"'Its hard not to remember the first time you met Robert, ask anyone who did. I met him in 1940, just a few montsh before France was invaded and just a few months before the Phony War turned real, and at that time in history, I met Robert Johnson. You always want your first meeting with a legend to be so much greater than it actually was, you want it to be big and special and completely as you would imagine meeting a legend would be like, but really, all there was was this: He was looking around in New York for a good drummer to match his guitar, everybody knew he was the best guitarist around, he needed the best drummer, and that was me. Tommy Dorsey, whose orchestra I was actually trying to join at that time, suggested it to me, why don't you go and work with that Robert Johnson, that performer down in the village, the guitarist. The entirity of Harlem knew him, for no reason really, he was just a talented personality, and people remember those. So I decided to look him up, and we met. Really nothing bigger, we just met. Robert asked me to do some songs, drum to his guitar, help him mix his blues with the jazz he heard everyone else doing (he liked Jazz, he liked all music he heard in New York) and help him put together a band, a good band, he'd let me lead it if I wanted to, he just wanted to have some Jazz musicians, I said yes. For no reason I said yes. It was the beginning of a relationship that's lasted (though been interrupted) for 16 years. Rest in peace, Robert.' - Buddy Rich."(8)
May-August 1942: Johnson tours the eastern coast of the United States, to moderate success, enough so for Decca to keep him. He continued to sell records, and he continues to mix styles from his contemporaries and from his youth.
Summer 1942: Excessive recording and performing leads Johnson to develop an addiction to heroin, as well as an already developed alcoholism, the drugs add further finanical strain on the guitarist, driving him into more work.
Autumn 1942: Robert continues develop his own style while constantly changing styles, from October 1942 he abandons guitar completely, if only temporarily, in favor of Jazz. Mutters of his "selling out" begins to be voices.
Early 1943: Robert embraces Free Jazz completely, working with his singing more than ever before, both in studio and live. Ragtime, Broadway, Free Jazz, bebop, blues, swing and folk is all mixed, match, married and thrown together in Robert's drive to find a genre that satisfies him.
Mid 1943: Robert's addiction starts to spiral out of control, Decca demands that he enter hospital for it, and he complies. Three months is spent in hospital, receiving treatment, in August, he is back but drained from the experience. His music takes a darker turn and he picks up his guitar again and starts writing his own songs again.
Late 1943 to June 1944: Robert builds up his orchestra, consisting of a pianist, a string quartet, two saxophonists, one trumpeter, a drummer and himself singing and playing guitar. Missing is a traditional bassist, Robert explained this with "I'm my own bassist." referring to how he could play a bassline on his guitar. The band achieves great success with its mixture of blues, jazz, ragtime, pop and showtune.
I think I'll stop here, for now. So now first I'm gonna explain my interpretation, well if one listens to Robert Johnson, it's very clear that he was a very eclectic musician, who was mixing in styles that sound very unlike Delta blues of the time, that's why it sounds so much like blues rock to us (OK thats because every guitarist past Johnson has been influenced by him), but Robert Johnson was very eclectic and he seemed to like very many different kinds of music, which is why believe that if he lived and reached New York City, he'd somehow incorperated the jazz he saw around him and the showtunes jazz used exstensively and their sound into his own material. I just think he liked to do things in his own way, and that's why I think if he had gone to New York (which is possible, considering the Harlem Renaissance was happening) he could've gone that track, which is what I went with.
1: POD 1, IOTL he drank the poisoned whiskey (or what it was) and died. In this timeline he just starts a fight instead.
2: POD 2, his imprisonment would've lead to natural bitterness, and with the Harlem Renaissance happening, New York would've been a natural place for a young black musician to go to escape it all.
3: Basically he's doing art pop, or Rock n' Roll a decade or so early.
4: I just thought it was funny and very likely that he got the same response from his old fans as Dylan did when he "sold out".
5: Harlem Renaissance, already said all this, that's the background there.
6: This is just natural, lots of drugs going round back then, it was a popular subject for jazz artists for a reason.
7: Real guy.
8: Robert still dies fairly young, but has a broader effect on music that I will go into later.
SO this was all

.