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The pair appeared on the teen drama as Dan Humphrey and Nate Archibald, alongside the likes of Taylor Momsen, Blake Lively and Leighton Meester.
And a whole eight years after the show came to an end, the pair have now met up to reflect on the gig, and what they've been up to since.
"I know that I watched with my now wife, with Domino [Kirke], before we got married. It must've been six months after we met," Penn said.
"She had never seen it, and that's the last time I can remember seeing an episode. I remember even then, it has nothing to do with the show, but it was very hard to watch.
"These snapshots of yourself when you're 20, 21, 22 years old. Who can enjoy that? Sometimes it's just uncomfortable"
Laughing, Chace agreed: "Buddy, you have to strap me to a gurney and pop my eyes open like Clockwork Orange," before conceding: "But no, it would be interesting to see the first couple maybe."
As the discussion continued, the duo decided that maybe watching themselves back alongside the rest of the cast wouldn't be so bad, after all.
"To go back and open that time capsule, I think there would be some nostalgic value," Chace said. "We're doing that when you come to L.A. We'll have a drink.
"A little watching party. Dude, if we live-tweet a viewing of any episode of Gossip Girl, people would love that," Penn replied.
Too right we would!
As well as making exciting post coronavirus plans to look back at the series, the pair also chatted about their subsequent gigs, in Netflix's You and Amazon Original series, The Boys.
They were the first to admit that boy their roles were in stark contrast to teenage heart-throbs, Nate and Dan.
Chace plays Kevin, The Deep in his Amazon series - a vapid and somewhat disingenuous superhero - while Penn plays murderous stalker Joe in Netflix's You - a character who, despite swooning and adoration from some viewers, is unquestionably an evil sociopath.
"It's interesting to me, because also, man, to be honest, we move on from Gossip Girl to playing despicable white male privileged guys," Chace pondered.
While looking at their new roles, Penn added: "They're both shows where immediately they take the trope they're working with - in your case it's a superhero and my case I guess it's like the romantic male lead - and then basically within the first episode it's bludgeoned it with a sledgehammer.
"It's like, we've seen the happy, sweet, saccharine stuff, and now we're looking to deconstruct it all, because we see how it hasn't served us maybe."
If Nate and Dan are responsible for Joe and The Deep then we can't wait to see what the boys do next...
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