61. Estelle f/ Kanye West "American Boy" (2008)
Setting out to break his new artist, Estelle, in 2004, John Legend was hit with the biggest alley-oop ever when Kanye decided to jump on her single “American Boy.” He contributed not one but two verses—a big look from one of the most popular rappers in history.
The will.i.am backdrop gave Yeezy a smooth and airy canvas, on which he stunted about being an international playboy, and selling out floor seats across the globe. The chemistry between Ye and Estelle was evident, making this her biggest single to date.