23. Drake "Brand New" (2008)

Complex says: On this So Far Gone EP bonus track, Drake's wondering whether his love interest has already experienced all the things he's doing for her. The layered harmonies on the hook really show off Drake's versatility as a vocalist, making for a flawless ballad. But since it was leaked nearly a year before appearing on the EP, it probably wasn't brand new to her. Sorry to break it to you, B.