How one night at City Winery ended in accidental interviews with two Nashville powerhouses

Good things come to those who wait. Or, as in my case, after a last-minute ticket cancellation turned into a wonderful night that I wasn’t expecting….

For Charles Esten to spend the eve of the Nashville series finale in New York felt nothing short of serendipitous for this longtime Nashie. Going to a Nashville cast concert in New York became a ritual every year from my freshman year of college all the way up to last year’s show, post my graduation.

This was my fifth time seeing Esten perform, but it was the one time that allowed him to dig deeper into his character’s emotional songbook from all six seasons. From “No One Will Ever Love You Like I Do,” to “Playin’ Tricks,” and the thrice-television-performed “Like New,” Esten weaved semi-acoustic versions of every fan’s favorite songs with stories about production.

For one, Esten shared that the Academy Award-winning creator of Nashville, Kallie Khouri, asked to use the title of a song he co-wrote. In between seasons, Khouri decided Esten should sing that song, “I Know How to Love You Now,” during the live broadcast portion of the show’s season three premiere.

The night showed that Esten’s voice is not one created from Hollywood studio tricks. Rather it is awesomely raspy, sometimes twangy, but always seems to call back to a Nashville before it gave way to rappers and electro-country. Perhaps, that’s just how the producers wanted it. After all, his character, Deacon and late-wife Rayna Jaymes (played by Connie Britton) — who may or may not appear on the series finale — are supposed to be veterans of the business.

Little did those producers know the casting would be so powerful as to make a country music star out of a former improv actor. To hear his fans discuss their loyalty — many are following the singer-songwriter to a show in Boston tonight (July 26th) — is to hear Esten talked about as if he were Dwight Yoakam or Vince Gill. And to these people, he is.

To that end, guitar tech and Nashville prop master Danny Rowe explained to me in a post-show interview that Esten is always thinking about his fans from the stage, saying, “Everything is done in such a giving way. He’s really thinking about how to best put a set together to really entertain the crowd. He’s not selfish about the songs he picks.”

In fact, Esten’s love for his fans embodies selflessness: He spent over an hour meeting and greeting fans who had stuck around after the show. He did not have to do it, and it wasn’t planned. He genuinely loved saying hello to everybody. He stuck around until the last fan left and took as much time with each person as they wanted.

Esten sticking around is the reason I was able to strike up a conversation with Mr. Rowe. We all hung out, and he let me roll tape. Rowe, who’s role spanned from giving actors bits of business with their music equipment to tour roadie for all Nashville cast outings, says he knows what’s coming in tonight’s (July 26th) series finale, but won’t spill the beans.

Rowe did expound on his thoughts about why acclaimed producer T-Bone Burnett moved on from the series early in the run. “T-Bone is certainly is the man with the golden ear. He’s someone who never really does repeat, follow up records,” Rowe explains. “He moves on from one thing to something new and cool. He’s kind of a trailblazer in that way. And I always felt that he kind of help set the chessboard and then was able to move on. At least, that’s my guess.”

One man who has not moved on from the music of Nashville is Colin Linden. Linden, who Rowe introduced me to backstage, “voices” Deacon’s guitar. Linden accompanied Esten at this show, as he has on all of the various cast members’ live dates and group tours. On this evening, he played a range of electric and acoustic string instruments. Speaking from the green room, Linden said the commitment of the cast to the craft is what keeps him coming back for more.

“The thing that I’ve found that continues to blow me away, is how much the cast continues to invest in these songs,” Linden reveals, “And the lines get blurrier between them as individual musical artists and the characters they played. They just have such incredible commitment to this music.”

When I asked about Charles Esten’s transformation from ‘Chip’ Esten, the improv star (known to my generation of the theatrically inclined for Whose Line is it Anyway?) to Charles Esten, country music star, Linden had one word to say: “Fearlessness.”

“I remember, we played at the Opry pretty early on. I think we were going play a song he had written that afternoon. I said, ‘That’s amazing that you feel so comfortable to just kind of come in out of the blue and play the song at the Grand Ole Opry that you’d never played before,’” Linden explains.

“His response to me was, ‘For several years, a stranger would yell a topic out to me, and I would have to make up a funny song about it on live television. This is nothing.’ And he’s just fearless like that. And in that way, he’s kind of been the guiding light for all of the cast to be free about that.”

Fearless. What a word to describe everything about Nashville, the TV show (and the city it portrays). Six years of fearless actors, fearless music and world-class musicians, and fearless country music drama that draws to a close tonight on CMT.

Congrats also go to Esten for setting a Guinness World Record for “Most Consecutive Weeks to Release an Original Digital Single by a Music Act.” The actor-turned-singer has made history by releasing a single for 54 consecutive weeks since July 2016. He also recently played the Grand Ole Opry for the 100th time.