20.) Drake – “Best I Ever Had”

What I like about Drake is that he’s not a stereotypical rapper from the hood that raps about being a gangster. He grew up in a wealthy household in the suburbs and he doesn’t try to act like he’s anything else. His songs bring a different feel and story to them that are rare to find in rappers today. The truth goes so much further than a lie. “Best I Ever Had”, even now remains on constant repeat.

19) Drake – “Brand New”

The song is jazzy and bluesy and sophisticated and intelligent. Just when you think you know where it’s going it takes you in a completely different direction, much better than the one that you anticipated. If you can get through the whole thing without hitting the “repeat” button, you’re not really listening.

18.) Drake – “Look What You’ve Done”

It’s an incredibly revealing look at the people who helped make Drake the man he is, including references to how his initial communication with Lil Wayne and departure from the world of acting led him to where he is now. Drake has never been this candid about his family before, as he dedicates verses to the inspiring women in his life while recounting his mother’s health struggles and the at times strained relationship he’s had with his father, without seek pity or sympathy from his listener. In fact, though he takes a guilt-free approach to being emotional, he infers that personal obstacles don’t warrant listener coddling, following one revealing line with his own sarcastic, self-mocking aside (“Boo-hoo, sad story. Black American dad story”).

17.) Drake – “Karaoke”

It’s simple and nice, but nothing extraordinary.

16.) Drake – “Club Paradise”

Something about that first verse that just pulls me in!

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