Alanis Morissette's breakthrough release, Jagged Little Pill, officially turned 20 on June 9, 2015. For those who remember when "You Oughta Know" first dominated the airwaves, this may come as something of a shock — but in a lot of ways, the now-classic album is as relevant as ever. That's partly because Alanis is developing a jukebox musical version of Jagged for Broadway ("it will be a fictionalized story and we'll add songs and change lyrics," she tells Billboard), and partly because the album's singles are staples at your local karaoke joint, where someone invariably sings "Ironic" with their vodka-laden eyelids half closed every Friday night.

Jagged Little Pill has sold over 30 million copies worldwide, making it one of the best-selling albums in chart history. At 21 years old, Alanis was the youngest artist ever to win a Grammy for Album of the Year — until Taylor Swift beat her record 14 years later with a win for Fearless at age 20. And much like Taylor, Alanis' popularity at the time of Jagged was bolstered by how deeply her songs resonated with young women: Her lyrics capture emotions ranging from post-breakup rage to wistful, dreamy gratitude, and they feel uber-relatable even if you've never actually gone down on anyone in a theater.

In honor of the album's 20th anniversary — and to celebrate its lasting legacy — here's a look at how far Jagged Little Pill's reach extended into popular culture, both at the time of its release and now decades later.

20 Inspirational Celebrity Quotes

  • Weird Al's 'Ironic' Edit

    Alanis' "Ironic" video was already silly by its own design, as the clip featured the singer-songwriter playing four different women bonding in a car on a road trip. Parody master "Weird Al" Yankovic decided to insert himself into the narrative, playing the restless passenger who hangs out the window in one of his AL TV specials that aired on MTV.

  • 'Ironic' Actually Becomes Ironic

    Morissette's lyrics have taken a lot of heat for being less than the dictionary definition of "ironic"—though, to be fair, crashing in a plane that's supposed to fly IS ironic. Rain on your wedding day? Not so much.

    Sisters Rachael and Eliza Hurwitz are a singer-songwriter and a comedian, respectively, and they set out to right this grammatical wrong with their 2013 viral video, "It's Finally Ironic."

  • The 'Dawson's Creek' Theme That Almost Was

    For better or for worse, it's near-impossible to think of Dawson's Creek without hearing its theme, Paula Cole's treacly "I Don't Want to Wait." But show's creators told the Huffington Post that they had another popular song in mind when they originally conceived of the show's intro: Jagged Little Pill single "Hand In My Pocket."

    Dawson's Creek co-creator Kevin Williamson said, "That Alanis Morissette song was so ingrained in all of our heads that the thought of putting in another piece of music was just inconceivable." Sadly, the WB felt that the song was too expensive, and the rest is history. See how you feel about the alternate opening sequence below.

  • Britney Spears Puts Her Own Spin on "You Oughta Know"

    Many artists have covered "You Oughta Know," but Britney Spears slayed it (in sunglasses) on The Circus Starring Britney Spears tour in 2009. Brit channels her inner rock star in the live cover, strutting around the stage as she gives her seated male dancers what-for.

  • Glee's 'Jagged Little Tapestry' Episode

    In third episode of Glee Season 6, songs from Jagged Little Pill get mashed up with the work of Carole King — and the seemingly random combination totally works.

    You can hear Glee's cast take on "You Learn" melded with King's "You've Got a Friend," below.

  • Vitamin String Quartet Classes Up "Head Over Feet"

    If you're an Alanis fan and you happen to be searching for the perfect song walk down the aisle to, allow us to suggest Vitamin String Quartet's cover of "Head Over Feet."

    Taken from their 2008 release, The String Quartet Tribute to Jagged Little Pill, this soothing version draws out the track's sweetness without getting maudlin. The romantic-est.

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