“I closed my eyes and I thought Frank Sinatra was singing on stage,” Coach Snoop Dogg said.

It takes a lot of gumption to sing a song made famous by Frank Sinatra — a song called “Send in the Clowns” — without worrying that you’ll end up looking like a clown for trying to live up to Ol’ Blue Eyes. But, during the Knockouts of Season 26 of The Voice, singer Edward Preble wowed the Coaches with his cover of a track that’s a lot more of an oldie than most of the songs you hear on the show.

Preble, who joined Team Bublé following his Blind Audition, was up against two other talented singers, 17-year-old Shye, and 38-year-old J.Paul. Despite only being 19 years old himself, Preble explained that he was a fan of classic music of the sort Sinatra used to sing.

“I want to show the younger generation this music,” Preble said ahead of his performance. “If I’m able to do that and then one day I can look around me and there are lots of different crooners and jazz singers, that would make me very happy.”

As befitting an oldie like “Send in the Clowns,” Preble’s performance on The Voice stage wasn’t overly flashy. Instead, the young singer channeled his best Sinatra.

The Voice‘s “Send in the Clowns” Knockout Showcased the Sinatra Classic’s Regretful Lyrics

“Isn’t it rich? Are we a pair? Me here at last on the ground; You in mid-air,” Preble began. “Send in the clowns”

The song, which was originally written by Stephen Sondheim for the 1973 musical A Little Night Music, gained a second life as a popular ballad when Sinatra recorded a cover that very same year. It’s a soulful bit of whimsical self-pity, as the singer reflects on life’s little disappointments and how they’ve been made out to be a fool.

“Isn’t it rich? Isn’t it queer? Losing my timing this late in my career?” Preble concluded. “And where are the clowns? There ought to be clowns. Well, maybe next year…”

“I closed my eyes and I thought Frank Sinatra was singing on stage,” Coach Snoop Dogg said.

Preble did not win the Knockout — Coach Michael Bublé gave that honor to Shye and her cover of Katy Perry’s “The One That Got Away” — but unlike the singer in “Send in the Clowns,” he had nothing to wallow in. Reba McEntire used her one steal to snatch Preble up, advancing him to the Playoffs.

McEntire, who said that Preble had “such a mature soul” for still being in his teens, was excited to have the crooner on her team.

“I loved Edward from the very beginning,” McEntire said. “He is a character, he’s got a great sense of humor… it’s going to be fun working with him.”