Rolling Stone is rolling out their annual Musicians on Musicians issue this week. Yesterday they revealed the first of four cover stories featuring Madonna and Maluma (not a piece I was eager to read because they’ve known each other for years and we’ve already heard them talk about each other), but today we get a much more exciting pairing: Olivia Rodrigo and Alanis Morissette. 


Let’s start with the cover. It has what I consider to be the old school, iconic Rolling Stone aesthetic, which is musicians standing in a white portrait studio, starring directly into the lens. It’s intimate and cool and feels so damn rockstar. Avril Lavigne got a similarly styled cover in 2003. Tina Turner gave us one of my favourite Rolling Stone covers ever in 1984 with a more Tina version. Alanis herself got the same aesthetic when she covered the mag solo a few months after releasing Jagged Little Pill in 1995. Back then the words “Angry White Female” were written across the cover, which feels so cringe all these years later. Now she’s joined by the young woman carrying the torch for angsty pop-rock female vocalists. 

Olivia and Alanis had never met before this conversation, which they had while cameras were rolling. What you get from the video that you don’t get from the print article is Olivia’s laughter — legitimate and otherwise. I think some of it is nervous laughter and fake giggles. But we can’t hold that against her. She’s an 18-year-old, fresh off the Disney lot sitting across from a music icon. Plus, she’s a fan! Olivia talks about being inspired by hearing Alanis in the car when she was young and mentions seeing Jagged Little Pill on Broadway before lockdown. Honestly, the nervous laughter adds to the endearing dynamic.


But there is an immediate warmth between them and I wonder how much of themselves they see in each other. Olivia notes how they both started as child actors and how they both had massively successful debut albums. Is Olivia seeing herself in 30 years? Or at least seeing where her trajectory could possibly take her? They bond over the art of songwriting and how they approach putting their personal experiences into their lyrics. You can feel there’s a respect Alanis has for Olivia. There’s a graciousness in being allowed to pick the brain of a young songwriter. If this was a conversation between Olivia and say… Madonna… we wouldn’t see this exchange of energy. We likely wouldn’t even see Madonna agree to the conversation. 

Alanis was a trailblazer in the music industry and unfortunately the music industry hasn’t let that trail she created become well-travelled. I think moments like this and artists like Olivia allow her to reflect on her own legacy, unlike Madonna who seems to want to hold onto the torch or gatekeep who gets the torch next. Alanis is happy to watch the torch from the sidelines and this conversation with Olivia gives me the impression she finds joy in watching talented young women pick it up and (hopefully) carry it further.