Hailey Whitters, Little Big Town Collaborate on Buoyant New Song ‘Fillin’ My Cup’

Singer-songwriter Hailey Whitters has teamed up with country vocal quartet Little Big Town for the new single and video “Fillin’ My Cup,” the first new music Whitters has released since her 2020 album The Dream.

A fiddle-driven country-rocker with ringing electric guitars and beefy drums, “Fillin’ My Cup” was written by Whitters with Nicolle Galyon and Hillary Lindsey. It’s another tune full of quirky philosophical observations in the vein of her previous standout releases “The Days” and “Janice at the Hotel Bar.” In this case, Whitters gets the sublime harmony of Little Big Town — plus a solo verse from Karen Fairchild — to sing about accepting the sweet, sour, and bitter of a lifetime journey. “One part happy/One part chaos/Whole lot of borrowed/Little bit of paid off,” she sings.

“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,” Whitters says in a release. “It’s a concoction of all of those little things in life that have a way of making my glass feel half-full.”

The video for “Fillin’ My Cup” is also out today. Directed by Harper Smith, the clip features Old Crow Medicine Show leader Ketch Secor playing his fiddle, Little Big Town drinking in lawn chairs, and Whitters as a runaway bride.

Though this is their first recording together, Little Big Town and Whitters have a previous connection. The group recorded Whitters’ song “Happy People” for their 2017 LP The Breaker; she put together her own version for The Dream in 2020.