Why we underestimated him: We didn't think that a brash, overconfident hip-hop producer who favored polo shirts and Louis Vuitton backpacks and compared himself to Michael Jackson could actually ever compare to Michael Jackson.
When he proved us wrong: When he released his debut album, The College Dropout, in 2004 and it was immediately hailed as one of the best rap debuts of all time.
Looking back now, it's amazing to think that there were many labels out there who wrote Kanye off. Although his debut is the highest-selling album of his career, every single solo project that Kanye has released since then, including last year's Yeezus, has debuted No. 1 on the Billboard 200 chart. He has sold more than 20 million albums. Kanye has changed the rap game in immeasurable ways and influenced nearly every single rapper out today. And to think, they thought Pink polos would hurt the Roc.