Well in retrospect you have a mighty fine point.
He's trying to stay "hip" and not doing a terribly great job.
Then again he might even be proud of the success he's had, Supernatural revived his career so to speak, sold 25 million copies and won over a billion kazillion grammys. I don't think it's keeping him up at night thinking "god what have I done?".
On the up side it did expose him to a lot of younger people who then got to learn about the great stuff he was doing in the 60s and 70s.
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