Before Taylor Swift made heartfelt hits about her love affairs, there was Alanis Morisette and “You Oughta Know.” As an effort to entertain, educate,and possibly diss frenemy Katy Perry, the 1989 artist brought Alanis over to her LA show to sing what could possibly be this generation’s greatest breakup song.
Nearing her 20thanniversary since Jagged Little Pill, her successful debut album, Alanis joins Taylor in a rendition of her well-known ’90s hit. Taylor seems aware of the obvious audience-and-performer age gap, and explains her guest’s appearance.
“She defined the music of her decade,” she begins. “She inspired a generation of confessional female singer-songwriters who all of a sudden felt like you could actually say these raw feelings that you had. You could actually sing about your real life, you could put detail to it, you could get really, really made if you wanted to. And I think it’s fair to say that so many of the female singer-songwriters of my generation, including myself, would not write the way that we do without her and her music. And she has written some of the most brilliant music—in particular probably inarguably the greatest breakup song of all-time.”