For me personally, to win a Golden Globe... would likely be the pinnacle of my career.
That said, in the bigger picture of art you have to differentiate between "Pop Art" (I.e. what your peers think is important right now) and "Great Art."
Even if Husker says he doesn't like KK, he obviously knows who he is and could name some of his songs. So I think we all agree that he's achieved Pop Art Fame. Yet that says nothing about if KK is worthy of Great Art Fame; where people will still know his name in 500 years like Homer or Shakespeare. And none of us in here reading this are going to live long enough to see that question answered.
But to be honest, on the Great Art question I'm probably with Husker with regard to Kristofferson and doubt his work will stand the test of time and anyone who doesn't get it is a dope. He's written some great songs and seems like a person other people like being around. But he's far from the end all be all.