A musician who appeared with Taylor Swift in one of her early music videos has shared insights into their unexpected friendship and his life since then.
Tyler Hilton, now 41, was cast as the romantic lead in Swift’s “Teardrops On My Guitar” video. This was one of her initial releases when she was an emerging country music artist.
By then, Hilton was already known for his role as Chris Keller in “One Tree Hill” and his portrayal of Elvis Presley in “Walk the Line” (2005).
While promoting his new children’s book, Hilton spoke to Us Weekly about meeting Swift, mentioning he was a fan before they met.
He had praised her songwriting in a country music magazine interview, not knowing Swift had been tracking his career online.
Her team reached out after that, saying Swift admired Hilton’s music and inviting him to one of her performances in Southern California.
During the show, the then 15-year-old Swift asked if he’d be in her upcoming music video, which resulted in his appearance in “Teardrops On My Guitar.”
Hilton’s appearance has changed significantly from that of the youthful image in the video.

The two maintained their friendship, with Hilton even spending several weeks living on the Swift family’s houseboat in Nashville after he moved to the city.
He described the Swift family as grounded, recalling nights spent listening to Taylor play unreleased songs, including early versions of “White Horse” from her second album.
Hilton has pursued his own path, releasing five studio albums and maintaining a career as an actor and composer.
His recent venture involves children’s literature, with his debut book, “Daddy: Live in Concert,” inspired by performing for his young daughter during the pandemic.

The book idea came from his daughter’s reactions when seeing him perform, despite her limited exposure to his touring life.
He aimed to capture the magic from a child’s view, offering a playful take on the traditional “my dad could beat up your dad” brag.
Reflecting on Swift’s ascent to worldwide fame, Hilton shared that he still struggles to grasp the magnitude of her success. He pointed to her early diary-style lyrics as evidence of her genuine songwriter persona. He believes this authenticity is a main factor in her enduring success.
Hilton stated that both songwriting and writing children’s books require similar creativity, though music often arises from a more somber place, whereas children’s storytelling allows for a return to a simpler, more cheerful mindset.