What does this mean in the digital age?  Can it possibly mean anything?  As Blossom Dearie once sang, 'When it was hip to be hep...' etc. 
Travis Bickle in 'Taxi Driver': 'I'm hip...' 
As I was reading recently, any claim to hipness disqualifies you immediately.  The same writers, assessing the counter-culture of the 1960s, proclaimed it as square as the Establishment it was knocking: too self-conscious, too organized.  Too tied up with capitalism (irony of ironies; perhaps).  Woody Allen professed to hate the counter-cultural changes and all that went with them: The Beatles, Dylan, even Elvis Presley.  He stuck close (I'm guessing) to the likes of Bechet and Picou. 
Even Sahl and Bruce needed to make a living.  Kerouac tried to (and generally failed). 
Another question:  What, now, is a 'hipster'?  Just some granola-cruncher with a bushy beard and Red Wings? 
That absurd book, 'The Hip'...  Put Mr. Chet on the cover, then hope and pray...