"Skeptical About the Enterprise"

I've just run across this quote from Barack Obama on his interaction with Bob Dylan:

“Here’s what I love about Dylan – he was exactly as you’d expect he would be. He wouldn’t come to the rehearsal. He didn’t want to take a picture with me; usually all the talent is dying to take a picture with me and Michelle before the show, but he didn’t show up to that. He played The Times They Are a-Changin’. A beautiful rendition. The guy is so steeped in this stuff he can come up with a new arrangement and the song sounds completely different. Finishes the song, steps off the stage ... comes up, shakes my hand, sort of tips his head, gives me just a little grin and then leaves. That was our only interaction with him. And I thought, That’s how you want Bob Dylan, right? You don’t want him to be cheesin’ and grinnin’ with you. You want him to be a little skeptical about the enterprise.” ~President Barack Obama

What I love in this posture from Dylan is his willingness to engage structures and persons of power but to have the artistic discipline to remain 'a little skeptical about the enterprise'.  It seems this is the type of posture I've been seeking to articulate spiritually when it comes to structures of formal religion. I understand there are sincere actors and that the structures themselves are necessary. But there must also always be an element that retains the spiritual and artistic (or may I be so bold to say - prophetic) discipline to remain skeptical about the enterprise, to not be coopted by that poisonous urge to take the Lord's name in vain for the sake of self-righteous juice. 

https://www.youtube.com/watch?v=k2sYIIjS-cQ