Tyler Hilton’s Viral Throwback to His Taylor Swift Moment

This week, Tyler Hilton joined a popular social media trend and reminded fans that he once played a starring role in one of Taylor Swift’s earliest music videos.

Hilton, now 42, shared an Instagram video set to Fleetwood Mac’s “Silver Springs,” using a popular caption format that encourages people to take chances in life. Across the clip, which shows scenes of him with Swift in her “Teardrops on My Guitar” video, he wrote, “In your 20s Taylor Swift will ask you to play a part in one of her music videos.... it’s very important you play that part.”

He added a playful caption beneath the post: “An OG Swiftie over here in case anyone was wondering #teardropsonmyguitar #taylorswift #swiftie #musicvideo.”

Before many fans knew him as Chris Keller on One Tree Hill, Hilton began his career as a musician. He landed his breakout acting role on the teen drama in 2004, but music remained an important part of his life. That love of songwriting is what first connected him to teenage Taylor Swift years later.

Last year, Hilton remembered the moment he first heard Swift’s debut single. He shared with PEOPLE, “I’m not embarrassed to say I was blown away by that song ‘Tim McGraw,’ ” Hilton said of the 2006 single. “ ‘Cause I’ve never heard as a writer something so simple and so earnest as: ‘When you hear Tim McGraw, I hope you think of me.’ ”

After publicly praising Swift in a media interview, Hilton had no idea his words would reach her directly. “I didn’t know this, but she was a huge fan of mine,” he said. Soon after, Swift’s management contacted him with an unexpected invitation. They asked if he would come sing one of his songs with her at a concert in California.

“I was like, ‘Whoa, if she’s doing one of my songs, I’ve got to go. That’s really adorable,’ ” Hilton recalled. “I went to this bar to check her out and it was packed — like 200 people in this little bar.”

While they were onstage that night, Swift surprised him with another offer. She asked if he would appear in her upcoming music video. Hilton said yes and traveled to Nashville to play Drew, the love interest in the now-iconic “Teardrops on My Guitar” video.

The connection did not end when the video wrapped. Hilton stayed in touch with Swift and her family, and when he first moved to Nashville, he even lived on their houseboat for a time.

“Her dad really helped me get settled out there,” he told PEOPLE. “And I just ended up getting into the whole Swift family world, and they were so cool.”

Now, nearly two decades later, one short Instagram video has brought that full-circle moment back into the spotlight. With one Fleetwood Mac song and a few old clips, Hilton reminded fans that sometimes taking a chance really does turn into a story worth telling.