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An Artist (i.e. a painter) might have to sell his or her tools to sustain their alcohol addiction due to their lack of finances. A pawn shop is a shop where one can sell one’s random possessions with the hope that if one can gain some financial stability they would be able to buy it back. Macklemore is clearly not being literal he merely means that he sold his potential and what makes him who he is as an artist to the alcoholic in him.

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Hes actually saying that he is selling off those things most important to him to pay for his alcoholism. This is a common problem alcoholics have.

I burn Brother Ali and buy 50, what does that say to you? Macklemore – Contradiction

He illegally downloads Brother Ali a underground rapper , but purchases a mainstream famous rapper like 50 Cent — even though this totally contradicts with the fact that he’s an indie artist like Ali too.

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Get back to my car, and I think I'm trippin', yeah Macklemore and Ryan Lewis (Ft. Ben Bridwell of Band of Horses & Macklemore) – Starting Over

what he was hoping wouldn’t happen has happened and Macklemore is emotionally moved afterwards.

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Back of that meeting on the East Side, shakin' tweakin'
Hope that they don't see it, hope that no one is lookin'
That no one recognizes that failure under that hoodie
Just posted in the back with my hands crossed, shook-en
If they call on me I'm passin' it, they talk to me I'm bookin'
Out that door Macklemore and Ryan Lewis (Ft. Ben Bridwell of Band of Horses & Macklemore) – Starting Over

After a relapse he’s at a meeting. Ashamed of his actions, he hopes no fans will recognize him . he’s avoiding any attention trying to stay under the radar.

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If he is invited to talk to the group he will decline, and if someone tries to talk to him he will leave the meeting.

Ben is actually referring to a narcotics anonymous meeting he attended. He is worried that the others at the meeting will recognize that he relapsed and reveal publicly that he relapsed. Therefore, if anyone at the NA meeting calls on him to share, he will just “pass” or leave the meeting.