They sang an arrangement of Hunter Hayes's "I Want Crazy" as their final competitive song, earning the group $100,000 and a recording contract with Sony.

[5] The five founding members were brothers Chris and Adam Rupp, Matt Atwood, Darren Scruggs, and Dan Lemke.

A Texas native, Foust was then pursuing a career as a singer/songwriter of country music and had recently released a solo album, but was not ready to sign on full-time.

[7] In 2012, Austin Brown was working on a Royal Caribbean cruise ship as a featured singer in their production shows.

At the end of 2012 lead singer Matt Atwood and his wife, who had married the previous year, were expecting their first child.

[8] The group, made up of Chris and Adam Rupp, Lundquist, Foust and Brown, competed in and won the fourth season of The Sing-Off, recording their performances in September 2013.

[9] On March 18, 2016, it was announced that, after sixteen years of performing with the group, co-founder Chris Rupp would be leaving to pursue a solo career.

This announcement also included the release date of their next album—Crazy(er) Life, featuring re-recordings of songs from Crazy Life—to be their last album with Brown.

In an interview Brown said this identity is what grabbed the attention of The Sing-Off’s casting director, who said, “You guys really fit something we don’t have.”[8] Home Free has collaborated with many notable artists.

[23] Home Free has collaborated on several occasions with fellow a capella artist Peter Hollens on "19 You + Me" in 2014 and the hymn "Amazing Grace" in 2016.

[24] In 2020, during the COVID-19 pandemic restrictions, Hollens and Home Free collaborated on a cover of the U2 song "I Still Haven't Found What I'm Looking For", incorporating a choir made up of over 200 members of their respective Patreon patrons; each performer or family group recorded their audio and video remotely.

[28][29] Other notable collaborations include Billy Gilman, Texas Hill (Casey James, Adam Wakefield, and formerly Craig Wayne Boyd), Mark Wills, Brooke Eden, Travis Collins, Amy Sheppard, Rachel Wammack, Lisa Cimorelli, Alabama, and Taylor Davis.

In September 2019 they began their Dive Bar Saints World Tour, which was postponed due to the ongoing COVID-19 pandemic.

On October 8, 2020, the band announced an Indiegogo campaign to fund a virtual holiday concert called "Warmest Winter" to coincide with the release of a new CD of the same name.

[32] The pre-filmed concert was streamed from December 2 to 5, 2020, and featured guest appearances by Alabama and The Oak Ridge Boys, among others.