The 8 Most 2000s Things to Happen toOne Tree Hill's Tyler Hilton — Including Living on Taylor Swift's Houseboat

Mar. 15, 2025

Hilarie Burton, Sophia Bush and Tyler Hilton on ‘TRL’ in 2006.Photo:Scott Gries/Getty

Scott Gries/Getty

Tyler Hiltonlived it up in the 2000s.

The multi-hyphenate, who starred onOne Tree Hillas Chris Keller starting in 2004, started his career as a musician though kicked off an acting career in the early 2000s and found himself with multiple roles that included starring as Elvis in 2005’sWalk the Line.

In a journey that included appearing as Drew inTaylor Swift’s “Teardrops on My Guitar” (and living on her parents' house boat!) to opening up forHilary Duff, Hilton checked off many boxes on the list of iconic and oh-so-very 2000s moments.

01of 08Having to Change His Number After Paris Hilton’s Phone HackTyler Hilton, Paris Hilton.Carley Margolis/FilmMagic; Gregg DeGuire/WireImageBack in 2005, whenParis Hilton’scell phone was hacked— leaking personal photos of the entrepreneur as well as phone numbers of her famous pals, Tyler was among one of the many people impacted.“When Paris Hilton’s phone got hacked and everyone’s number came out, I had to get rid of my phone because it wouldn’t stop ringing for like two weeks,” he told PEOPLE. “Very2000s.”

01of 08

Having to Change His Number After Paris Hilton’s Phone Hack

Tyler Hilton, Paris Hilton.Carley Margolis/FilmMagic; Gregg DeGuire/WireImage

Carley Margolis/FilmMagic; Gregg DeGuire/WireImage

Back in 2005, whenParis Hilton’scell phone was hacked— leaking personal photos of the entrepreneur as well as phone numbers of her famous pals, Tyler was among one of the many people impacted.

“When Paris Hilton’s phone got hacked and everyone’s number came out, I had to get rid of my phone because it wouldn’t stop ringing for like two weeks,” he told PEOPLE. “Very2000s.”

02of 08

Appearing on ‘TRL’ — Multiple Times!

Tyler Hilton on ‘TRL’ in 2006.Scott Gries/Getty

03of 08Opening for Hilary DuffHilary Duff and Tyler Hilton both performing at the Greek Theatre in L.A. on July 12, 2005.John Shearer/WireImage (2)Though many knew Hilton from his role onOne Tree Hill,he was a musician long before he considered himself an actor. In 2005, he opened forHilary Duff’s “Most Wanted” tour (so yes, he got a front-row seat to “Come Clean” every night).

03of 08

Opening for Hilary Duff

Hilary Duff and Tyler Hilton both performing at the Greek Theatre in L.A. on July 12, 2005.John Shearer/WireImage (2)

John Shearer/WireImage (2)

Though many knew Hilton from his role onOne Tree Hill,he was a musician long before he considered himself an actor. In 2005, he opened forHilary Duff’s “Most Wanted” tour (so yes, he got a front-row seat to “Come Clean” every night).

04of 08He Lived on Taylor Swift’s Family HouseboatTaylor Swift, Tyler Hilton.ANDREAS BRANCH/Patrick McMullan via Getty; Bryan Bedder/GettyHis season 2 arc onOne Tree Hillstarted in 2004, and two years later he appeared as Drew inthe music video for Taylor Swift’s “Teardrops on My Guitar.“Years later, when Hilton made the move to Nashville, he says the Swift family opened their home to him as he was getting his bearings in the new city.“Her dad really helped me get settled out there,” Hilton recalled, later sharing that he stayed on their family’s houseboat. “And I just ended up getting into the whole Swift family world and they were so cool.”

04of 08

He Lived on Taylor Swift’s Family Houseboat

Taylor Swift, Tyler Hilton.ANDREAS BRANCH/Patrick McMullan via Getty; Bryan Bedder/Getty

ANDREAS BRANCH/Patrick McMullan via Getty; Bryan Bedder/Getty

His season 2 arc onOne Tree Hillstarted in 2004, and two years later he appeared as Drew inthe music video for Taylor Swift’s “Teardrops on My Guitar.”

Years later, when Hilton made the move to Nashville, he says the Swift family opened their home to him as he was getting his bearings in the new city.

“Her dad really helped me get settled out there,” Hilton recalled, later sharing that he stayed on their family’s houseboat. “And I just ended up getting into the whole Swift family world and they were so cool.”

05of 08Getting a Mohawk From His ‘One Tree Hill’ Castmates — and Getting a Job Because of ItTyler Hilton in 2006 sporting a mohawk.Gregg DeGuire/WireImageBefore booking 2007’sCharlie Bartlett— where he would meet his future wifeMegan Park— Hilton remembers a spur of the moment decision with hisOTHcastmates that set the whole thing in motion.He says while the group was in a mall one day promoting the show, he askedSophia BushandHilarie Burtonif they would shave his hair into a mohawk so he would have the hairstyle for an upcoming marathon he was running. So, they walked into a barber shop, asked the barber for his clippers, and did just that.After returning to L.A., he realized he needed to let his agent know about his new look.“I called my agent and I was like, ‘Oh s—, I forgot to tell you. I shaved my head into this mohawk and is that going to be a bummer for you?’ And she was like, ‘Yeah, that’s a huge bummer for me ‘cause you’re this hair guy, and I’m pitching you as such’,” he remembers being told.He didn’t know it at the time, however, but his agent had been pitching him for the role inCharlie Bartlettbut had been told he “looks like a Backstreet Boy” and was “not right for this.““So she called them and she’s like, ‘This stupid idiot shaved his head into a mohawk, does this change it? Will you guys even see him?’ And they’re like, ‘We’ll see him. I mean, he got a mohawk, we’ll see him,'” he recalled.“And so I booked the park because of the mohawk. And there’s two kids that are alive now because I shaved my head into a mohawk randomly,” he says, referring to the kids he shares with hisCharlie Bartlettcostar-turned-wife, Park.

05of 08

Getting a Mohawk From His ‘One Tree Hill’ Castmates — and Getting a Job Because of It

Tyler Hilton in 2006 sporting a mohawk.Gregg DeGuire/WireImage

Gregg DeGuire/WireImage

Before booking 2007’sCharlie Bartlett— where he would meet his future wifeMegan Park— Hilton remembers a spur of the moment decision with hisOTHcastmates that set the whole thing in motion.

He says while the group was in a mall one day promoting the show, he askedSophia BushandHilarie Burtonif they would shave his hair into a mohawk so he would have the hairstyle for an upcoming marathon he was running. So, they walked into a barber shop, asked the barber for his clippers, and did just that.

After returning to L.A., he realized he needed to let his agent know about his new look.

“I called my agent and I was like, ‘Oh s—, I forgot to tell you. I shaved my head into this mohawk and is that going to be a bummer for you?’ And she was like, ‘Yeah, that’s a huge bummer for me ‘cause you’re this hair guy, and I’m pitching you as such’,” he remembers being told.

He didn’t know it at the time, however, but his agent had been pitching him for the role inCharlie Bartlettbut had been told he “looks like a Backstreet Boy” and was “not right for this.”

“So she called them and she’s like, ‘This stupid idiot shaved his head into a mohawk, does this change it? Will you guys even see him?’ And they’re like, ‘We’ll see him. I mean, he got a mohawk, we’ll see him,'” he recalled.

“And so I booked the park because of the mohawk. And there’s two kids that are alive now because I shaved my head into a mohawk randomly,” he says, referring to the kids he shares with hisCharlie Bartlettcostar-turned-wife, Park.

06of 08Presenting at the ‘Teen Choice Awards’Tyler Hilton at the 2004 Teen Choice Awards.Albert L. Ortega/WireImageHilton also remembered his various appearances at the Teen Choice Awards as especially nostalgic. (That layered shirt combo really says it all.)

06of 08

Presenting at the ‘Teen Choice Awards’

Tyler Hilton at the 2004 Teen Choice Awards.Albert L. Ortega/WireImage

Albert L. Ortega/WireImage

Hilton also remembered his various appearances at the Teen Choice Awards as especially nostalgic. (That layered shirt combo really says it all.)

07of 08Getting an Early Hybrid Car at Sundance Film FestivalTyler Hilton in the Volkswagen Lounge at the 2006 Sundance Film Festival.Mark Sullivan/WireImageDuring one of his trips to Sundance Film Festival in the 2000s, Hilton said he was gifted one of the “first model hybrids ever to come out,” in a gifting suite.“I feel like gifting suites were so 2000s,andearly hybrids, you know what I mean?,” he tells PEOPLE. “That was my car forever, I got it in a gifting suite.”

07of 08

Getting an Early Hybrid Car at Sundance Film Festival

Tyler Hilton in the Volkswagen Lounge at the 2006 Sundance Film Festival.Mark Sullivan/WireImage

Mark Sullivan/WireImage

During one of his trips to Sundance Film Festival in the 2000s, Hilton said he was gifted one of the “first model hybrids ever to come out,” in a gifting suite.

“I feel like gifting suites were so 2000s,andearly hybrids, you know what I mean?,” he tells PEOPLE. “That was my car forever, I got it in a gifting suite.”

08of 08Doing “A Lot” of Shows with The Black Eyed PeasTyler Hilton, The Black Eyed Peas.Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty; Carlo Allegri/GettyWhether it was “Where Is the Love?,” “My Humps” or “Pump It,” if the radio was on in the 2000s, it wouldn’t take long for one ofBlack Eyed Peas’ songs to play. During that time, Hilton remembers, he “randomly” did “a lot of shows” with the band while both acts were doing radio promo.“I feel like that was very 2000s pop radio,” he said.In a full circle moment, Hilton said he recently went to buy a used keyboard recently at a Guitar Center in Massachusetts only to find out he was a little too late.“I literally went in, I was like, ‘I saw you have this used keyboard on your website. I want to buy it.’ They’re like, the Black Eyed Peas just came in and bought it,” he said. “I was like, ‘what!?'”

08of 08

Doing “A Lot” of Shows with The Black Eyed Peas

Tyler Hilton, The Black Eyed Peas.Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty; Carlo Allegri/Getty

Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty; Carlo Allegri/Getty

Whether it was “Where Is the Love?,” “My Humps” or “Pump It,” if the radio was on in the 2000s, it wouldn’t take long for one ofBlack Eyed Peas’ songs to play. During that time, Hilton remembers, he “randomly” did “a lot of shows” with the band while both acts were doing radio promo.

“I feel like that was very 2000s pop radio,” he said.

In a full circle moment, Hilton said he recently went to buy a used keyboard recently at a Guitar Center in Massachusetts only to find out he was a little too late.

“I literally went in, I was like, ‘I saw you have this used keyboard on your website. I want to buy it.’ They’re like, the Black Eyed Peas just came in and bought it,” he said. “I was like, ‘what!?'”

source: people.com