surrounded songs like “You Oughta Know,” “Ironic,” and “Head Over Feet.”

But this is just the beginning.
Over the next two weeks, Jason and Dee will compare Jagged Little Pill with Jewel’s Pieces of You and No Doubt’s Tragic Kingdom—two other iconic albums that shaped the 90s and launched careers. Which album has the strongest songwriting? The biggest cultural footprint? The deepest emotional resonance? And how will the guys ultimately rank these three 90s juggernauts?

Tune in as Jason and Dee rank them all—and maybe break a few hearts along the way.