He poured those experiences into a song called Otherside ("I've seen cocaine bring out the demons inside... Friendship cease, no peace in the mind") which was one of the first tracks to bring his progressive, confessional rapping style to the attention of record labels.
The chorus on Otherside was sung by Fences, a fellow Seattle musician who Macklemore describes as being "fucked up in the same way that I'm fucked up".
Fences, aka Christopher Mansfield, is now preparing to release a new solo album, and Macklemore is giving his old friend a leg-up by appearing on the record's first single, Arrows.
And what a song it is. Driving, hook-laden indie-pop with a judicious use of glockenspiel. This could be a massive radio hit.
Bonus content: Here's a brilliantly over-written statement from Fences about this latest collaboration.
"I have known Macklemore for quite some time. A friendship grown in the coffee shops and broken sidewalks of Seattle. We became sounding boards for each other's music and when it made sense we would combine our efforts. I consider him to be a fearless poet and a selfless human. Arrows is the peak of our mountain."Broken sidewalks. Fearless poet. The peak of their mountain.