Hear Hailey Whitters’ ‘Fillin’ My Cup’ Featuring Little Big Town

Hailey Whitters kicks off 2021 with a bang, enlisting Little Big Town to help her sing “Fillin’ My Cup.” Accompanied by a music video starring Whitters as a runaway bride, the new tune adorned with Little Big Town’s big harmonies puts Whitters’ endearing talent front and center.

Directed by Harper Smith, the clip has Little Big Town’s Karen Fairchild, Kimberly Schlapman, Phillip Sweet and Jimi Westbrook looking on as Whitters cinematically flees a small-town wedding. It also features Old Crow Medicine Show’s Ketch Secor playing fiddle, as Rolling Stone points out.

The song itself is Whitters’ first new material since her most recent studio album, 2020’s The Dream. And it does much to show the country singer’s ever-growing strength as both a performer and songwriter.

“I wrote this song with Hillary Lindsey and Nicolle Galyon,” Whitters explains. “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.”

Released on Monday (Jan. 4), “Fillin’ My Cup” technically isn’t the first time Whitters and Little Big Town have tangoed. Whitters co-wrote “Happy People,” the opening track on Little Big Town’s 2017 effort, The Breaker, and last year, Whitters recorded a version of the song herself.

Her rendition ended up on the aforementioned The Dream, Whitters’ breakout album released early in 2020. The set also spawned the single “The Days,” introduced the singer to scores of new fans and helped establish her as a force to be reckoned with in country music.

“All of the praise for The Dream has me quite choked up,” Whitters adds, saying the album 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.”