I confess to being a bit of a Dylan obsessive (all the studio albums, all the bootleg series, mono re-issues, hundreds of live recordings…..), but even I would concede that his voice is problematic for some.
That being said, his output is very varied from the early solo acoustic through mid-60s electric, country, gospel etc, and it’s not axiomatic that you will prefer the early stuff over some of his output from the 90s and 00s.
For what it’s worth I would suggest:
– Blonde on Blonde/Highway 61 Revisited
– Blood On The Tracks
– Before The Flood (live in 1974 with the Band; far better than the Budokan live album)
– Street Legal is to me a hugely underrated album from 1978
– The Gospel Years (1979 – 1981) are difficult. The studio albums never quite take off, but the live shows were imho amazing (I saw him at Birmingham NEC). If you can get hold of Toronto 1980, it is superb and needs an official Bootleg Series issue.
– I’m very fond of the 1986 shows with Tom Petty & Amazon are selling the Sydney show (originally a radio broadcast) for £10 which is a bargain.
– After seemingly losing his way between 1985 and 1995 (with the notable exception of Oh Mercy from 1989), Dylan suddenly hit form again with Time Out Of Mind, Love And Theft and (above all to me) Modern Times (which is as good as anything he’s ever released). It’s always fun asking people who wrote Make You Feel My Love, to which most reply “Adele”. But of course it’s Dylan off TooM.
And to be honest, that’s just scratching the surface…..