Jack Kerouac began shopping his second novel, ”On the Road”, in 1952, complete with a cover he designed himself. Publisher A.A. Wyn received the sketch with a little note typed at the very top:

Dear Mr. Wyn:

I submit this as my idea of an appealing commercial cover expressive of the book. The cover for ”The Town and the City” was as dull as the title and the photo backflap. Wilbur Pippin’s photo of me is the perfect ”On the Road” one… it will look like the face of the figure below.

J.K.

Wyn rejected both the novel and the cover idea. ”On the Road” finally was published in 1957 and went on to become a bestseller with all manner of covers – save Kerouac’s original idea.

(Source: thedailywhat, via arvage2)