Supernatural’ was loosely based on Jack Kerouac’s book “On the Road”. For those of you who don’t know, it’s a road trip novel, mainly autobiographical work, written as a stream of consciousness about Kerouac and his friends criss-crossing the country in 1940s.
Two main characters are named Sal and Dean, and even Kripke admitted he named our Sam and Dean after them. Sal Paradise was Kerouac’s alter ego, and Dean Moriarty was named after his friend, Neal Cassady.
So, let’s talk about Dean Moriarty. He is a beloved character, much admired for his carefree attitude and sense of adventure. A fast-talking womanizer and a con-man with classic good looks and tons of charm, with a love for american cars. Dean races from journey to journey and pulls other people along, always on the move. He grew up with an alcoholic, troubled father for whom he searches on many occasions. His various fixations were drugs, booze, women, and finally the search for his father and constant desire for a family life. In fact, he tried to settle down on many occasions, but his restless spirit always pulled him back on the road.
Sounds familiar? Add monsters and demons, and you’ve got yourself a Dean Winchester.
What most people don’t know is that Dean Moriarty (and subsequently Neal Cassady) is bisexual.
There are two versions of the book. The one that was published in 1950s is a censored version of Kerouac’s original manuscript. Since homosexuality was nothing short of a crime in the 50s America, Dean’s bisexuality was only ever hinted at, and of course remained in the subtext. What we got was a character who was constantly picking up women and even got himself married two times. If you read the book closely though, you can see that his character was also constantly flirting with men, crushing on men, etc. There’s even one male character (Carlo Marx) in the book with whom Dean had a confusing relationship dynamic which was never directly explained, but mostly looked like jealousy over Dean’s constant man-whoring and picking up girls.
The original manuscript of “On the Road” was finally published in 00s, without censorship, but with all the sex, drugs and real names, including the sexual relationship between Dean and Carlo (which were finally named after their real life counterparts, Neal Cassady and Alan Ginsberg). Yeah, Dean and Carlo, I don’t even have to try and make it work. :)
Jokes aside, if you google Cassady’s life, you’ll see that he and Ginsberg had a sexual relationship which lasted on and off for the next twenty years, as he traveled cross-country with both Kerouac and Ginsberg on multiple occasions.
In conclusion, it’s perfectly possible and plausible to have a womanizer, manly character in a story and also have him be attracted to men on occasion. And not only possible for purposes of the story and only in fiction, but also realistic, since the character of Dean Moriarty almost autobiographically follows the life of a real person. In my opinion, it would not be in any way insulting to Dean Winchester’s character to make him ‘suddenly’ attracted to men. Real people like him do exist, and I think it was hinted enough in canon that Dean Winchester isn’t as straight as others would think.
And for final thought, if you doubt that Kripke didn’t have this book in mind anymore after he started filming Supernatural, think again. In the finale of season 5, “Swan Song”, Chuck talks about Impala’s first owner, named Sal Moriarty. Another nod to Jack Kerouac’s classic “On the Road”.
— profound—bondage (SOURCE)