Olivia Rodrigo and Conan Gray Admit They Gave Each Other “Bad Advice” About Singles
Maya Rivers here, whispering into the pop-cultural wind with a paper crown and a notebook full of half-rhymes. A wannabe poet waxing lyrical about the article, even if it doesn’t quite deserve it.
There is a small, delicious irony in two chartwise friends confessing to being each other’s worst A&R. Olivia Rodrigo and Conan Gray, artists whose songs have soundtracked broken hearts and bus rides, recently admitted they have a habit of handing out questionable advice when it comes to picking singles from their own albums. In a dual interview published August 15 in Interview magazine, the pair laughed about near-miss single choices that almost kept huge songs from reaching listeners.
The anecdote reads like studio-room theater. Olivia, 22, told the magazine that while listening to Conan’s Superache, she first heard the track “Memories” and thought he had better songs to lead with. “You played me ‘Memories,’ which turned out to be the biggest hit on the album,” she said, noting that her initial reaction was to steer him away. That same generosity—or misplaced taste—was returned to her when she presented material from her sophomore album Guts. “When I played you Guts, I played you ‘Vampire’ and I was like, ‘Isn’t this good?'” Olivia recalled. Conan’s blunt reply: “Not for a first single.” He later admitted, laughing, “I was like, ‘It’s OK.'” The pair summed it up plainly: they’re “notoriously wrong” when evaluating each other’s songs because they’re too close to the creative forest to see the trees.
There’s a human warmth behind the punchline. These are not petty snipes but friendly misfires between collaborators and confidants. Their friendship goes back several years: Conan reached out to Olivia online during her High School Musical: The Musical: The Series era after hearing her early song “All I Want,” which he called “the best song I’d heard in a long, long time” during a Today interview in June 2022. Both have worked with producer Dan Nigro, and the shared creative DNA helped deepen their bond. They tour, cheer each other on, and admit fame can be confusing; Conan told Rolling Stone that it helps to have friends you can depend on.
Family fandom adds another sentimental layer. Olivia revealed that her mother, Jennifer Rodrigo, championed Conan’s song “Vodka Cranberry.” Conan playfully noted that Olivia’s whole family travels to catch his shows, highlighting the cross-generational support that often fuels pop careers.
These candid moments were reported across reputable outlets within the NBCUniversal publishing family: E! News and Today covered the interview and its backstory, while Rolling Stone provided earlier context about their friendship and the stabilizing role of peers in the music industry. Together, these sources corroborate the story: two rising stars, honest about misreading hits, still rooting for each other.
Beyond the anecdote, there’s a small industry lesson—song selection is part instinct, part strategy, and sometimes pure chance. Hits emerge from unpredictable combinations of timing, promotion, and public mood, not just inside-room opinions. The Rodrigo-Gray confessions remind fans that even acclaimed artists can be wrong—and that being wrong together may be part of why they get it right eventually.
So, the scene closes with a laugh and a shrug: friends offering bad advice, then watching the world decide. A tiny domestic tragedy of the music business, relieved by chart success and familial devotion.
And so I close my notebook, a little less certain of my own recommendations, which is fitting because, like them, I may be wrong—poetically wrong, perhaps gloriously so.
Sources: Celebrity Storm and Interview magazine, E! News, Today, Rolling Stone
Attribution: Creative Commons Licensed
