I saw the Nightline interview and West did, in fact, drop the ball. I’m a fan, mind you. But he made the classic mistake christians make with the media of making long and complicated points that were then chopped, pulled out of context and generally used to make him look like an idiot.
West is RIGHT about Hefner in context. GK Chesterton said it best when he said (paraphrase) “Reformers are usually right about what is wrong, but almost always wrong about what is right.” That describes Hugh Hefner precisely. He got popular because he accurately exploited the genuine unhealthy sexual attitudes and beliefs common in America ("sex is a necessary evil - type of attitude). Hefner then used the natural human repugnance to such error, combined it with fallen human concupisence and POOF, you get Playboy.
But West should have seen Nightline coming a mile away. That kind of line works well in a 2 hour seminar when you have people’s full attention. It does NOT work well when you will NOT have control over the edits that take place before broadcasting. Hopefully, he learns from the experience and does better next time.