50. Lupe Fiasco on Kanye West's "Touch the Sky" (2005)
Album: Late Registration
Producer: Just Blaze
Label: Roc-A-Fella, Def Jam
Lupe skates (zing!) onto the third verse of Kanye's Curtis Mayfield remake, apparently determined to throw in as many double entendres and obscure metaphors as possible in keeping with his reputation as an inventive and eclectic lyricist. With everything from fencing references ("En garde, touché"), Thundercats puns ("I'm trying to stop 'lion' like I'm Mumm-Ra"), and Manga name-drops ("Lupe steal like Lupin the 3rd"), Lupe wisely offsets the geek factor by weaving in a gun punchline and a some porn star talk.