Conan O’Brien Delivers a Hilarious Performance as a Talent Manager in Dawes’ New Music Video—Watch Now! .Linh

The music video begins with Taylor looking for his audition spot as he enters an abandoned building. He then sees O’Brien sitting at a desk and eagerly welcoming him in.

Taylor thinks it’s the spot he’s meant to be at, so he begins performing and listening to O’Brien, who instructs him to dance and do an array of strange things, like playing the flute and wearing a pink boa.

As O’Brien begins filming him with a camcorder, Taylor starts to get confused but finishes his performance.

After asking O’Brien how he did, he says, “I don’t know. I’m not really a music guy. You should move on now. I got my film,” and Taylor walks out of the building only to realize it’s not where he was meant to be.

The musician tells PEOPLE that he approached O’Brien to participate in the music video after performing with him at the Newport Folk Festival, where they became “fast friends.”

“I reached out to see if he’d be interested and he graciously jumped onboard. He’s truly one of the kindest and THE absolute funniest person I’ve ever met so this was quite an amazing experience for us,” he says.

In addition to the new album, Taylor is also celebrating the arrival of his third baby, daughter Louise “Lou” Everett, with his wife Mandy Moore.

“She’s perfect and we’re all pretty obsessed… especially her big brothers. While this video is being released, I’ll probably be at a park somewhere chasing our toddler boys in two different directions while Mom brings baby Lou up to speed,” he tells PEOPLE.

“We’ll be on tour for a lot of November and December (and then again in April) to support the new album Oh Brother (our 9th!),” continues Taylor. “Conan isn’t coming along, but I’ll give his phone number to anyone that buys a ticket.”