When Lee Ann Womack promised her City Winery audience a night packed with miserably sad country songs, she made good on that all night long. But before that show on Friday night (Oct. 4) -- night one of her two-night stay at the Chicago venue -- I had the chance to talk to her backstage about said miserable songs.

First, though, we talked about firsts.

The first time Womack every bought an album with her own money, it was Steve Wariner's Midnight Fire from 1983.

The first time Womack felt like she'd really made it was right after her first couple albums came out in 1997 and 1998. "I was sent out to LA to read the ACM nominations with LL Cool J," she told me, "and they put me up at the Beverly Hills Hotel. I had never ever stayed at, been to or even seen anywhere like that. I had my cousin with me, and we were both just like mouths open wide. I felt like I was on my way, for sure."

The first country artist she ever loved, even as a kid, was either George Jones or Dolly Parton. "With Dolly especially, it wasn't so much about a song as it was just her," Womack said.

So after growing up around church music and all that traditional country music, and after turning 30, Womack had the chance to release some music of her own.

And what Womack has learned after making nine albums -- since her self-titled debut in 1997 -- is that she's at her best when she's at her best.

"The last couple records I've made, and the shows that I've played, have been by far the most happy times, the most fulfilling and rewarding times, I've had in the business at all," she told me. "When you're making music that you really love, and you're making it for yourself instead of a record label or radio, that's when I'm a lot happier.

"I knew that all along. But once I started making records for different reasons, I wasn't nearly as happy."

She still listens to country music for pleasure, but not necessarily what is on the radio. "Pop country is not what I listen to. It's just not what I like," she said, adding that even as a young girl she was drawn to more serious songs. "I think it's more the emotion in it than the actual subject matter. To sing about those kinds of things, you have to come from a certain place. And that's what I connected with then and still do."

Womack's set list from the show seamlessly blended her older songs with newer ones, all from the nearly 23 years in the music business. With “Does My Ring Burn Your Finger, “Never Again Again," “Last Call," “Hollywood, “Solitary Thinkin’," “A Little Past Little Rock," “All the Trouble, "I Hope You Dance," and so many more.

Around the halfway mark, she told the crowd it was time to head down to the Central Baptist Church. She brought her band to the front of the stage for her timeless rendition of "Wayfaring Stranger."

And before she did "Chances Are," she shared the story behind the song and how she's still a little salty. "Hayes Carll wrote this song. We were nominated for a Grammy. We lost," she said. "Still pissed. But we're gonna do it anyway. So here’s a losing song." The Grammy for best country solo performance in 2016 ultimately went Chris Stapleton for "Traveller."

P.S. Of course, I had to go a little off-topic and ask Womack about her #NationalSewingMonth Instagram post. "I do it all the time. My sewing machine is set up in my hotel room right now," she said. "It's cool because I can buy things at vintage stores and kind of remake them. I think it's a really good skill to have. If Anna (her 20-year-old) wants blue velvet curtains for her room, I can have them done by tomorrow. That's what I love. Most of the patterns I buy are vintage. I order those on Etsy, from the '60s and '70s. I really lost interest in going to stores and shopping and seeing 20 of something hanging there. I love being able to have things that nobody else has."