Bob Becker started Fearless Records when he was selling his friends tacos at their shows. He would also go to record stores and put their records on consignment. The record label name came from Bob not knowing what he was doing at the time and "not being afraid to jump in head first." Fearless Records was officially formed in 1994.
In 2000, Fearless Records released Punk Goes Metal, the first compilation album from the Punk Goes... series. Since then the Punk Goes... series has expanded. It has included seven Punk Goes Pop releases, two Punk Goes Acoustic releases, Punk Goes 80's and 90's, Punk Goes Crunk, Punk Goes Classic Rock, and Punk Goes X which features cover songs that were featured at the 2011 Winter X Games. Punk Goes Pop 5 was released on November 6, 2012. On January 1, 2014, Fearless Records released a video on their page on YouTube announcing bands that will be releasing albums in 2014 and also announced Fearless Records' compilation of Punk Goes 90's 2.
In 2005, Fearless Records released the studio album All That We Needed by Plain White T's, a thirteen-song collection that proved to be a breakthrough for both the label and the Illinois-based band. "Hey There Delilah," a single from that album, reached No. 1 on Billboard Hot 100, became a success for the label and was certified as a multi-platinum single.
On November 8, 2010, Fearless announced the release of a Christmas-themed compilation album, titled 'Tis the Season to Be Fearless. It would feature eight of their signed artists recording original songs. The album was available for pre-ordering on iTunes the same day, and was released on November 22, 2010. three years later, Fearless Records released Punk Goes Christmas featuring original & cover tracks from All Time Low, ISSUES, New Found Glory, and more.
In 2011, Fearless Records released Breathe Carolina's album Hell Is What You Make It. "Blackout," a single from the album, became another success for the label. It debuted at No. 32 on Billboard Hot 100 and was certified as a gold single.
In October 2012, Fearless Records announced that they had launched a sister label called "Old Friends Records," which would sign more indie rock artists including Hellogoodbye. In November 2013, Fearless Records announced a second imprint label called "Outerloop Records," along with their first signing Ice Nine Kills.
The label with a back catalog of about 150 albums was acquired by Concord Bicycle Music in May 2015 for an estimated $10,000,000.