The Dream

“Our barometer was if this was the last record I get to make, we should make something that we're proud of,” Hailey Whitters tells Apple Music of The Dream, an album that reflects her spirit of self-determination following a period of professional disappointment. The “we” that the Iowa-bred Nashville transplant refers to is a team of two—Whitters and her boyfriend Jake Gear—who co-produced a dozen-song set deftly uniting time-tested country forms, contemporary rhythms and references, and sharpened singer-songwriter perspective. Up until then, she’d quietly released music but had more success writing songs for other acts, and he’d presided over business dealings in music publishing. “I think the fact that we were both so ignorant to the whole process, it really freed up a lot of the expectations on the project and we just got to explore without fearing too much of failing,” she explains. “I feel like this whole process, and everything that's come from this record, has really just given me my spirit back. It just reminded me why I got into this business in the first place.” Here Whitters tells the stories behind each of The Dream's songs.

Ten Year Town
“Everyone has the ‘Ten Year Town’ song, just because it's such a commonly used phrase when talking about Nashville. It was meant to be written with Brandy Clark—she's another artist that I admire so much and she also is somebody who's been in town for a while and I know had moments of frustration and struggles. ‘Confessional’ is a great word for it, because it just felt like we were writing down a page in a diary or something. From a production standpoint, we wanted it to sound just totally stripped. It's me and Kris Donegan is playing guitar on it, and we just wanted it to sound exactly like me sitting on the edge of the bed singing the song with me and my guitar and coming from this broken, frustrated spot. Jake and I definitely wanted it to be the first song that people heard, just because that is where the whole journey started for me two years ago, making this record. ‘This next song could turn it all around’ is the last line in the song. I think it's really ironic, because it literally is the song that I feel like turned everything around for me.”

The Days
“I wrote that song with Hillary Lindsey and Ben West. As far as the rhythmic point element of that song, that's totally Ben West. We took that demo into the studio as the bare bones and just said, ‘Hey, everyone, just add in here where necessary.’ Time is a very important element in this concept of the record. In a way, I feel like I gave up on myself a little bit as far as having a career in music. It really opened my eyes to this whole side of life that I had not been noticing, because I'd been so tunnel vision on my career for the last 15 years. I really was feeling that there's this whole life that is happening outside of Nashville and outside of the record industry. I just felt like it was very important to be paying attention to it and realize just how lucky we are to be here and to have time.”

Red Wine & Blue
“I was drinking red wine out of a Solo cup on the 4th of July and that title just popped into my head. I took it to Jessie Jo Dillon and Brandy Clark—we started that song in the daytime and then got back to finish it one night. We honestly were just sitting there late into the night, drinking red wine, and Jessie's going out and chain-smoking cigarettes, and it felt really cool. It's this love story about this girl falling for this guy out in Hollywood. I feel like it's a girl just singing alone in this big, old empty house and the sun's out there shining and she's just sitting at the piano getting drunk on wine. We wanted it to feel a little more raw and less polished.”

Dream, Girl
“I wrote that song with Dustin Christensen, and I came in with the title ‘Dream, Girl.’ I had seen it in a magazine. I feel like that kind of topic is totally out of Dustin's wheelhouse, but he's so good at that ’80s synth [sound]; I call it ‘disco country.’ It's a light concept, but I really loved the idea of saying to this girl, trying to build her up, ‘You're someone else's dream, girl.’ For me, it feels that way a little bit with the industry and the struggle to try and please the industry.”

Loose Strings
“Whenever I come across a song and decide to cut it, it's usually a song that I'm jealous that I didn't write. That's how that song was. I remember hearing Brent Cobb's work tape and I just put it on repeat. I was obsessed with his phrasing—the melodies and the lyrics. I've had people come up to me since hearing my version and they're like, ‘Wow, I had never even considered that from a female perspective.’ That's something I like about great songs is that they can defy genders.”

Heartland
“That's the turning point on the record. I was finding myself going back home a lot, both mentally and physically, and just really longing to get back to my roots and who I was when I got here. So that song feels like a coming home in so many ways for me. It's my love song to where I'm from.”

Janice at the Hotel Bar
“I was writing with Lori McKenna and I came in that day and said, ‘I would really love to write a song of what a grandmother or an older woman would say to a younger woman about life.’ Lori asked me if I knew who Living With Landyn was, and I had no idea who she was, but she's this big Instagram influencer. A few months prior, [Landyn] had spent several hours in a hotel bar in New York City with a complete stranger, an 80-something-year-old woman named Janice. Janice just started dishing out these little bits of wisdom about life. Landyn had posted a photo of her and laundry-listed some of the topics, like 'sardines' and 'berries,' 'men are babies,' 'granddaughter still single.' My grandma always told me a glass of red a day is good for your heart. There's a woman in my hometown, she's 95 and she still mows her own lawn and puts up the best Christmas light display in our whole town. We just started pulling things from our own lives and putting it all together in that song.”

Happy People
“Little Big Town had done their version, Lori had done a version, so I honestly was feeling a little stunted on where to go direction-wise. Jake really reimagined that song in a way that I feel like is so unique. The key change and the harmonica, it just feels really bright and happy.”

The Devil Always Made Me Think Twice
“Jake was a publisher at Sea Gayle Music at the time. He was digging through old Chris Stapleton songs and found that song and brought it to me, and it really felt like the graduation from my last record, Black Sheep. It's totally that tortured, bluesy, devil-may-care vibe that I really love to bring to the live performance. It's just such a mood and it makes me want to drink whiskey. It was just very loose and the musicians all together just feeling their way through it.”

All the Cool Girls
“It's like an ode to the girl gangs. It reminded me of going out with a bunch of my girlfriends in my twenties and just being a mess and getting drunk and waking up hung over. It's the timestamp of that era in life.”

The Faker
“I wrote that with Waylon Payne and Hillary Lindsey. Waylon is such a classic Nashville country singer-songwriter. I love how the lyrics are so simply stated, but loose and open to interpretation. We kept it very old-school country. When we cut that song, we wanted it to feel very much like a modern-day Patsy Cline thing. The take that's on the record was the first take. We didn't tweak a thing about it.”

Living the Dream
“That was me trying to figure out what my dreams meant to me, and the different interpretations of what it means when people say ‘living the dream.’ People will say that to me a lot, especially folks back home. They think I'm down here in Nashville, just a big country music superstar living the dream. I think the dream is so much bigger than trying to get your name at the top of the chart or break records and make money. I think it's just getting to be here and getting to live and hurt and feel and love. I think that it's the perfect song to end the record on, and I hope that listeners can hear the thread of me discovering what that meant throughout the entire project.”