The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (2024)

Tyler Hilton lived it up in the 2000s.

The multi-hyphenate, who starred on One Tree Hill as 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's Walk the Line.

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

Following the conclusion of his Giving It All to the Night tour and the release of his EP "No Land's Man" on August 2, we asked him to list the absolute most aughts things that happened to him in that memorable decade.

01of 08

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

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (1)

Back in 2005, when Paris Hilton's cell 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. "Very 2000s."

02of 08

Appearing on 'TRL' — Multiple Times!

When thinking back on the late 1990s and early '00s, its impossible to ignore the phenomenon that was MTV's TRL. Hilton appeared on the show on various occasions including one 2006 episode that featured several of his One Tree Hill castmates — and special guest Beyoncé.

03of 08

Opening for Hilary Duff

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (3)

Though many knew Hilton from his role on One Tree Hill, he was a musician long before he considered himself an actor. In 2005, he opened for Hilary Duff's "Most Wanted" tour (so yes, he got a front-row seat to "Come Clean" every night).

04of 08

He Lived on Taylor Swift's Family Houseboat

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (4)

His season 2 arc on One Tree Hill started in 2004, and two years later he appeared as Drew in the 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 08

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

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (5)

Before booking 2007's Charlie Bartlett — where he would meet his future wife Megan Park — Hilton remembers a spur of the moment decision with his OTH castmates that set the whole thing in motion.

He says while the group was in a mall one day promoting the show, he asked Sophia Bush and Hilarie Burton if 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 in Charlie Bartlett but 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 his Charlie Bartlett costar-turned-wife, Park.

06of 08

Presenting at the 'Teen Choice Awards'

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (6)

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

07of 08

Getting an Early Hybrid Car at Sundance Film Festival

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (7)

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, and early hybrids, you know what I mean?," he tells PEOPLE. "That was my car forever, I got it in a gifting suite."

08of 08

Doing "A Lot" of Shows with The Black Eyed Peas

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (8)

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 of Black 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!?'"

The 8 Most 2000s Things to Happen to 'One Tree Hill''s Tyler Hilton, from Living on the Swift Family Houseboat to Experiencing Paris Hilton's Phone Hack (2024)
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