It is not quite usual that a novel becomes the symbol of a whole era, and it is even rarer that named novel remains so extremely popular after the official "fall" or passing of the generation it was written for/about.
One Flew Over the Cuckoo's Nest or The Catcher in the Rye might be influential and cultic, but in my humble opinion the two ultimate novels that make the list of masterpieces I have mentioned above are Fear and Loathing in Las Vegas by Hunter S. Thomson and On the Road by Jack Kerouac.
On the Road "celebrates" (if a novel can celebrate... it's author surely can't anyway, unless in Heaven) its 50th anniversary today (September 5) so this is the reason of this post, at least, the main reason.
What makes On the Road unique is its quirky humour, odd acts and weirdly loveable characters. It perfectly represents the Beat Genetation with all its problems. The novel is largely autobiographical hence many things, characters features in it are real, or are inspired by existing persons. I think it is even more fun to read it knowing almost all of it happened and looking up the real people behind the aliases can be really exciting.
Empty Mirror Books has a list of Kerouac's characters, with the real and fictional names. You can check this list by clicking HERE.
So do I have to tell the story? I think you already know all of that. If not, you can guess it by the title: it's the story of Mr. Kerouac's (and his occasional and all-time friends', including Dean Moriarty /Neal Cassady in reality/, who has since become something very much like an icon due to this novel) road trips across mid-century America. If you haven't read it yet, hurry up, I assure you it will be an eternal experience.
There are also legends of how/why/where/when he wrote the book and even the life of Kerouac was interesting, not only because of his inner circle and pals (including many if not all of the greatest names of the generation, from Allen Ginsberg to Ken Kesey) but because of all his wanderings and thoughts. I also like it about him that he changes style when writing - for example, his other novel, The Subterraneans is written in an absoultely different yet overwhelming style, but still, it has the characteristics of Kerouac himself (this novel followed On the Road in 1958).
If you want to see him with someone else's eyes, read the book that was written by his daughter, Jan Kerouac and is basically a reaction to On the Road. It's entitled Baby Driver and though it is called "semi-autobiographical", it is just as interesting to read and it's plain to see there are many autobiographical acts in it, especially when she talks about her relationship with her father.