Olivia Rodrigo and Conan Gray, two of Gen Z's most prominent voices in music, have revealed a surprising aspect of their close friendship: they often give each other "notoriously bad advice" when it comes to their music. The pair, known for their unwavering support for one another, admitted that their closeness sometimes hinders their ability to provide objective feedback, leading to some near misses with hit singles.
In a recent conversation for Interview magazine, Rodrigo, 22, and Gray, 26, discussed how their misjudgments almost prevented the release of some of their most successful songs. Rodrigo confessed, "We notoriously give each other bad advice sometimes about samples". She recalled a time when Gray played her "Memories" from his 2022 album, Superache. Despite the song becoming the album's biggest hit, Rodrigo admitted her initial reaction was, "I just think you have better songs".
Gray, whose fourth studio album Wishbone was released on August 15, 2025, had a similar experience with Rodrigo's music. When Rodrigo was preparing to release her 2023 album Guts, she sought Gray's opinion on "Vampire," which she considered a strong contender for a single. However, Gray advised against it, saying, "Not for a first single". "Vampire" ultimately became a chart-topping hit, proving their contrasting tastes. Rodrigo reflected, "We're notoriously wrong about each other's songs. We're just too close to it and can't see the forest of the trees".
Despite their occasional missteps in musical guidance, their bond remains strong. Rodrigo expressed her admiration for Gray's latest album, Wishbone, even admitting she was "a little worried" when he was creating it, feeling he had become too "obsessed". She told Gray, "You seemed so obsessed with this album and you weren't doing anything else. You were just eating, breathing, and sleeping this album. And I'm like, 'Oh, I just don't know if that's really healthy'". However, upon hearing the demos, she was blown away, stating, "Damn, these are so good... I just remember being so proud of you," and encouraging him to promote it relentlessly.
Their friendship began several years ago, fostered by their shared love for music and their connection to producer Dan Nigro. They also bonded over their mutual admiration for Taylor Swift. Since then, they have supported each other's careers, attended events like the Met Gala together, and showcased their close bond on social media.
Rodrigo's Guts world tour recently concluded after 102 shows across five continents. The tour grossed over $196.7 million and drew approximately 1.5 million fans. Rodrigo also seems to be hinting at new music, with updates to her website and a teaser at the final performance of the GUTS tour. Gray is set to embark on the Wishbone Pajama Show in September and October 2025 to support his new album.
