In 2014, Kane Brown began posting videos of his covers of songs by Brantley Gilbert, Billy Currington, Alan Jackson, and other singers on social media. He acquired a following for his homemade videos on Facebook. His cover of Lee Brice’s “I Don’t Dance” was one early video that gained wide attention. Released on September 30, 2015, his cover of George Strait’s “Check Yes or No” went viral and received more than seven million views. His number of followers on Facebook quickly reached more than a million, leading to a teaser clip for his own single “Used to Love You Sober” hitting one million views in less than three hours upon its release on October 8, 2015, and then reaching more than 11 million views in two weeks.
Brown was initially signed to Zone 4 with Jay Frank as his first manager. Martha Earls became his manager in 2016.
In 2014, Brown raised funds via crowdfunding site Kickstarter to produce a six-song EP, which he recorded in Nashville at the home studio of Noah Henson, guitarist for Brantley Gilbert. The EP, titled Closer, was released on June 2, 2015, and debuted on the Top Country Albums chart at number 22, selling 3,200 copies in its debut week. A single from the EP, “Don’t Go City on Me”, was first released on October 22, 2014, and reached number 43 on the Country Digital Songs chart.
Brown released a new single “Used to Love You Sober” on his birthday (October 21) in 2015, and the song was spotlighted on Zane Lowe’s Beats 1. It reached number two on the Country Digital Songs chart based on just two days of sales, with 38,000 copies sold. The release of the single also pushed his EP Closer up the chart to number 22 on the Top Album Sales chart. A second song, “Last Minute Late Night”, was released on November 4, 2015, and debuted on the Country Digital Songs chart at number nine, with 26,000 copies sold. Another single, “I Love That I Hate You”, followed three weeks later on November 30, 2015, and sold 17,000 copies in the first week.