Deana Carter Celebrates 'Strawberry Wine' Anniversary, Encourages People to 'Never Quit' Brutal Music Business

Deana Carter's Did I Shave My Legs for This? is five times platinum and 25 years old. She learned to write those songs when her high school English teacher deconstructed Bob Dylan lyrics

Vince Gill dropped by Deana Carter's autograph signing at Tower Records 25 years ago when her career-making Did I Shave My Legs for This? was released. Gill was on the way home from the golf course when he turned his car around and went to the record store, where he stood in the back to observe.

Carter will never forget it.

"His presence, his gorgeous presence was such an acknowledgment, such a stamp of credibility on that project," Carter, 55, recalls. "It was crazy that news just spread by word of mouth down the Row and everywhere that Vince was at my in-store."

deana carter
Deana Carter. Mark Tucker

Two-and-a-half decades later, he's still showing up for Carter — as is much of the country music community. Gill is among the special guests — including Lauren Alaina, Ashley McBryde, Kylie Morgan, Terri Clark, Sara Evans and Martina McBride — on the 25th-anniversary edition of Did I Shave My Legs for This? The remastered album, available now, is home to her seminal "Strawberry Wine" that won Single of the Year at the 1997 CMA Awards. In a full-circle moment, Carter will present the single of the year trophy on the 55th CMA Awards, which air live from Nashville at 8 p.m. ET Wednesday on ABC.

"I was so excited [when I won] that I leaped across the stage and jumped on Ricky Skaggs, who presented the award to me," she said.

Did I Shave My Legs for This? is also home to No. 1 hits "We Danced Anyway," "How Do I Get There" and "Count Me In" – all songs that chronicled her experience.

"It was the most honest record I could make," she told PEOPLE. "It was the culmination of all my experiences. I knew it was connecting, but I'm just now starting to realize how much."

Carter had one boyfriend from 14-22 years old. She was working every job she could get to pay back her college loans. There was so much passion and emotion in writing the songs for her debut that Carter wouldn't consider recording anything that wasn't as honest as the tunes she had already written. When "Strawberry Wine" came along, she felt like the writers Matraca Berg and Gary Harrison "nailed" her life.

"I was not going to sing anything that didn't feel as real to me as my own experience," she explained. "It was unbelievable how spot-on that song was for me — and just the way God worked it out. It was meant for me to sing that song because it was my truth. And it's turned out to be millions of peoples' truth, too."

Carter said her Nashville-area high school English teacher used Bob Dylan's song lyrics as teaching tools, and through them, she learned the power in simple language. She also discovered that if she could coin a phrase in a song, she was set.

"Subconsciously, that sort of locks in with peoples' hearts," she said. "Our language has a cadence, and that's important. I think having a sense of humor about the trip-ups in life is just as important as the heartache. I just feel like every little step of my life has projected me to this place."

These days Carter wistfully recalls performing in the White House for various presidents and sitting in the Oval Office. She got to sing with Stevie Wonder and Brian Wilson from The Beach Boys. But nothing compares to the memories Carter cherishes from being on tour in the 1990s. She loved watching her artist friends and touring mates perform from the side of the stage and remembers passing other buses on the interstate and using the CB to talk back and forth. Sometimes, she said, they pulled the buses over and swapped coaches.

"Tim McGraw got on my bus before I got on his bus," she said. "It was such a family on the road. It was like the circus. That community was so loving and so important."

Now she's reintroducing the songs that brought her there to a whole new audience. Did I Shave My Legs for This? sold more than 5 million copies when it was released in 1996. The 25th-anniversary edition of the album is remastered from the original recordings and includes two bonus tracks on CD. Ten additional songs are available on the digital deluxe version of the album.

Carter wants to encourage up-and-coming singer/songwriters to keep plugging away as she did.

"This can be a brutal job," she said. "It can be a brutal business. You can never quit. There are so many examples of people that never quit following their hearts. It doesn't mean you have to take the path that other people took — march to the beat of your own drummer. Be relentless in not compromising in that area. Have a focus and a goal, and that gets you through all the bumps in the road."

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