20 Artists to Watch in 2020


Hailey Whitters was closing in on her first decade in Nashville, that mythologized milestone when artists are supposed to finally start reaping the fruits of their labor. But despite 10 years of hard work, the singer-songwriter still hadn’t had her breakout moment and, fed up with pushing the boulder uphill, she took a step back to reassess.

At that moment, the native of Shueyville, Iowa, matured into the artist she was supposed to be: a probing, fearless songwriter who is more concerned with the busted and broken way things are than the pretty and polished way things are painted to be.

Taken as a whole, The Dream is a collection of 12 tracks, all but two — renditions of Chris Stapleton’s “The Devil Always Made Me Think Twice” and Brent Cobb’s “Loose Strings” — written by Hailey and a roster of A-list women collaborators including Lori McKenna, Hillary Lindsey, Nicolle Galyon and Brandy Clark. She sings of getting day drunk to medicate a heartbreak in “Red, Wine & Blue”; taps into an Eighties Jackson Browne vibe on the marvelous “Dream, Girl”; and romanticizes her Midwest upbringing in the swooning “Heartland.” Elsewhere, she inhabits a tough but secretly vulnerable character in “All the Cool Girls”; laments the worst kind of person to date in “The Faker”; and shares second-hand life lessons in the stunning “Janice at the Hotel Bar,” written with McKenna.

“Janice at the Hotel Bar” ties the entire album together, mixing bits of Hailey’s family wisdom (her grandmother was a font of advice, like “Have a glass of red a day”) with the nuggets of the titular Janice (“Vodka over dessert because sugar goes straight to your hips”), a real-life 80-something woman who preached her worldview to a friend of McKenna’s.

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