That year, The Smashing Pumpkins took home a small army of Moonmen for “Tonight, Tonight,” the spectacular, animated counterpart for the symphonic single off their double album Mellon Collie and the Infinite Sadness. The video swept nearly every category it was nominated for, including Video of the Year, and the performance they gave at the top of the ceremony felt poignant: The band had endured the death of one member and the departure of another in the weeks leading up to the VMAs, but they took the stage at Radio City Music Hall anyway, with the might of an orchestra and the projected constellations of the cosmos unfurling behind them.
But The Smashing Pumpkins had competition, to be sure, and every time a presenter read the words “And the winner is …” off the teleprompter, it felt like there was a decent chance that Alanis would sweep in and nab the Moonman instead. As grand an artistic achievement as “Tonight, Tonight” was, her “Ironic” video was just as ambitious. In many ways — style, tone, execution, scope — it was the polar opposite of “Tonight, Tonight.” Where the Pumpkins’ video was a magnificent sprawl reliant on magical thinking, “Ironic” was dumbfounding for its rad simplicity and realness. Everyone could relate to its scenes, which involved driving around with friends on a blustery morning and screaming along with your favorite song on the radio. The twist: Alanis spent the video driving around with four versions of herself, rolling through the verses of “Ironic” with a steadily emptying tank of gas and the defrost on the fritz.
The camera lingered on Alanis’s beaming face as she belted out the single’s chorus, melting the snow thanks to the sheer force of euphoria emanating from her banging head, her whipping, matted locks, her laughing eyes, and rambunctious, death-defying hijinks when she nearly vaulted herself out of the car’s window. The video was nominated for six awards that night, and though it lost the honors of Video of the Year, Viewer’s Choice, and Best Direction to “Tonight, Tonight,” it scored Alanis her first Moonmen for Best Female Video, Best New Artist in a Video, and Best Editing in a Video. Billy Corgan’s two-dimensional top hat was a marvel, but Alanis cloned herself — a masterstroke in a moment when the world was crying out for more Alanis.
It was as much a cinematic achievement as it was another feather in the cap of an astounding debut year. “Ironic” was the third single on a record full of memorable anthems and staggering, unflinching rock that remain her most adored songs to date. Alanis walked into the 1996 VMAs a decorated winner already: Jagged Little Pill, her first record to break outside of her native Canada, was released on June 13, 1995, a full year and change before “Ironic” would give “Tonight, Tonight” a run for its money at Radio City Music Hall. She performed at the VMAs that year, scorching the stage with “You Oughta Know”; a few months after that, at the 1996 Grammys, Jagged Little Pill would net five of the statuettes it was up for, including Album of the Year, which made Alanis, at 21 years old, the youngest artist to earn the distinction. (She’d hold on to that record until 2010, when Taylor Swift won the title for Fearless at the age of 19.)
Though “Ironic” was the third single from Jagged Little Pill, its music video is the most notable visual achievement attached to the album, justifying the better-late-than-never fanfare it got in 1996. The fact that the video was the only female contribution to the categories of Video of the Year and Viewer’s Choice at the 1996 VMAs only bolstered her badassery, and spoke to the staying power of the album itself — and the artist who made it.
In the decades following its release, Jagged Little Pill and Alanis have been name-checked by pop stars like Katy Perry as pivotal inspirations. Alanis is now mounting a musical based on the album. And when she recently hit The Late Late Show with James Corden to update the lyrics of “Ironic” for the digital age, she made sure to rock the braids and beanie she sported for the video that cemented its cult status. Even though "Tonight, Tonight" was the big winner two decades back, "Ironic" is the one that speaks to us today — and there's nothing remotely unfortunate, or even ironic, about that.
Tune in to the 2016 VMAs, live from New York on Sunday, August 28, at 9 p.m. ET/PT.