Chely Wright came a long way to her Wednesday night gig at City Vineyard

Chely Wright "I Am the Rain"

Chely Wright's show Wednesday night at City Vineyard was way out of the ordinary—no surprise in that Wright herself is way out of the ordinary, having not only moved from a successful country music career in Nashville to her acclaimed pop singer-songwriter residency in New York while making history in the process.

To be sure, Wright sang her big country hits, most notably her first Top 10 "Shut Up and Dance," from 1997, and her 1999 chart-topper "Single White Female." She also recounted her childhood growing up in the small town of Wellsville, Kansas, in a "country music household" where she liked the likes of Loretta Lynn, Connie Smith and Conway Twitty (and the Beatles, whom she thought were "a weird country band") and knew she would be a country singer by the time she was five.

Her parents were supportive: "They said, 'Get good grades and stay out of jail!' and so far I've been successful—but the night is young," said Wright, continuing her story with her move to Nashville in 1989 and singing in a country music show at the then Opryland theme park adjacent to the Grand Ole Opry House. It was on Sept. 16 of that year that she first performed on the Opry stage, after Roy Acuff recognized how nervous she was ("I was afraid I'd throw up!") and sat on a stool next to her to calm her down. But the late Opry great who really took her under his wing was Porter Wagoner.

"I caught his attention and he mentored me—and wanted me be his 'girl singer,'" she said, noting that the term "might be a pejorative today," but back then she couldn't have been happier. "I went on the road with him and learned how to perform from him—and he saw potential in my songs and was incredibly helpful."

One day at Wagoner's house, Wright related, he presented her with a guitar—one he said had belonged to his late 1960s/early '70s girl singer Dolly Parton.

"I was 90 percent sure it was Dolly's, but Porter was getting on in years, and one day I was working with Steve Buckingham—Dolly's producer and best friend—and told him about it. He called Dolly up and said he was with me, and I heard her say 'Hey, Chely!'—which is something you don't forget!—and told her about the guitar. She asked him to describe it, and he told her it was an old gut string acoustic with pink and orange flowers shellacked onto the body. She said, 'I wondered where that old guitar went!' So I told Steve to ask if she wanted it back, and she said, 'Tell her to keep it! That old guitar's got a lot of new songs in it.'"

Indeed, Wright played a number of new songs at City Vineyard, many from her new album I Am the Rain and including "You Are the River" (co-written with Edie Carey the modern way, she said, via text message and voice memo), "Where Will You Be," "Holy War" and "Pain."

Recognizing the melancholy nature of such titles and song content, she addressed the audience: "You're probably asking yourselves, 'Are all of her songs sad?' Yes, they are!" She then recalled how, after submitting new songs for her next country record to her Nashville label, the response was, "If you don't write something positive and hopeful, we'll have to put on a warning label so people won't kill themselves!"

But there was a big reason for Wright's admittedly depressing songs, one that led to what she called "a breakdown—clinical depression," but what she now calls "a breakthrough."

"The long and the short of it was that I was in commercial country music—and in the closet," she said. "It was a tough spot to be in."

It was now 2006. Wright, who knew she was gay when she was nine, had "made a deal with God" when she went to Nashville, she said, committing herself to love only music.

"But cutting a deal with God at 19—it shouldn’t be binding!" she added, then related how she really didn't know much about love at the time, and only after a failed closeted relationship ("nothing grows in a closet—maybe mold, but certainly not love") realized that if she were to find love again, it, too, would fail.

"So I decided to come out of the closet and write a book about it."

Sure enough, Wright became one of the first gay country artists to come out of the closet in 2010--the year her autobiography Like Me: Confessions of a Heartland Singer was published.

"Now I wake up every day and the black cloud gone," she said, "and the upside was that I wrote a ton of songs!"

Some of those songs first surfaced on her Rodney Crowell-produced album Lifted Off the Ground, which was released in 2010 around the time of her memoir's publication. I Am the Rain, which was released late last year, was produced by another luminary, singer-songwriter/producer Joe Henry.

"He's a producers' producer, artists' artist and writers' writer," said Wright, who was softly and subtly backed on saxophones at City Vineyard by Henry's multi-instrumentalist son Levon Henry. Late in the set she switched places with him so he could play guitar and sing a song from his new album Sinker.

"We've got to make sure we keep our young artists and support them by buying their records," she said. Reflecting on her own younger days touring the U.S. with her band, Wright, who is an outspoken progressive critic on Twitter, voiced her love of America in her lead-in to new album track "Mexico."

"I was lucky to be able to see a lot of the country," she said, noting that "Mexico" concerns her fascination with truck stops and those who inhabit them—particularly at 2:30 a.m. She closed with "Single White Female" after noting that she never tires of singing the same song "over and over and over," as she's so often asked.

"A songwriter works to be able to play a song over and over and over!" she said.

Wright's gig was part of the "Voices on the Hudson" songwriter seres at City Vineyard, which is situated on the banks of the Hudson River at Manhattan's Pier 26.

"New Jersey's never looked so good!" she said, looking across the Hudson through the windows behind her in the corner of the nightspot. Now living in Manhattan with her wife and twin boys, she's followed in the footsteps of Rosanne Cash in leaving Nashville and a major country music career and creating her own singular music niche in pop, while also retaining a remnant of twang.

Like she said to a gal in the audience who actually hailed from the Wellsville, Kansas, area, "We got out, didn't we?" In her case, Chely Wright got out and has since come a very long way.