The Black Fly in Your Chardonnay: Jagged Little Pill at 25

The cover of Jagged Little Pill by Alanis Morissette

I vividly remember the day I listened to Alanis Morissette’s Jagged Little Pill for the first time. I was in 7th grade and a classmate slid it across the table to me in the last period. It was in a piecemeal jewel casejust the liner notes and the CD. The inset and backsplash of the case was actually from Boyz II Men’s II album. It didn’t matter. Back then, getting a mixtape or burned CD from someone was special. Borrowing someone else’s album was god tier. It was both personal collateral and a supreme act of trust. 

By this point, I had some baseline knowledge of Alanis Morissette. I’d seen the gritty, jewel-tone soaked video for “You Oughta Know” on MTV all summer, and read reviews in local weekly papers and Rolling Stone alike. Somewhere Madonna’s name was dropped in conjunction (since her label Maverick was involved) and since she was the pinnacle of art and music for me (at the time) that seemed like the biggest blessing this album could get. 

Swallow It Down: Anger as Art

The Angry Female Singer is the archetype of the ‘90s, thanks to bigwigs and radio stations. But there were differing levels of emotion, from the likes of Tori Amos, PJ Harvey, Bjork, Hole, Liz Phair. The list goes on and on, and at some point would turn into Lilith Fair thanks to Sarah McLachlan. 

But no one crystalized anger like Alanis. Unlike some of the other aforementioned artists (who I hold in the highest regard), Alanis made anger tangible and utterly understandable with biting words and clear-as-day metaphors and simile. Many of the lyrics came from her personal journals and she was hesitant to put them in. Thankfully, producer Glen Ballard encouraged her to speak her truth, and for that, millions of people felt seen, for whatever reason. Whether they had their heart broken (“You Oughta Know”) or were seen only as a sex object (“Right Through You”) and were seething, they were seen. Or if they struggled with religious guilt (“Forgiven”), drug use (“Mary Jane”) or well-meaning helicopter parents (“Perfect”), they were seen. Or if they finally found an almost-too-good-to-be-true relationship (“Head Over Feet”), they were indeed seen. 

For all the fuss that was made about her anger, there’s an organic vulnerability to this collection of songs. Alanis’ heart is literally on her long satin sleeve, and it feels like she gave us the whole garment to wrap up in when the world was too much. Nowhere is this more evident than the hidden track, “Your House,” where she sneaks into a lover’s house only to discover she’s been cheated on and her joyful dancing turns to tears. Her acapella vocal is raw, a synergistic suburban banshee. I remember when the album ended and recycled to the first track I had to stop it and just breathe–and it felt like the first breath of a whole new life, a whole new perspective I hadn’t considered or couldn’t outwardly communicate. 

And Yeah, I Really Do Think: Wit and Wisdom

Jagged Little Pill has many moods and colors, and one of the brightest (ironically) is the black humor. It starts with the list of contrasts that is “Hand in my Pocket:”

“I’m free but I’m focused, I’m green but I’m wise

I’m hard but I’m friendly, baby

I’m sad but I’m laughing, I’m brave but I’m chicken shit

I’m sick but I’m pretty baby

And what it all boils down to

Is that no one’s really got it figured out just yet”

And then there’s the iconic, much argued “Ironic” which may or may not be filled with ironies. All unfortunate scenarios aside, the song actually backs up the theme of “You Learn:” 

“Well, life has a funny way

Of sneaking up on you

When you think everything’s okay

And everything’s going right

And life has a funny way

Of helping you out

When you think everything’s gone wrong

And everything blows up in your face”

I remember DJs tried to unearth her previous pop albums, which ranged from pure pop to jack swing. I got my hands on them years later and, yes, they are dated as hell, but Alanis and her trademark introspectiveness and wit are heavily cloaked amid early 1990s pop stylings, black blazers, permed hair, and music video dance routines. In short, she was always smart, she just wasn’t allowed to show it yet (see also Tori Amos’ Y Kant Tori Read album for a similar transformation). Thanks to her courage to open up and explore with Glen Ballard, she was able to not only leave that framework but to completely burn it to the ground and the gorgeous embers became Jagged Little Pill

Songs like “All I Really Want,” “Not the Doctor,” and “Wake Up” round out the album’s wry and wise look at life, despite the fact that Alanis wasn’t even in her 20s yet. As the quiet yet well-read girl sitting in the back of the class, I appreciated her sarcasm and angst, in equal amounts. 

Frustrated by Your Apathy: An Afterword of Sorts

With the release of Supposed Former Infatuation Junkie, many dedicated and casual fans alike seemed mad that Alanis wasn’t angry anymore. Catharsis gave way to even deeper introspection, and in many ways, I believe Supposed Former Infatuation Junkie is just as important as Jagged Little Pill but in exquisitely different ways, and a real continuation of the journey she started here. Yet, Jagged Little Pill is its own microcosm of emotion, frozen in time like an old faded polaroid stuck to a mirror. I remember exactly who I was when I first listened to this album, just an awkward girl trying to work through her emotions on her own, and how she was able to slowly grow into someone stronger over time. 

The other day, I went for a long drive and Jagged Little Pill was the CD I slipped into the player. I pumped up the volume, spitting the lyrics out into the chilly compartment. In the “Ironic” music video, there are four different versions of Alanis that fill up the seats of the car. And maybe that’s the enduring appeal of this album, after all this time. She invites us to take not one seat but several. Each seat allows them to process their emotions as they see fitanger, vulnerability, and witso once the next leg of the journey begins, we are whole once more. When I pulled back in my driveway, I felt like I could breathe for the first time in months. Some things never change. And isn’t it ironic?

“You live you learn, you love you learn

You cry you learn, you lose you learn

You bleed you learn, you scream you learn

You grieve you learn, you choke you learn

You laugh you learn, you choose you learn

You pray you learn, you ask you learn

You live you learn”

Written by Rachel Stewart

Rachel Stewart is a staff writer at 25YL. She has written fandom commentary and critique for sites like The Sartorial Geek,, Nerdy Minds Magazine, and ESO Network, among others. Her work has also appeared in print in the kOZMIC Press anthology “Children of Time: The Companions of Doctor Who" and the ATB Publishing anthology "OUTSIDE IN TRUSTS NO ONE."

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