Bob Dylan (b.1941) and Miles Davis (1926-1991), for better or worse, have always been at least one – and usually three or four – steps ahead of their critics and fans. Never pandering to what’s expected of themselves, they’ve always done what they’ve wanted, endlessly reinventing themselves: both have had at least four musical reincarnations. And kept going when the going has got tough. One uses his voice as a musical instrument (Dylan) and the other uses his instrument (his trumpet) as a voice (Davis).

They both came from middle class families in small towns and escaped to New York (though in this they were not unique). They started playing music young, in small jazz and folk clubs. Miles Davis played in Harlem and the Greenwich coffee houses in the 1950s, where Dylan would play a decade later. Both were iconic and cool beyond belief in the 60s and 70s; both had a difficult 1980s. A recent poll conducted by Music for Grown-Ups of all-time top 10 musicians listed Dylan as number one and Davis as number two.

Other jazz musicians may have been more influential (and better!) – Duke Ellington, Charlie Parker, Louis Armstrong – but the groups Davis put together and the albums he made were the thing. Similarly, Dylan has a knack for putting together a great band (such as The Band and the Rolling Thunder Revue) and making his records treasured items. Davis’ Kind of Blue and Bitches Brew, and Dylan’s Highway 61 Revisited and Blonde on Blonde are four of the most influential and amazing albums you’ll ever hear. They have both made more than 30 studio albums each – all of which are worth listening to.

Detractors say neither can play or sing. David Bowie (though he is a fan) sang on Song for Bob Dylan that Dylan’s voice was like “sand and glue”, and Miles Davis' tone has been described as “a man walking on eggshells”. Their harsh tones can make for difficult listening to outsiders, but once you get them, you’re hooked. Both have also expressed themselves with painting – and taken it pretty seriously, though the results have generally been disappointing.

Both were fond of improvising in the studio and on stage, with band members often struggling to keep up with them – sometimes not knowing what they were meant to be playing. Dylan’s band still does struggle on occasion, judging by the stern looks he was giving them at a recent concert I went to. It’s sometimes seen as if they Davis and Dylan have disdain for their audiences whilst on stage – Davis used to turn his back to his audience; Dylan usually has no interaction at all with them. But they are there just to play the music; all the rest is meaningless.

They possibly met together a few times in the mid-70s and there are rumours they collaborated on some music. I can’t imagine how it would sound – like walking on eggshells whilst eating sand and glue, I guess.