From O's to opposite of Orphan Annie
from Jay-Z – Dirt Off Your Shoulder Lyrics on Rap Genius
Meaning
More alliteration! He went from selling Ounces of marijuana to being the Opposite of Orphan Annie (she was broke; he’s rich)

Also, notice the “O’s” in Orphan Annie’s eyes (she had her eyes spooned out at a young age..)
More seriously, Jay’s first mega-hit, “Hard Knock Life (Ghetto Anthem)” sampled a song from the musical Annie
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