Hail Mary, come with me, feel like Pac when it hits
Hail Mary is also a prayer used by priests when people are confessing.
Macklemore knows that what he does is wrong, so he asks the prayer to follow him, thus giving giving him a kind of “free pass” to do everything he wants.
“Feel like Pac when it hits” — this part of the line is a double entendre, expanding “Hail Mary” references
When the alcohol hits, Mack will feel dead like Pac. This indicates that he’s about to drink a huge amount of liquor, since it’ll render him almost unconscious
When the condemntion hits him, he’ll feel dead like Pac. He’s generally a person who before anything else wants to stay true to himself and to be able to look himself in the eyes, so the realization of his massive alcohol abuse will hit him very hard.
The line compares Macklemore’s “shot in the gut” (i.e. liquor) to Tupac’s literal shot in the gut.
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