The Portland Music Awards were founded in 2008 by Craig Marquardo. They were designed to bring attention, appreciation and press to the numerous deserving artists and individuals that make up the rich and vibrant Portland music scene.

The first event was held on January 29th, 2008 at the Roseland Theater. The show was hosted by Kelley Day, television anchor from KOIN News 6, and headlined by Everclear frontman Art Alexakis. The show also featured performances by The Dimes, Ohmega Watts, Debra Arlyn, Josh Hodges, Leigh Marble, Drew Shoals, Carlyle, Caleb Klauder, Papa Salty, Soundspell, Gunnar Roads, Key Of Dreams and Uprite Dub Orchestra.

2009 found the event changing venues, and moved to the Crystal Ballroom. Comcast was the title sponsor of the show, which coupled with the taped television broadcast that aired for several months on Comcast OnDemand. The show was also aired live on the radio, on 89.1fm KMHD.

The 2009 show was hosted by Chloe Houser of PDX TV and nationally reknowned comedian Auggie Smith, and headlined by the local super-band, Floater. There were memorable performances by Mel Brown with Ben Darwish, March Fourth Marching Band, Tea For Julie, Debra Arlyn, Keegan Smith, Morgan Grace, Idle Poet, Acoustic Minds, Echo Helstrom, and Buoy LaRue.

The event did have one trademark memorable moment. While on the smaller finger stage about to present a pair of awards, local television and radio host Dave Anderson made the night interesting. He was talking while taking small steps to his right, until finally he disappeared from the stage only to be immediately followed by a loud THUD. That was the sound of Dave and his microphone hitting the floor. He bounced up so quickly, and followed it with a series of hilarious jokes, it left the audience wondering if it was staged. It wasn't. The next morning he was on his ABC affiliate, KATU television show, AM Northwest, complaining about the aches and pains he experienced from the fall. The video of that incident has received more views on YouTube than all of the other clips combined.