In his interviews Dylan says that he wrote the Lenny Bruce song in about five minutes. Bruce died in 1966, and Dylan wrote the song around the time of the recording of Shot of Love in 1980. Dylan never expressed any interest in Lenny Bruce before or since, and claims he has no idea why he wrote it.
This gives us a real insight into the meaning of Dylan songs, for here, virtually by his own admission, we have a stunningly elegant piece of writing in which the words have no deep meaning, but are part of a contextual whole, equal in many regards to the melody, chords, the piano and the voice.
It works so well because the music manages to be utterly haunting, and so matches the first line (which is the only line those who remember the song actually know)
Lenny Bruce is dead but his ghost lives on and on
After that the words don’t matter too much – what matters here is the total sound. Perform it in any other way, and a lot would be lost.
It just continues – you can put the track on and play it, and it exists there giving you a feeling about the overall sound, without any sense of the words drifting through – at least not until we get to the final line…
Lenny Bruce was bad, he was the brother that you never had.
And that is about it. An opening line and a closing line, a piano and a voice. All making a simple song that is haunting and exquisite. Sometimes things just work.