In December 2007, Lupe Fiasco dropped off his sophomore album The Cool, a project that many fans consider to be his magnum opus. And while the entirety is held in high regard, the somewhat titular track "The Coolest" finds Lupe at his artistic peak, weaving together abstract imagery, clever wordplay, and technically sound flows. Conceptual in nature, "The Coolest" is said to follow the character Micheal Young History as he deals with the seductive allure of The Streets, personified as a seemingly all-powerful woman. The track's lyrics could probably be the subject of an Academic analysis, yet Lupe's capable flow keeps it entertaining enough for those unwilling to take a deeper dive.
While his later work proved divisive, The Cool was an undeniable masterclass in lyricism, with Lupe at the top of his game. In many ways, "The Coolest" stands out as one of his integral tracks, and one worth revisiting on this Throwback Thursday. While I was tempted to go with either "Go Go Gadget Flow" or "Put You On Game," there's something about "The Coolest" that's well suited for these winter months.
Quotable Lyrics
And if the rain stops, and everything's dry
She would cry just so I can drink the tears from her eyes
She'd teach me how to fly, even cushion my fall
If my engines ever stall and I plummet from the sky
But she will keep me high, and if I ever die
She would commission monuments on her bosom to him