Label was founded in late 1999 in NYC, and the first release came out in early 2000. There were 35 releases over the next five years.

The label was inactive from 2006-2007.

Outlaw Recordings HQ were relocated to Nashville, TN and the label was revived in 2008 with OLR-036. There were 15 releases over the next twelve years.

After 20 years and 50 releases it was announced that the final release would be OLR-050 which was released in 2019.