Olivia Rodrigo And Conan Gray Fearlessly Perform Taylor Swift's Re-Recorded Songs

With the re-recording of her 2008 album Fearless set to drop on Friday (April 9), Taylor Swift has tapped her "kids" Olivia Rodrigo and Conan Gray to create their own wholesome, DIY videos inspired by two of her biggest hits from the Fearless era: "You Belong With Me" and "White Horse."


In a tweet on Thursday (April 8), Swift shared that she had sent Gray and Rodrigo an advance copy of the re-recording of her legendary single “You Belong With Me" and her reaction to their corresponding video, which features the two singing the song's chorus into hairbrushes, was correctly wholesome. “You ok? NO cause I sent my two kids @Olivia_Rodrigo and @conangray my new version of You Belong With Me And so they ARE SO Pretty IT PHYSICALLY HURTS ME,” she tweeted.


In the TikTok clip, Rodrigo and Gray pay homage to Swift’s 2008 “You Belong With Me” music video, wherein Swift and her crush, who happens to be her next-door neighbor, correspond with one another by writing signs and holding them up to their windows. “Conan, you ok?” Rodrigo’s sign reads. “No bitch, I’m listening to the Fearless re-records,” Gray’s sign answers before the two start dancing and singing on a bed just like Swift in the music video.


But the duo didn't stop there. They also filmed a hilarious take on the poignant country ballad "White Horse" in which both artists don cowboy hats and reenact the song's lyrics.  Gray literally sweeps Rodrigo off her feet and leads her up the stairwell before ending on a gloriously timed turn and tip of their cowboy hats. Rodrigo wrote on Instagram, “We got a sneak peak of ‘White Horse (Taylor’s Version)’ and we just had to prepare this vid. One of my main go to songs of all time. In response, Swift shared the video on her Instagram Story and appropriately captioned it: “sobs in yeehaw.”


Last month, Rodrigo told Radio.Com that she had gotten a handwritten letter from Swift that left her reeling. “My tears are on it, my snot from sobbing my eyes out is on it. I love her,” she said.


She also revealed that Swift imparted some key career suggestions in the letter as well: “She’s like, ‘I think we make our own luck and I think any time you’re kind to people and do what’s right, it routinely comes back to you in the perfect way.’ I just enjoy her and that’s what I’ve literally been thinking about since I opened that thing last night. It’s the only thing in my brain.”