Well, I've never once listened to music to "try to be cool."
I listen to rap because I enjoy it, and I still follow it because I still like it.
Of the "new generation," I like Kendrick & TDE the most, by far, and it's not even a contest.
After that? I listen to some Drake (good but overrated), as well as Big Krit, Asap Rocky, a little Asap Ferg, J. Cole, and Chance's tape was aight. (not on the hype train, but he had some joints)
I don't like Big Sean - in posse cuts, he's fine, but outside of a 16, he's irritating
I hate Chief Keef and all these "thug" Chicago rappers. They might be great being thugs, but they are bad at music.
Nicki Minaj and this whole femme-C movement she inspired sucks pretty hard. I can't listen to Iggy and Twiggy and Zaealia and Izzalea and Angel or whatever they're called.
I still follow the 90's rappers new music, until they fall off...like, I'll check for Ghost still, but not Ice Cube.
Some 90's talent is actually in their prime now, like Killer Mike. Nas just put out a top 5 Nas album last year. And Kanye is obviously great, despite Yeezus being a 3.5 album hipsters think is a 5.