According to Rolling Stone, the winter of 1961 was New York’s coldest winter in 28 years. The cold was the first thing Dylan noticed about the city as soon as he stepped out of his car, but Minnesota is also known for its brutal winters so the cold didn’t come as much of a shock.

I slammed the door shut behind me, waved good-bye, stepped out onto the hard snow. The biting wind hit me in the face. At last I was here, in New York City… The cold was brutal and every artery of the city was snowpacked, but I’d started out from the Frostbitten North Country.

via Chronicles: Volume 1

The “great man” is one of Dylan’s early idols, Woody Guthrie. In “Pretty Boy Floyd”, Guthrie wrote

Yes, as through this world I’ve wandered
I’ve seen lots of funny men
Some will rob you with a six-gun
And some with a fountain pen

“Pretty Boy Floyd” is set during the Great Depression. Its protagonist is a Robin Hood-esque outlaw. One of Floyd’s great deeds was paying off the mortgage of a starving farmer’s home after a greedy banker roped the farmer into a mortgage he couldn’t afford. Dylan saw that same type of greed in the housing market of 1960s New York.

After performing with Neil for a while (“weeks and weeks” may be an embellishment), Manny Roth, the owner of Cafe Wha?, offered Dylan a regular shift as a harmonica player in the afternoons. This was Dylan’s first consistent gig in New York.

The man who loved Dylan’s sound was Fred Neil, MC of Cafe Wha? in Greenwich Village. As Dylan wrote in 2004’s Chronicles: Volume 1,

“[Neil] asked me what I did and I told him I sang, played guitar and harmonica. He asked me to play something. After about a minute, he said I could play harmonica with him during his sets. I was ecstatic. At least it was a place to stay out of the cold. This was good.”

If the account Dylan gave to biographer Robert Shelton is to be believed, the “rocking, reeling, rolling ride” subway ride is likely a metaphor for the dangerous months spent after he got out of the car on 42nd Street and before he arrived in Greenwich Village.

We hustled for two months. Sometimes we would make $150 or $250 a night between us, and hang around in cars. Cats would pick us up and chicks would pick us up. And we would do anything they wanted, as long as it paid. It was very cutthroat…I almost got killed."

Rolling Stone calls this “one of the most fantastical lies [Dylan] ever told”, and says that Dylan immediately travelled to Greenwich Village once he arrived in New York.

Great Danes are the tallest breed of dogs on average, and the tallest dog of all time, Zeus, was a Great Dane. If his stack of money is taller than a GD, then he’s pretty rich.