Hailey Whitters Deluxe Album Living the Dream
Rising Country Artist Hailey Whitters Updates
Iowa-born Hailey Whitters is a rising country artist. Her latest songs from her upcoming album Living The Dream (2021) include “Fillin’ My Cup (feat. Little Big Town) and “Glad To Be Here” Feat. Brent Cobb. Her previous albums include “Black Sheep” (2016) and “The Dream” (2020).
“Glad To Be Here” Feat. Brent Cobb
1/29 New single “Glad To Be Here” (feat. Brent Cobb)”

“Glad To Be Here” Feat. Brent Cobb
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“Fillin’ My Cup (feat. Little Big Town)
1/4 New single “Fillin’ My Cup (feat. Little Big Town).”

The song was written by Whitters, Songs & Daughters’ label head Nicolle Galyon, and Hillary Lindsey and was co-produced by Whitters and Jake Gear.
Hailey Whitters quote about “Fillin’ My Cup”
I wrote this song with Hillary Lindsey and Nicolle Galyon. I’d had the title ‘Fillin’ My Cup’ for a while, but then Nicolle had the brilliant idea to turn the lyric into a recipe. It’s a concoction of all of those little things in life that have a way of making my glass feel half-full. It’s been a hopeful reminder throughout the year and just felt like the right note to start 2021 on.
“Fillin’ My Cup (feat. Little Big Town).”
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Official Video
The director’s cut of the official video also just dropped featuring Whitters, Little Big Town, and Old Crow Medicine Show’s Ketch Secor.
Hailey Whitters quote about her second studio album “The Dream” (2020)
This record was a labor of love for so many of us involved in the making of it, especially in the early days when it was just a handful of waitressing tips and Hail Marys. I’m humbled and proud to see it resonate the way it has. It’s been the best reminder to stay true to who I am as an artist and storyteller.
The Dream
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