Date: November 23, 2008
Music performed: “Heartless”

Kanye’s 2008 American Music Awards performance was in many ways a live version of the “Heartless” videoThe recreated scene has a Harajuku, Tokyo-like vibe, showing bright neon signs on dark spaces. The background signs shine bright with lyrics and the tracklist from 808s and Heartbreak.

Scattered around the stage, three doll-like background dancers in red made minimal movements. West and his label had been hyping up the possible release of a Kanye clothing line for years, and he debuted an outfit from the line, Pastelle, at the performance (the line never actually came to fruition).

It's obvious that this song was emotional to perform for Kanye, and it’s especially apparent when he ends the performance on his knees practically screaming, “How could you be so heartless” in a cracked voice. Regardless, it ended up being a pretty good night for Kanye, because he won favorite rap/hip-hop album for his album Graduation that same night.