User macdaddyj pointed out an interesting play on words in the title of this track, “A Wake”.

Throughout the song, Macklemore emphasizes his spiritual “awakening” after a difficult time with drugs and alcohol in his own life. Now that he is “awake” to his own and others' foolishness, he is ending his old ways and finally putting his old life to death. This song represents the mourning of his past life, or in other words, a “wake”