I read a very good comment on Reddit about it I agree with:
Kanye picked out some controversial famous people that he's either worked with or have been associated with in the past. He picked out a wide spectrum of people, probably because there's no person who likes everyone in the video. The video itself is really uncomfortable, because it mirrors how the media/world is super obsessed with these famous people, almost in a serial killer kind of way. Even when these famous people are really vulnerable (sleeping and naked), we still keep looking at them. At the end though, he thanks them for being famous and kind of having to put up with being famous. There's a redeeming/clear shot at the end of the whole painting. Reminds me that these people have still put in a lot of work and that there are people who look up to them nonetheless, and how everything might look good on the outside, but we don't have a clear picture of how it actually is. Kanye breaks the 4th wall at the end by looking at the screen, kind of saying "I know".
Of course who wouldn't want to do that..(maybe those that were born that year would not be able to play samp because they were either just born or are 5 years old)
Bob is walking on the road with a doctor.
Bob is the doctors son,
But the doctor is not the boy's father.
How is this possible ?