Tyler Hilton Is Down To Remake The “Teardrops” Video For Debut (TV)

Tyler Hilton might be best known for playing Chris Keller on One Tree Hill from 2004 to 2012, but longtime Swifties recognize him from another project. In 2007, Hilton took on the role of Drew in Taylor Swift’s “Teardrops on My Guitar” music video. Looking back, Hilton says he had “so much fun” working with Swift — and he’d be down to remake the music video when she re-releases her debut album.

In the song, Swift has an unrequited crush on Drew, who is “the reason for the teardrops on [her] guitar.” The music video features several scenes of Swift and Hilton at a high school — which makes sense, considering Swift was first introduced to Hilton’s work when she watched him on One Tree Hill, a high school drama. “I think she was a fan of the early seasons,” he says. “We connected because I heard her first single, ‘Tim McGraw,’ and I mentioned her in an interview. I said something like, ‘There’s this new girl out named Taylor Swift, and I think she’s really good.’”

After Swift saw Hilton’s interview, her manager invited him to one of her concerts. “They told me, ‘She’s going to be covering your version of “Missing You” from One Tree Hill. Do you want to get up and sing with her?’” Hilton says. “I agreed, and when I was on stage with her, she asked me to be in the video. She said something like, ‘I thought if I asked you on stage, you couldn’t say no.’ She was bold.”

At the time, Swift was 17, and Hilton was 23. “We became such good friends after that. It felt like this little sister, older brother vibe. Her family was so sweet, too,” he says. “I was so taken with her. I thought she was great.”

When he moved to Nashville years later, Hilton even lived on the Swift family’s houseboat. “Her bedroom had unicorns and princesses in it. She played me songs out of her diary,” he says. “None of that is an act — she really embraces who she is. It’s not always cool. It oftentimes exposes her to being made fun of because she can be a bit of a dork, but she leans into it. I love that about her.”

The two reconnected in 2018 when Hilton went to the Reputation Stadium Tour. “Her family was like, ‘Tyler, look at her. Isn’t she doing such a good job?’ They still act like they’re watching her at a talent show, and they’re filming her with their phones,” he says. “It’s like nobody has told them that she’s the biggest music star ever.”

Even now, Hilton still has a soft spot for Swift’s first record. “Debut was my album. I loved it so much, so I think Taylor’s Version will be great,” he says. “And maybe we’ll remake the old ‘Teardrops’ video for old time’s sake.”