Songfacts®:

• Kelsea Ballerini is nursing heartache from a broken relationship, but she's able to keep going with the help of a bottle of wine.
  
  I won't cry about love gone wrong
  'Cause tears would water down this ruby red I'm sippin' on
  
  "Hole in the Bottle" is Ballerini's first attempt at one of the most classic country genres; the drinking song.
• Ballerini unveiled "Hole in the Bottle" on February 19, 2020, during a showcase at the 2020 Country Radio Seminar in Nashville. "I was like how much longer can I call myself a country artist and not have a drinking song?" she said introducing the tune. "So meet my drinking song."
• Does the title sound familiar to you? You may be thinking of Cannan Smith's 2015 top 30 hit "Hole In A Bottle."
• Hannah Lux Davis directed the music video, which begins in a black-and-white 1920s-style scene with Ballerini dressed in flapper wardrobe finishing her glass of wine. Once the first chorus hits, the clip explodes into a Technicolor drunken daydream featuring a variety of scenes, including a cameo from the singer's dog, Dibs.
• Kelsea Ballerini was pretty much finished with her eponymous album when she came up with this track. The singer explained to Billboard that she was down in Florida and went to dinner with songwriters Jesse Frasure, Hillary Lindsey, Ashley Gorley, and Steph Jones, to celebrate being done with the record. They had a good amount of wine, came back and started writing "Hole In The Bottle" for fun. "It was just this fun, collaborative jam session," she added. "We were totally free to be silly."
  
  The next morning, they all listened to the demo and even though it was a mess, Ballerini recognized its potential. The singer realized she'd never recorded a drinking song before and decided to make it a late addition to her album.
• In a behind the scenes film, Ballerini reveals she drank real wine for most of the takes in the video, which were all shot in one day. Also, the last shot of the day, a dance sequence, was a nod to both Britney Spears and Shania Twain.
  
  "I was a little nervous about dancing, I'm not going to lie," the singer admitted. "But by that point (I) felt so comfortable with Hannah and the incredible dancers, Lauren and Madison, that we all just hyped each other up and went for it."
• On November 13, 2020, Ballerini released a new version of this song with Shania Twain. "She's inspired me in every way and has become a mentor and friend and added some major sass and spice to hole in the bottle the way only Shania could," said Ballerini.