8. Drake f/ Trey Songz & Lil Wayne "Successful" (2009)
Album: So Far Gone
Producer: Noah "40" Shebib
Drake raps about success, a lot. But this song, one of the key tracks from So Far Gone, is the ultimate aspirational anthem of Drake's. In a field of rap songs about success—the hustle, the grind, or simply the reality of most rappers' cutting to having it and its perks—it was a moment of weirdly plain and brilliant honesty: I just wanna be, I just wanna be suc-cess-ful.
And there's that first verse, sure as science, about the superficial desire for success and what it brings. But then, the second verse hits, and something changes: Drake is rapping about his mother crying to him about various problems after she tried to run away from then, and how he showed up after at 40's place to record the song you're hearing (in true Drake fashion, with two bottles of Dom), on the verge of breaking down. The song hit new depths in the third verse when you hear Drake's father's voicemail piped over the track. "Wise words from a decent man," Drake raps, hitting a Freudian nerve that hints at everything that will go unspoken about it, a line that says infinite amounts via its own brilliantly limited scope.
When So Far Gone came out, the idea of a rapper detailing a relationship with their parents and success had been colored in broad strokes. And while it isn't his greatest hashtag-rap line, "I'm the one to paint a vivid picture, no HD" was maybe more true than Drake ever could've realized. This isn't just someone pouring their heart out, it was public therapy with a rapper: Intimate, emotional, devastating, and catchy as hell, too. —FK