‘Dancing with Dreams’: Country star Phil Vassar reflects on three decades in the spotlight

Country music icon Phil Vassar sits down with CTV Winnipeg's Joseph Bernacki for a conversation on songwriting, piano playing and three decades in the business.

Phil Vassar is no stranger to writing a hit single for country radio and playing the blacks and whites. He has a three-decade career of songwriting and recording those melodies on the piano.

Vassar, 63, rose to fame in the late 1990s writing No. 1s singles for country music hitmakers like Alan Jackson, Tim McGraw, Jo Dee Messina and Collin Raye before his self-titled debut album in 2000 took his career one step further.

The Lynchburg, Virginia native is currently celebrating with his 25 Years of Paradise Tour with solo shows across North America and opened for Old Dominion at Winnipeg’s Canada Life Centre on May 1.

Before the performance, Vassar took the time to sit-down with CTV News on board his band’s tour bus for a conversation reflecting on his career, half a life spent in Nashville, Tennessee and a behind the scenes look at the country music business.

“I get chills thinking about this stuff, it’s so real to me, when you can talk about these songs,” Vassar said.

Vassar grew up near the Blue Ridge Mountains in a smaller community of just over 80,000 people. He said his music inspiration drew from a melting pot of sound.

“Growing up, there was a lot of gospel, a lot of bluegrass,” Vassar said.

“The Statler Brothers were a big influence, too. They were a big band. Then, of course, right at the amphitheater in Roanoke, right near where I’m from, I caught a lot of acts like Billy Joel, saw him and rock acts like Boston and Styx,” he said. “I got to see a lot of that stuff in the ‘70s as a kid. It was a great town. Virginia is a beautiful place.”

Vassar said his father was a big influence on him musically, listening to the likes of George Jones and Merle Haggard.

“It was awesome, I mean, I grew up in a musical house,” he said.

“I’ve got two sisters, my little sister was into George Strait, and I was into Billy Joel, Elton John, the piano players; Lionel Richie, Kenny Rogers, and just so many of those guys were my big influences.”

Vassar’s father was also a singer and ran a steakhouse where he grew up. Through musical connections, the family was able to invite the likes of The Drifters, a then well-established R&B and soul vocal group to play at his high school prom.

“We had The Drifters and The Platters and The Tams, all these bands, and it was such an awesome opportunity,” he said. “We were exposed to a lot of different kinds of music.”

Bruce Hornsby, who also grew up in Virginia playing the piano was a huge influence on Vassar, notably with the release of “The Way It Is” in 1986.

“When I got his first record, it changed my life,” he said.

“I heard that record and I just went ‘The Way It Is,’ and ‘Every Little Kiss,’ ‘Mandolin Rain,’ every song on that record. Huey Lewis was one of the producers on that record and he is one of my dear friends.”

Track and field turns to songwriting

Vassar said it was experiences like this that stuck with him for years before he even thought about pursuing music as a full-time gig.

He accepted a track and field scholarship to James Madison University in Harrisonburg, Virginia where sports were his focus for much of his time in college until something changed.

“My last year in school, ‘I said, well, I’m not going to be in track, I’m not going to be in the Olympics or anything,’ so I just focused everything on music,” Vassar said.

“My track coach at James Madison, he was just a great influence, and his cousins are The Statler Brothers and he was like, ‘Look, you need to go to Nashville.’ I went along with him, and I started writing songs and meeting George Strait and George Jones, Johnny Cash and Willie Nelson.”

Getting out of college and coming to Nashville in his twenties was a big leap of faith, according to Vassar. He is self-taught on the piano, the instrument that launched his career.

“I still have that piano in a warehouse in Virginia somewhere,” he said as he laughed.

“When I went to James Madison, I ended up taking a couple of classes. My teacher was like, ‘You don’t need to learn anything here. You’re already doing what you’re going to do.’”

He saved up money at that time and was able to open his own bar in downtown Nashville. Vassar said it was overwhelming once he took an interest in songwriting and tried to get his name out there as much as possible.

“I had a restaurant club, a buddy of mine and I opened it, we had the top floor in the restaurant. Underneath, I opened up this club and my friends and I started playing on weekends,” Vassar said.

“A lot of the musicians and the writers would come in, and jam and all the record labels would come in and say, ‘Hey, man, you should have a record out.’ [I said] I’ve been trying to get a record out for 15 years, and so it just took a long time.”

He said it was a cool experience seeing Donna Summer, the band members from Styx, and others walk into their club for the first time.

“Billy Gibbons from ZZ Top lives across the street from me, and Leann Rimes was my neighbour for a long time,” he said. “Nashville’s such a great place for collaboration as far as songwriting and, I’m just blessed.”

Building momentum and writing hit singles for other country music icons

A string of success was found by the late 1990s for Vassar as he co-wrote the likes of “Little Red Rodeo” for Collin Raye, a No. 1 single in “Right On The Money” for Alan Jackson, “For A Little While” and “My Next Thirty Years” for Tim McGraw, and a pair of No. 1s for Jo Dee Messina with “Bye Bye” and “I’m Alright.”

By then, the momentum was building for Vassar’s solo career.

“Jo Dee would come into my club and sing with me sometimes, and she had ‘Heads Carolina,’ but she heard me doing ‘Bye Bye,’ and ‘I’m Alright’ was a staple in my in my bar,” he said.

“The whole place was singing it every night, and so she goes, ‘Man, who wrote these songs’? I said, ‘Well, they’re my songs’, but I wouldn’t let her cut the songs for a long time.”

Some of these tracks helped Vassar earn two ASCAP Songwriter of the Year awards in 1999 and 2001.

He said he never thought he would get a record deal with Arista Nashville at the time based on his background as a piano player. It took the influence of the artists who cut his songs to speak on behalf of the record labels to vouch for Vassar’s talent.

“Honestly, the artists they started saying, ‘Man, I love these songs,’” he said.

“They had enough power at that time just to tell the tell the label what songs they were going to cut. It was great for me.”

‘Carlene’ and ‘Just Another Day In Paradise’ make for memorable debut album

By October 1999, Vassar released “Carlene,” his first single from his debut album which became a No. 1 single in Canada and a top five track in the U.S.

Inspiration from Cindy Crawford and a story about the valedictorian from Vassar’s high school ended up serving as the basis for a song co-written by him and Charlie Black.

“I was thinking about a friend of mine, who was the valedictorian of my class and I was reading this article on Cindy and found out that she was valedictorian of her class,” he said.

“She was going to be in that video for Carlene, but the last second she was in the middle of doing all of her supermodel stuff and, of course, we’ve spoken many times since then, and she’s like, ‘I can’t believe I didn’t get to do that video.’”

With piano motifs written between several of the cuts on the debut album, Vassar found success with his first No. 1 on the U.S. charts, with “Just Another Day In Paradise,” and a few weeks later, “My Next Thirty Years,” cut by Tim McGraw became another number one as a songwriting credit.

“I wrote that song [My Next Thirty Years] in I want to say probably 10 or 15 minutes,” he said

“I had a piano in my house at that time, and I just kind of walked over to [it] and I said, ‘You know, I think I’ll take a moment to celebrate my age, the ending of an era and the turning of a page,’” he said. “I wrote it on my 30th birthday, I woke up, I wrote the song, went to the bar that night — everybody went crazy and it was just one of those things where it was almost magic.”

Five singles were released from his debut album including “Six-Pack Summer,” “Rose Bouquet” and “That’s When I Love You” which had Jo Dee Messina join Vassar for company on background vocals.

He said there was a great appetite for country music that reflected the average everyday American or Canadian back then, notably prior to Sept. 11, 2001, especially in a hub like New York City of all places. “Just Another Day in Paradise,” and Travis Tritt’s “It’s A Great Day To Be Alive,” remind him of that time.

“They set up a big stage right at the Twin Towers right there, and we would do big concerts,” he said.

“Garth Brooks was there, I was there, Blake Shelton, Jo Dee [Messina]. I think all of us were. We did every Friday. They would kind of have a take over and have huge crowds, but it was unbelievable how many folks came and they loved it.”

‘Dancing with Dreams’ and surviving a health scare

Years later, Vassar recorded a B-side he wrote years before titled “Dancing With Dreams” as an ode to the Billy Joel melodies he grew up listening to in the 1970s and ‘80s. He also traditionally ends each of his concerts with his rendition of Joel’s “Piano Man.”

He said the song reminds him of the time he got to meet one of his heroes—Ray Charles.

“I’ve lost all those guys now that we talked about in that song,” he said.

“One of my first big concerts I ever got to do was with Ray Charles, and Ray was one of my heroes, and I got to play an amphitheater in in Nashville at Starwood with him opening a show, and got to hang out with him, and we talked for hours,” Vassar said. “He was just an amazing man and the stuff he had endured in his lifetime, I just, I still can’t even believe it happened.”

A crowd favourite called “Sound of a Million Dreams,” is one Vassar will play from time to time. He co-wrote the track with Scooter Carusoe.

It features references to Bob Seger’s “Mainstreet,” and Bruce Springsteen’s “Born To Run,” with a nod to the rock and roll melodies that Vassar said were pivotal to his interest in becoming a musician.

“These songs were the story of my life,” Vassar said.

Twenty-seven top-40 singles and 10 No. 1 singles later, Vassar survived a health scare that nearly ended his life. A heart attack and a subsequent stroke in 2023 changed his perspectives on life after years of constant touring and recording.

“I was in Atlanta for six months in a wheelchair,” he said.

“I never drank and I never did drugs, and I always ate healthy. I did all the things you’re supposed to do. Six months later, I was walking and, it was amazing what they did to bring me back. Now I’m, playing with Old Dominion and we’re talking to you.”

Vassar said he feels better now than he had decades prior. However, several passings in the last few years of country music have been hard on him and have left a hole in the genre. Jimmy Buffett and Toby Keith, two of his friends and well-established musicians, passed away in the span of six months.

“They were such influences on all of us,” he said.

“I talked to Toby [Keith] before he passed and he was always just a great guy; we had so much fun. Jimmy and I, we were at the Songwriters Hall of Fame dinner together and the first song I ever really learned how to play on piano was ”Come Monday," such a fan.”

Vassar recently has been in the studio working on new music and has recorded a single “What It Means,” looking back on those health scares from three years ago.

When’s he not out on tour, he said he’s gotten back into the game of golf in Nashville where’s he made many friends along the way.

“Vince Gill was one of the first guys I ever met when I moved to Nashville and I met him on the golf course, and, it was just so wild,” he said as he laughed.

“Kix Brooks was my neighbour across the street. It’s really great to have these guys when you as an artist, really need other artists to talk to.”

Vassar said it’s incredible to see how the music landscape of downtown Nashville has changed from the time he started to where he is now.

“One day, I just started writing songs that meant something to me and those were the songs that changed my life,” he said.

“I’ve just had such a charmed life. I know I worked my butt off for it, I wasn’t given anything, but I’ve been blessed. You just have to believe in yourself.”