Track 15 from Flavors of Entanglement (2008)

Track 16 from Havoc and Bright Lights (2012)

Track 17 from Such Pretty Forks in the Road (2020)

Track 18 from The Storm Before the Calm (2022)

As a teenager, Alanis Morissette released two successful albums in Canada in the early '90s, one of which went platinum in Canada and one that went gold. But once Jagged Little Pill became a massive international hit, those early albums were treated as kind of her dirty little secret, her 'teen pop' albums. Her label, Maverick, actually went to the extraordinary lengths of actually persuading her former label, MCA, to take all copies of those two albums out of circulation. Morissette has said she's not embarrassed by those albums, but they've remained out of print, and she was talked out of including any songs from them on a best-of compilation. So I couldn't include any pre-Jagged Little Pill music in this playlist, much as I'd like to, just to offer a more complete picture of her career. 

I was too young to be conscious of Thriller while it was happening, but Jagged Little Pill is probably one of the biggest albums I've ever experienced firsthand as a pop culture phenomenon, up there with Get Rich Or Die Trying or Teenage Dream, if not bigger. That might be forgotten a bit because Alanis never maintained that kind of pop culture profile with her subsequent albums, and that female alternative-pop crossover artist niche was only a really big multiplatinum market in the '90s. I didn't care for most of Alanis's singles at the time, but there were some great songs off that record. I was in middle school at the time, and completely besotted with a girl who loved Alanis, so the album brings back a lot of memories. 

Jagged Little Pill was a fairly eccentric and individual blockbuster, and from there Alanis could've either acclimated to pop stardom to become a consistent hitmaker, or doubled down on her weirdest instincts and became a big name cult artist. Instead, she did neither, which in its own way is a pretty individual path to take. "Thank U" felt like a bold lead single, but Supposed Former Infatuation Junkie otherwise sounds a lot like Jagged, mostly in a good way. "Knees Of My Bees" aside, the titles of her albums were often the strangest things about them. Last year, Alanis finally really departed from conventional pop/rock with an ambient "meditation album," The Storm Before the Calm. 

Alanis seems to like guys that make her laugh, because in addition to her relationship with Dave Coulier that famously inspired Jagged Little Pill, Flavors of Entanglement reflects on her broken engagement to Ryan Reynolds. And many years after Alanis played God in Kevin Smith's Dogma and recorded a song for the soundtrack, it came to light that Supposed Former Infatuation Junkie's opening track "Front Row" is about Smith and Morrissette having some kind of brief relationship or almost-relationship, which even now is just kind of hilarious to think about.