Kanye West

Examples of Singing: "Heartless," "Runaway," "Love Lockdown"

We've come to learn that Kanye does it all and enjoys pushing boundaries. The rapper made a bold move in 2008 and dedicated his entire 808s & Heartbreak album to singing, and it proved an excellent catalyst for confronting the pain in his life at the moment.

Conclusion: Kanye's singing is heartfelt, but even when he's killing it with the harmonies, there's always the anticipation for him to spaz out on a rap.