One thing we can say with certainty: Obama is the only living former president who would have this much hip hop, rap, and music by POC on his radar. I guarantee you that both Bushes, Clinton, and Carter haven't even heard of half the people on this list, let alone listened to these songs. If they did, it's doubtful they'd be able to connect with them. That is another thing about him that makes Obama feel like ours; like someone who understands our generation, our values, and our way of speaking. Music is a great connector, not appreciating the poetry of Kendrick (or Chance, or Rihanna) is one of those things about the current administration that makes them feel even further away from where we are. Music is a language that matters, and Obama's playlist hammers that point home for everyone who looked at it and thought, That's my president.