Why he won

Same here.
The guy seems to never really have been all that comfortable with being "Bob Dylan" until he hit his 60s-70s and realized that he didn't have to take it all that seriously even if lots of other people did. Before that, he just took out all his shit on other people.

Now Leonard Cohen seems to have been bro-tier from the start. Would have loved to hang with him back when he was chilling in Greece back in the 60s.

The guilty undertaker sighs
The lonesome organ grinder cries
The silver saxophones say I should refuse you
The cracked bells and washed-out horns
Blow into my face with scorn
But it's not that way
I wasn't born to lose you

Not a big Dylan fan, he can hit some good places.
From Love Minus Zero:
My love, she speaks like silence
Without ideals or violence.
She doesn't have to say she's faithful
Yet she's true, like ice, like fire.
People carry roses
And make promises by the hours
My love laughs like the flowers
Valentines can't buy her.

In the dime stores and bus stations
People talk of situations
Read books, repeat quotations
Draw conclusions on the wall.
Some speak of the future
My love, she speaks softly
She knows there's no success like failure
And that failure's no success at all.