Chad Michael Murry - Lead
Credit: Nina Duncan

Way before we knew Chad Michael Murray as One Tree Hill’s Lucas Scott, he starred in another popular small-town-set WB drama: Gilmore Girls. For the series' first two seasons, Murray played Tristan Dugray, the popular prep school bad boy that tried to win over quintessential good girl Rory Gilmore (Alexis Bledel).

Tristan's flirting style wasn't all that mature, and he often showed his affection for Rory by dishing out sarcastic remarks and giving her the nickname “Mary” because she seemed so pure and innocent. Rory didn’t find Tristan’s advances to be appealing at the time—this was back when she was with her lovable boyfriend Dean (Jared Padalecki), and way before she fell for badass Jess (Milo Ventimiglia), after all. Ultimately, Rory developed a soft spot for Tristan after seeing his vulnerable side—and they even kissed once. But in the end, she went back to Dean and Tristan was sent off to military school in North Carolina (a nod to where Murray was heading to film One Tree Hill), leaving us all to wonder what could have been.

While Tristan was MIA for the rest of the series, we’ve had all things Stars Hollow on the brain with Netflix’s upcoming Gilmore Girls reboot in the works. So when InStyle recently caught up with Murray about his latest projects, we just had to ask the star all about his time on the series—and what it was like to play Chilton’s resident mischief-maker. “I actually really enjoyed Tristan,” said Murray. “Everyone rooted for him. He was that guy that you wanted to be close to, but you knew you just couldn’t be.”

Whether fans loved or hated Tristan, the role was memorable for Murray. “I think I was an infant when I was on Gilmore Girls,” he joked. “I was 18 or 19 years old when I did the show, which is crazy to think that it was that long ago.” And even though it was just the start of his career, the series had a lasting effect on Murray. “I created great long-term friendships with Jerry Padalecki and Milo Ventimiglia back in the day,” he said. “And they’re still friends of mine today.” And much to our delight, there’s plenty of reminiscing when Tristan, Dean, and Jess reunite IRL. “Seeing those guys really brings back old memories, and it brings up a time when we were young and just looking to see what the future would hold,” said Murray. “So that’s very, very, very cool.”

Jared Padalecki and Milo Ventimiglia
Credit: Araya Diaz/WireImage; Albert L. Ortega/Getty

Of course, Murray’s future went on to include years of starring on another series with a rabid fan following, One Tree Hill. And when we asked Murray if he would rather live in the fictional realm of Stars Hollow or Tree Hill, he carefully thought out his answer. “They’re very, very different worlds, as far as I see them,” he said, before rethinking his answer. “Actually, no, they’re not—they’re very similar, if you think about it. They’re both small towns where a lot goes on.” But there is one key difference between the two, and it’s enough to sway Murray to choose the quirky Connecticut town. “I do believe a lot less people got shot or drastically hurt on Gilmore Girls, so let’s go with that,” said Murray. “Seems like a safer environment.”