I fantasize about a second wind
Grow a moustache
Pick up another bad habit and let the games begin

from Macklemore and Ryan Lewis (Ft. Macklemore) – Cowboy Boots Lyrics on Rap Genius

Meaning

When time is spent at the bar, one sits around fantasizing about all the things they could become.. Since so much time is spent drinking and sitting around, one grows a mustache and picks up another bad habit then “lets the games (being the cowboy boots doing lines in the bar/ the chorus) begin.

He’s sitting at the bar thinking about what he has done and what he could do and then he just needs another burst of inspiration and energy which is what a second wind is. He is fantasizing about having a youthful relapse. Start partying, try to relive those days, but he knows he won’t do it.

He’s saying that as he gets older and wiser, there is less chance to make these kinds of mistakes, even if they do make you feel alive. He’s saying he sometimes imagines that he can go back to that way of life, when he was young and could go through phases, like growing a mustache, and making another mistake like getting on cough syrup. He used to make bad decisions, but they made him feel like he was living his life to the fullest. Now he’s older and can’t do these kinds of things. He has to be more responsible.

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