A friend of mine was playing in a bar the other night, a few originals thrown in with a lot of covers.  His band is tight enough that they'll sometimes learn a song onstage and run through it with an audience.  He was playing along and David Wilcox walked in.  Apparently Wilcox asked him to play Downtown Came Uptown (but didn't join in).
 
Is that a cool thing?  Someone asking "hey, i like you - how would you sound doing MY hit?"
Or is it an arrogant thing?  "hey, play my song, I think it's awesome."

First tell me who David Wilcox is and than I will tell you if he was being arrogant.  I've never heard of him, so I'm going with, "yes, an arrogant sob!"

Haha, he was big here.  But I Wiki'd him, and he's Canadian and may not have done anything elsewhere.
 
https://www.youtube.com/watch?v=i2wOYxm9Pho
 

Just a ruse to garner more performance royalties?

That said... I have never met the man so I have no idea what he's like. Since he's a well loved old school Canucker music icon I'm gonna say... probably pretty cool.
 
And his music just friggen' drips "cool" anyway... despite him being a rather unattractive dumpy old Canadian white guy... even in his prime.
 
lol
 
hestillfriggenrulesthoughsoasfarashismusicologicalexperimentationz
 

Beepster
 
And his music just friggen' drips "cool" anyway... despite him being a rather unattractive dumpy old Canadian white guy... even in his prime.
 

I'm thinking that describes most of us on this forum.  Subtracting "Canadian" of course.

Seriously tho guys... check out that Bearcat link.
 
The guy is a maniacal guitar player and has mastered the guit/vocal interplay.
 
As far as modern blues/rock guit heros/influences of mine I'd put Wilcox just behind SRV.
 
He really is a (and again I'll say this in Canadian-ese) FRIGGEN' awesome guitar player.

Ooooh I fergot about this one...
 
Some people call me a Bad Apple...
 
soooooo gooood.
 
:-)

I'm pretty sure if a known musician walked into a bar where I was performing (s)he would would immediately turn and leave.