Oh, Dean, where do we start? To Sal you are "angel" and "devil," "Shrouded Traveler," "Holy Goof," "saint," "God," "Angel of Terror," "Soul of Beat," "con-man," and countless others. You are somehow both a pedophile and sexual icon, hero and potential drug addict, criminal and holy guru. Men want to be you, women want to sleep with you.
As you might have noticed in Sal’s "Character Analysis," Dean features prominently as a hero. An incredibly flawed hero who tends to abandon those who love him and feel no remorse whatsoever at his poor judgment and horribly timed actions. But a hero nonetheless.
Part of why we don’t hate Dean for his actions is that we feel sorry for him. Dean’s a mess. He doesn’t recognize that he’s a mess, and that makes him even more of a mess. He’s running around from one city to the next, one woman to the next, one car to the next, wrecking most of these on the way and feeling the need to move again once he gets to wherever he thought he wanted to be. That qualifies as a mess, as far we we’re concerned.
Dean gets a lot of flack for being attracted to pre-pubescent girls. Along with pubescent girls, older teenagers, and women his own age. Sal makes excuses for this, blaming Dean's time in jail for his sexual depravity. Dean's interest in young girls might even be the result of misplaced love for youth (see "Symbols, Imagery, Allegory" for more on this topic). But no matter what the cause, this attraction features prominently as a main facet of Dean’s madness.
However, Dean's madness isn’t limited to lusting after young girls – it finds its way into all his relationships with women. Dean’s Beat restlessness extends into his love life. Unable to settle on one woman, Dean tries to have all of these women at the same time. What’s even crazier is that most of the women comply. And when that isn’t enough, he even tries to get Sal to have sex with Marylou while he watches. Dean’s insatiable sexual appetite is just one example of Beat Generation dissatisfaction.
The only place Dean holds back sexually is when it comes to gay men; perhaps because Carlo’s advances on Dean are implicit, Dean never directly has to reject him in the text. But he doesn’t encourage Carlo, either. When Dean does seem willing to have anal sex with a man, Sal explains that he does so only for money. What is clear is that for Dean, sex can be the manifestation of a mad desire – or simply a business arrangement.
Dean Moriarty. Let’s see: Professor Moriarty was Sherlock Holmes’ nemesis. An enemy’s name is an interesting choice for Sal's hero, which means there may be something dark about Dean. Flags go up when Sal identifies Dean as the Shrouded Traveler that pursues him ceaselessly across the continent.
Then there’s his fist name: Dean. On the Road was written in the 1950s, right around the time James Dean was a sexy, rebellious icon. He died in a car crash in 1955, two years before the book was published. Plus the character that Dean is based on, Neal Cassady (check out "Brain Snacks"), was an auto thief. Oooh, this is fun.
Dean has this thing about time. He’s either talking about it, or trying to know it, or finding people that do know it. What does "knowing time" mean exactly? In a very literal sense, Dean uses it to talk about musicians. If they can keep a beat, they know time. They are also, apparently, God. Dean says of both Slim Gaillard and George Shearing that they know time and that they are God. Why are the two related? Well you might have to look at what "knowing time" means in a slightly different way.
At a very simple level, sure, "knowing time" can refer to music. But Dean isn’t blowing a horn when he says he knows time. He’s trying to manage his own time, his own life, and his own frantic concern with the passing of time. This concern and understanding of time evolves along with his madness, and we were most interested when Dean shows up in Denver with a pocket watch permanently affixed to his outfit. He switches outfits, so he has to switch the watch. He can’t be without it. When he arrives in Mexico, he trades the watch for a rock crystal. Doesn't he need it anymore? Did he find something in Mexico that’s more important than his obsession with time?
What’s interesting, if you’re into this sort of thing, is to look at Dean’s progression throughout the story. He starts off a little crazy, but nothing that we (or, more importantly, Sal) can’t handle. Sal even says that they "understood each other on other levels of madness."
Then we get to the frantic Dean-madness. Dean feels the need to talk – all the time – at people and without much allowance for listening to the other person's response. This is where the motion business kicks in a little more – he’s got to go, go, go. Sal recognizes this change, and all of Dean’s changes, which tends to happen when you place your idol under obsessively intense scrutiny.
Next we’re at "mysticism" Dean, which is a deceptive stage of his madness that may appear at first glance to be normal. Do not be fooled – objects in text are madder than they appear. Dean is quieter and more inclined to listen, absorbing from the world instead of outputting at a dizzying rate. Where does the madness factor in? There’s a lot of talk about time and God, and this mysterious IT business surfaces (check out "Symbols, Imagery, Allegory" for more on IT). Dean is in his own world.
Next we arrive at The Shrouded Traveler stage. Sal identifies Dean as the mad force that follows him across the country. Then he describes him as a full-blown angel. Dean has come down off his saintly cloud and had his nose in it on the ground. Everything about him has become visceral and physical, from his sexual lust to his mad driving to his physical actions (his belly-rubbing and lip-licking). Dean is hungry for the world, and he’s not waiting for everyone at the table to be served before he digs in. This hunger drives him down into Mexico and back up to New York. He’s hitting a full ten on the scale.
Dean is legitimately off the charts by the end of the book. He has trouble finishing sentences. He mysteriously appears in New York and then rapidly leaves again. He can’t explain himself and mutters on about time. Did he fulfill Bull’s prophecy of full-blown psychosis "with a dash of violence"? Maybe.