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  • Ass Pull: The music video for Crazy. The only hint that the unnamed blonde is Alanis's girlfriend is the photo by Alanis's bedside near the start of the video, which is small, easily missed, and easily mistaken for a photo of two friends. When Alanis confronts the couple at the club, the girlfriend doesn't remotely react how you'd expect a cheater to. She barely reacts at all, in fact. Even at the end of the video, she doesn't seem a bit worried about how her violent girlfriend will react. On a Rewatch Bonus, you may realize why the guy looks stunned, not guilty, while the bouncer hauls Alanis out of the club because the blonde just presumably told him the truth, but on the first watch, it looks like the blonde just dumped him because she learned he was a cheater.
  • Audience-Alienating Era: Her first two albums Alanis and Now Is the Time came out at a time when pop music had become ear poison for audiences post-Milli Vanilli, and needless to say, they were emblematic of pop's troubles during the period judging by their content. To this day, Alanis disowns the albums entirely, and radio stations have refrained from playing any music from them.
  • Awesome Music:
    • All of Jagged Little Pill. Especially "You Oughta Know", "Hand in My Pocket", "You Learn", and "Ironic".
    • "Uninvited". The song is already tense and beautiful enough, but then those drums kick in and it goes hard.
  • Common Knowledge: It's often said that nothing actually ironic happens in "Ironic", with some even claiming that the song's name is therefore the real irony. Actually, while some of the things listed are just sad, many of the situations described, like the flight passenger who thinks "Well, isn't this nice?" as his plane comes crashing down, are genuine examples of irony.
  • Epileptic Trees: The identity of the ex-boyfriend that Alanis confronts in "You Oughta Know" has caused enough speculation that a WMG page was created.
  • Fridge Brilliance: The final chorus in "Ironic" drops the lines referring to assumptions that everything will always work out...because life's funny way of helping her out was to teach her that life doesn't help you out.
  • Germans Love David Hasselhoff: When Alanis released Jagged Little Pill in 1995, she became a megastar across the border but had a tough time getting airplay in her home country of Canada because she already had a past there as a Debbie Gibson-style teen-pop diva in the early '90s. In fact, Ottawa media outlets were flooded with complaints from disgusted citizens when she was given a key to the city.
  • Hilarious in Hindsight: The "Eight Easy Steps" music video is a backwards-chronological showcase of past Alanis film clips and videos, with her face re-edited to look like she's singing the song. In other words, deepfakes in 2004!
  • Memetic Mutation:
    • "Isn't it ironic?"
    • "Would she go down on you in a theater?"
  • Misattributed Song: "One Of Us" by Joan Osbourne is sometimes credited to her, due to having a very typical 90s alt. rock sound and being performed by a woman. Same goes for "Bitch" by Meredith Brooks.
  • Sequel Displacement: Jagged Little Pill is more popular than her first two albums.
  • Signature Song:
    • Jagged Little Pill: "You Oughta Know", "Ironic", "Hand in My Pocket", "You Learn" and "Head Over Feet"
    • Supposed Former Infatuation Junkie: "Uninvited" and "Thank U"
    • Under Rug Swept: "Hands Clean"
    • So-Called Chaos: "Everything", "Eight Easy Steps"
    • Overall: "You Oughta Know", "Ironic" and "Uninvited"
  • Surprisingly Improved Sequel: Going from teen pop to Jagged Little Pill is a hell of a shift.
  • Tough Act to Follow: Despite selling 2.4 million copies in the US, it's tough not to consider Supposed Former Infatuation Junkie a disappointment when compared with Jagged Little Pill's 16 million copies. It didn't help that Junkie was far more experimental than Pill and had a sharp divergence in Alanis's sound, becoming more Darker and Edgier and including elements like creepy Eastern string sections, heavier sampling, and louder guitars.
  • Vindicated by History: There are many notable parodies of Alanis's singing style during her peak in the 1990s and early 2000s. In 2015 and 2016, she returned to the public eye to promote the 20th anniversary of Jagged Little Pill. Now in her early forties, Alanis's songs from that time period still seem as fresh as they did in the 1990s.

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