The first time Chris Young performed solo in front of Brenda Gregory’s class on a Friday as a high school student, she didn’t have many words.

“I’ll never forget it. I think the whole class and I just went ‘Wow,’” Gregory recalled.

Young was a freshman at Oakland High, where Gregory taught prior to Siegel’s opening. As a freshman, he won the role of Riff, leader of the Jets in “West Side Story.”

“Everyone was mad that I cast a freshman in that role,” Gregory said.

The two reunited last week to tape a segment with Siegel High's Chamber Choir for the 57^th Annual Country Music Association Awards. During the segment, which aired Wednesday during the awards show, they talked about Young’s theatrical beginnings, the early days of his career and what life is like now.

“Somebody told me once that if I wanted to be an artist, that I had to learn how to be one,” Young shared.

He began writing songs as a young teen — “I was not very good,” Young said — and still does so daily, either solo or in a session with others.

“You don’t have to find as many songs if you can write them yourself. I’ve probably written 90 to 100 songs just this year, even with all the touring I’ve done,” he said.

Near the end of his visit, Young presented Gregory with a brand new Chevy Trax.

Young thanked Gregory for her role in developing him as a performer, even if he didn’t end up on New York City’s Broadway, as many of his teachers and classmates thought he would.

“You pushed me to learn things that I never would have gone to look for myself,” he said, referring to audition pieces for midstate and state competitions. “You made me a better singer even when I wasn’t singing classical music.”

Young recorded his first independent album while still attending Oakland and gave copies of the record to his friends as a graduation gift. It was another few years before he’d win Season 4 of Nashville Star in 2006 and sign with RCA Nashville.

“It was a long time, but you give up or keep going,” he said.

Since then, Young has released eight albums and was inducted into the Grand Ole Opry in 2017.

Young attended Belmont and MTSU before his career took off. In 2021, MTSU celebrated the opening of the Chris Young Café, a rehearsal space and performance venue for students in the College of Media and Entertainment. He has given back to the university by donating equipment used on his tours, created a scholarship for recording industry students and served as a commencement speaker in 2019.