SideOneDummy Records started in 1995 when roommates Bill Armstrong and Joe Sib were both looking to start their own separate record labels. Instead, they decided to pool their money together, about $5,000 each, rent a small office space on Melrose Avenue, and Side One Dummy Records was born.

Early releases consisted of compilations featuring punk and ska bands; How To Start A Fight and Steady Sounds from the Underground, a compilation of early recordings from the Swingin’ Utters, More Scared as well as releases from co-founder Joe Sib’s band, 22 Jacks.

In 1998 SideOneDummy teamed up with Kevin Lyman to release an annual compilation CD featuring acts from the Warped Tour. The 2003, 2004, 2005 and 2006 editions have been certified Gold in the US by the RIAA. The 2003 compilation debuted at #21 on the Billboard Top 200 and at #1 on the Billboard independent album chart. The highest chart position for the Warped Tour Compilation series occurred in 2004 when the album debuted at #8 on the Billboard Top 200 and at #1 on the Billboard Independent album chart.

In 1999 the label added three veteran acts to the roster: 7 Seconds, Suicidal Tendencies and Royal Crown Revue.