25 Years Later, Deana Carter Still Never Gets Tired of Singing ‘Strawberry Wine’

Songwriting legend Ray Wylie Hubbard once said that there’s an important question you need to ask yourself after you write a song: Can I sing this for 25 years?

That point may not be at the forefront of young artists’ minds while they’re focused on landing their first big hit. But if they’re lucky, they’ll one day have a hit so big and beloved that they can’t play a show without singing it, and for Deana Carter, that song is ‘90s country classic “Strawberry Wine.” Though she didn’t write it, Hubbard’s advice still holds true for Carter and her biggest hit, which she first put out in August of 1996 as part of her landmark debut album, Did I Shave My Legs for This?

On Friday (Nov. 5), Carter released a 25th anniversary deluxe edition of Did I Shave My Legs for This?, including two versions of “Strawberry Wine”: A remastered version of the original, and a 2021 version, including guest vocals from Lauren Alaina, Ashley McBryde, Martina McBride and Kylie Morgan, plus guitarwork from Vince Gill.

“It was really special to see them…I was there through the whole process. If they were singing, I was emotional,” Carter explains, adding that re-recording “Strawberry Wine” was particularly powerful when she watched the artists from a younger generation singing her song.

“Like, Ashley [McBryde] has this crazy, amazing mountain range [voice], when she hit [the high notes] in ‘Strawberry Wine’, and it had this yodeling, smooth sound to it, I just burst into tears,” she continues. “It caught me so off guard that I would be so moved by a song that I’ve heard probably five billion times — coming out of myself and on the radio or whatever.”

Part of the reason that Carter was so moved by the experience was because it was clear that each artist on the new recording had her own long-standing relationship with “Strawberry Wine.”

“You know, it wasn’t the first time they had sung it,” she reflects. “In other words, it was something that might have influenced or encouraged them along the way. It just was really emotional for me.”

As for her own relationship with her hit song, Carter says she never gets tired of performing it — whether in the studio for special versions like this one, or live in front of a crowd.

“No, never,” she says. “I love it….You sing a song, whether you wrote it or not, that is the most true for you that it could ever be, so that you can repeat it night after night and be authentic. You know, when I sing that song, still, I go through memories of the house I grew up in. I go through my brother being little, like, in third grade. I go through going on dates in high school with my best friend, Connie.

“There are so many things that go through my mind surrounding the truth in that song for me,” she reflects. “I get to re-live the creation of something so special every time I go onstage. It’s just such a blessing. It never gets old. Never, never gets old.”

The 25th anniversary version of Did I Shave My Legs for This? is out now. On November 18, Carter will headline a special one-night-only show surrounding the project at Nashville’s Ryman Auditorium.