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Produced by Walaa Elsiddig and Jenny Martin.
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Photographed by Yana Yatsuk for Rolling Stone.
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I went down many rabbit holes knowing I was going to meet you.” “Well, you’re doing the same,” replies Morissette, 47, who’s been touring to celebrate the 25th anniversary of Jagged Little Pill. “I love how you’re so honest and talk about stuff that normally isn’t talked about in songwriting,” says Rodrigo, whose album, Sour, is one of the year’s most streamed by a healthy margin. They even both have hit singles whose music videos feature them navigating mixed feelings in a moving vehicle (“Drivers License” and “Ironic”). Both of their careers exploded beyond their wildest expectations when they switched their focus to music, releasing blockbuster albums that used intensely personal details to strike universal chords of heartbreak.
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Both began as child actors (Rodrigo on Disney+’s High School Musical: The Musical: The Series Morissette on the Canadian sketch show You Can’t Do That on Television). Rodrigo and Morissette might be nearly 30 years apart, but they’ve gone down similar paths. “I feel like if I do one, I’m going to want to do so many more.” Her idol offers a word of advice: “Don’t get a tattoo unless you’ve been married 47 years.” “No! I just turned 18!” Rodrigo says with a laugh. Soon, they get more personal, with Morissette asking Rodrigo if she has any tattoos. Prior to the interview, they casually discuss topics that range from Halloween (Rodrigo’s favorite holiday) to Germany (where Morissette briefly lived as a child). Morissette rocks firecracker-red heels, while Rodrigo is disco-ready in platform leather boots that she swears are comfortable. The two songwriters - who are big fans of each other’s music, but have never met before today - sit facing one another in dark blazers in a San Francisco warehouse overlooking the Pacific. If anyone can understand the roller coaster that Olivia Rodrigo has been on this year, it’s Alanis Morissette. We’ll be rolling out all 10 stories this week and next, so check back often. Each story in this year’s series will appear in our November 2021 print issue, hitting stands on November 2nd - with four special covers, including this one. Welcome to Rolling Stone’s 2021 Musicians on Musicians package, the annual franchise where two great artists come together for a free, open conversation about life and music.