Singer-Songwriter Jesse Winchester’s Wife Insisted on a New Album

Love Filling Station Is His First Studio Album in a Decade

Since releasing his self-titled debut album in 1970, Jesse Winchester has quietly written a catalog of songs that earned him a Lifetime Achievement Award from the American Society of Composers, Artists and Publishers (ASCAP). Along the way, he’s recorded a series of albums that has influenced a generation of younger songwriters.

That influence was acknowledged during a recent taping of Spectacle: Elvis Costello With …, a Sundance Channel series that features Costello performing and having discussions with a wide variety of songwriters and musicians. The episode, which airs Wednesday (Dec. 16), features Winchester and Costello performing Winchester’s “Payday” with a cast that includes singer-songwriters Sheryl Crow, Neko Case and Ron Sexsmith.

Although Winchester’s music is infused with folk, country and rock ’n’ roll, the closest thing he’s had to a major country hit are the Mavericks’ “O What a Thrill” (1994) and Michael Martin Murphey’s “I’m Gonna Miss You, Girl” (1987). However, many of his compositions have been popularized by other artists, include “Biloxi” (Jimmy Buffett), “Let’s Make a Baby King” (Wynonna), “Mississippi, You’re on My Mind” (Jerry Jeff Walker), “Brand New Tennessee Waltz” (Joan Baez) and “Rhumba Girl” (Nicolette Larson).

Winchester included “O What a Thrill” on Love Filling Station, his latest album and his first studio project since 1999’s Gentleman of Leisure. Recorded in Nashville, it features appearances by bluegrass vocalist Claire Lynch and Dobro player Jerry Douglas. In an interview with, he talked about his career and the album.

The story goes that you finally relented in releasing a new album because of your wife’s insistence. What did she say to you specifically to get the point across?

Winchester: How do I sum up a couple of years worth of … what was the word you used? (laughs)


“Insistence” is good.

That’s better than “nagging.”

It’s a lot better than “nagging.” That’s exactly what I was looking for — an alternative to that word. I don’t how to sum it all up briefly, but she said, “Jesse, you need to put out another record.” My wife sells my CDs at my performances, and she hears what the people say. Apparently, a lot of them were saying, “Oh, I’ve already got that CD. When are you gonna make a new one?” Finally, I listened. Eventually, one drop of water can wear down a boulder if you give it enough time.

You’ve had a successful career, but it seems like you’ve never really been attracted to the bright lights and glitz of show business.

I might reverse it and say they haven’t really been attracted to me.

What were your expectations when you recorded your very first album?

I think it’s kind of like buying a lottery ticket. I don’t do that, but I’ve had friends that do. And every time they buy one, they think they’re gonna win. They’re convinced they’re gonna win. It’s a little bit like that, I think. It can be discouraging when you don’t win.

Do you feel like you’ve won?

Yes, I do, but I’ve had to get kind of philosophical about it. Maybe the Lord didn’t bring me that red bicycle, but He taught me patience. (laughs)

Gentleman of Leisure had a lot of tracks with strong electric backing, but the new album is very much acoustic-oriented. Your music seems adaptable to a wide range of instrumentation. Has your attitude and approach to the songs changed through the years?

It has, but I think with this last record, there was a lot of making a virtue a necessity. The necessity was a small budget. It sort of forced me to make a record that I at least envisioned toward an acoustic, bluegrass kind of thing. Certainly not bluegrass in content, but bluegrass in philosophy, simplicity, classically-country instruments and especially to forego using a big drum set.

In my heart, I’m still trying to write hit records, oddly enough, and mostly failed. But the idea all along for me has been to do what my heroes did — which was to write and record great singles that everybody liked to hear on the radio and dance to and fall in love to. That’s always been the idea.

The album includes three cover songs. What was the process of choosing those?

“Stand by Me” is, I think, my favorite song in the world. It’s just so powerful and simple. It’s just the standard chord change that a million pop songs have been written to. It allows the singer to just say exactly what you want to say to your lover. It’s my favorite song, I do believe.

The others, I love Terry Smith’s song, “Far Side Bank of Jordan,” because it combines gospel with a human love song. It just covers all the bases in one song — God and woman. I love it for that reason. Then the “Loose Talk” song, I wanted to do something with Claire. I love that “Loose Talk” song. It’s funny, in its own way, about people dealing with small-town gossip. It’s just so human that way.

Had you known Claire prior to recording it?

We have done shows together quite a bit. … We became friends that way. Really, until that started happening, I didn’t know Claire’s music. She just has such a beautiful band. It’s a wonderful sound they get. So clear and so elegant.

You said you wanted to make hit records that everybody would listen to. Have you ever sat down and consciously tried to write a song that could be pitched to a mainstream artist?

I have written to order a couple of times. I’ve never been hugely successful at it. I’m one of these people that sort of has to rely on the idea coming to him, rather than reading a newspaper or scouring or eavesdropping on people’s conversations to get ideas. I have to get my ideas from who knows where — just out of the blue. That sort of limits me in my content. I can’t sit down and say, “Well, Brooks & Dunn or whoever are looking for up-tempo, positive lyrics.” I’m not good at that.

You seem so relaxed and comfortable onstage, but I’ve always heard that touring isn’t one of your favorite things to do.

That used to be true of me. After I took a break of about 10 years from performing in the ’90s, then I made a record with Jerry Douglas producing. I had so much fun, I decided I owed it to myself and everybody else who worked on it to promote it. So I went back and performed again. And, lo and behold, I discovered I was having the time of my life. I don’t know what caused the change, but I’m very grateful.

You have no idea what the difference was?

I think it’s that when you get older, people are somehow more forgiving or nicer to you. I really don’t know what. Or maybe I learned something. … I can’t account for it, but I enjoy it very much these days. I mean, I don’t think I’m ever going to enjoy returning a rental car or running through the airport.

Calvin Gilbert has served as’s managing editor since 2002. His background includes stints at the Nashville Banner, Radio & Records and Westwood One.