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1* AssPull: The music video for ''Crazy''. [[spoiler: 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. [[DullSurprise 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 RewatchBonus, 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.]]
2* AudienceAlienatingEra: 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-Music/MilliVanilli, and needless to say, they were emblematic of pop's troubles during the period judging by their content. To this day, Alanis [[OldShame disowns the albums entirely]], and radio stations have refrained from playing any music from them.
3* SugarWiki/AwesomeMusic:
4** All of ''Jagged Little Pill''. ''Especially'' "You Oughta Know", "Hand in My Pocket", "You Learn", and "Ironic".
5** "Uninvited". The song is already tense and beautiful enough, but then those drums kick in and it goes ''hard.''
6* CommonKnowledge: It's often said that nothing actually ironic happens in "Ironic", with some even claiming that [[IronicName 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.
7* EpilepticTrees: The identity of the ex-boyfriend that Alanis confronts in "You Oughta Know" has caused enough speculation that [[WMG/AlanisMorissette a WMG page]] was created.
8* FridgeBrilliance: The final chorus in "Ironic" drops the lines referring to assumptions that everything will always work out...[[{{Irony}} because life's funny way of helping her out was to teach her that life doesn't help you out]].
9* GermansLoveDavidHasselhoff: 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.
10* HilariousInHindsight: The "Eight Easy Steps" music video is a backwards-chronological showcase of past Alanis film clips and videos, with her [[DigitalHeadSwap face re-edited to look like she's singing the song]]. In other words, [[https://en.wikipedia.org/wiki/Deepfake deepfakes]] in 2004!
11* MemeticMutation:
12** "Isn't it ironic?"
13** "Would she go down on you in a theater?"
14* MisattributedSong: "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.
15* SequelDisplacement: ''Jagged Little Pill'' is more popular than her first two albums.
16* SignatureSong:
17** ''Jagged Little Pill'': "You Oughta Know", "Ironic", "Hand in My Pocket", "You Learn" and "Head Over Feet"
18** ''Supposed Former Infatuation Junkie'': "[[Film/CityOfAngels Uninvited]]" and "Thank U"
19** ''Under Rug Swept'': "Hands Clean"
20** ''So-Called Chaos'': "Everything", "Eight Easy Steps"
21** Overall: "You Oughta Know", "Ironic" and "Uninvited"
22* SurprisinglyImprovedSequel: Going from [[TeenIdol teen pop]] to ''Jagged Little Pill'' is a hell of a shift.
23* ToughActToFollow: Despite selling 2.4 million copies in the US, it's tough not to consider ''Supposed Former Infatuation Junkie'' a [[SophomoreSlump 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 DarkerAndEdgier and including elements like creepy Eastern string sections, heavier sampling, and louder guitars.

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