Songfacts®:

• In this upbeat, fiddle-infused song, Hailey Whitters looks at the good and bad that life has to offer, concluding that she needs it all to fill her cup. "It's a concoction of all of those little things in life that have a way of making my glass feel half-full," she said. "It's been a hopeful reminder throughout the year and just felt like the right note to start 2021 on."
• Little Big Town perform on this track with Whitters and also appear in the video. The group recorded a song Whitters wrote, "Happy People," in 2017.
• Whitters wrote "Fillin' My Cup" song with her fellow Nashville tunesmiths Nicolle Galyon and Hillary Lindsey. Whitters came up with the title, and Galyon had the idea to turn the lyric into a recipe.
  
  After coming to Nashville from Iowa, Whitters worked as a waitress while she made her way into the industry. She first made her mark as a songwriter, with Alan Jackson's "The Older I Get" and Martina McBride's "The Real Thing." In 2020, she released her album The Dream, produced with Jake Gear, just ahead of the pandemic. "Fillin' My Cup" is her first release since that album - Gear returned to produce it with Whitters.
• The music video was directed by Harper Smith and features appearances by Little Big Town and Ketch Secor of Old Crow Medicine Show. In the video, Whitters plays a bride who gets cold feet and makes a run for it.
• This is one of five new tracks on Living the Dream, a deluxe edition of The Dream. The record finds Whitters calling upon some of her closest friends and collaborators who played a part in her moving from fantasizing about "the dream" to actually living it. Whitters explained to Apple Music that Little Big Town were the first artist that ever recorded one of her songs and took it to country radio. The royalties from "Happy People" helped pay for The Dream record.
  
  "So, I'm waiting tables, I'm trying to save my money, get my money together for the making of The Dream, and those royalty checks started coming in from them," Whitters explained. "So they, quite literally, made it possible for me to be able to put out music and put out that record. I mean, hearing them all mic'd up and someone hit 'play' and getting to hear all their voices on it, it was just really cool."