From pop anthems to heartfelt ballads, music videos have become a canvas for artists to express their creativity and convey their stories. One artist known for her iconic visuals is Taylor Swift, and a noteworthy aspect of her music videos is the inclusion of numerous celebrities. In this article, we’ll explore all the celebs who have been in her music videos, highlighting the memorable appearances that have added star power to her storytelling.
Tyler Hilton in “Teardrops on My Guitar”
Tyler Hilton made an unforgettable cameo as Taylor Swift’s high school crush Drew in her 2007 music video, “Teardrops on My Guitar.” Hilton and Swift initially connected over their mutual admiration—he was a fan of her track “Tim McGraw,” and she enjoyed watching him on One Tree Hill. The two finally met when Swift invited him on stage to perform “Missing You.” Hilton recalled on a March 2025 episode of the When They Popped podcast, “She’s like, ‘I wanted to wait until you were on stage to ask you because I didn’t want you to say no, but will you be in my next music video?'”
The pair developed a close friendship, with Hilton even staying on the Swift family’s houseboat shortly after moving to Nashville. In 2018, they reconnected backstage during her Reputation tour. Hilton posted on Instagram: “You killed it bud, great seeing you and the fam, come a long way since Teardrops vid we did!!!”
While the narrative romance between Taylor Swift and Drew didn’t pan out in reality, Hilton did find love with Megan Park, whom he met on the set of 2007’s Charlie Bartlett. The couple married eight years later but announced their separation in January 2026. Presently, Hilton, also a musician, is touring with Kate Voegele and has featured in The Christmas Contract and A Christmas Wish alongside One Tree Hill alum Hilarie Burton.
