Fearless is based in Culver City, California, and is best known for its early pop punk moments captured in the Fearless Flush Sampler and Punk Bites releases, as well as additional releases by bands such as Bigwig and Dynamite Boy; and later Sugarcult; Plain White T's; The Aquabats; Amely; and post-hardcore releases by At the Drive-In and Anatomy of a Ghost.

Acts such as Blessthefall, Bloodywood, The Word Alive, Ice Nine Kills, Mayday Parade, Pierce The Veil, Starset, The Pretty Reckless, Underoath and The Color Morale have showcased post-hardcore, metalcore, hard rock and alternative rock bands that have emerged in recent years.

The record label name came from Becker not knowing what he was doing at the time and "not being afraid to jump in head first.

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.

[5] Three years later, Fearless Records released Punk Goes Christmas featuring original & cover tracks from All Time Low, Issues, New Found Glory, and more.