Today I'm out in Philly, my fans waitin' for twelve hours
Just to get their dollar signed

from Drake (Ft. Dennis Graham & J. Cole) – Jodeci Freestyle Lyrics on Rap Genius

Meaning

When Drake & J. Cole recorded the song on June 21st, Jermaine was in Philadelphia at the current stop of his Dollar & A Dream Tour.

Since no tickets were sold but the entrance fee was $1, his fans waited for 12 hours straight, to get to the show and to get their dollar autographed.

On a side note, J. Cole has used this returning concept of only having “a dollar and a dream” in several songs throughout his entire career:
Dolla and A Dream
Dolla and a Dream II
Dollar And A Dream III

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