58. Kanye West f/ Kid Cudi "Welcome To Heartbreak" (2008)
Album: 808s & Heartbreak
Producer: Kanye West, Jeff Bhasker, Plain Pat
Label: Roc-A-Fella, Def Jam
808s & Heartbreakis quite possibly the greatest depressing rap album of all time. The tone throughout is somber—death and failed relationships were common themes. It goes without saying Kanye was going through some heavy shit while recording this album.
The best example of Kanye’s inner-psyche, however, has to be “Welcome To Heartbreak.” It’s where Kanye comes to the realization that he’s not like the rest of us. His fame and fortune have put him in a place much different than those he grew up with. While his friends show him pictures of their kids, all Kanye has to offer in return are pictures of his houses. He’s self aware of just how shallow this is. Sure Kanye’s amassed wealth and success but “Welcome To Heartbreak” leads us to believe he still feels hollow inside. And it’s at this point that he realizes things will never, ever return to normal: “Chased the good life my whole life long/Look back on my life and my life gone.”