I’m going to go the long and winding road to get to this song so please excuse its wordiness.
In January 2014, I wrote an article – Comedy and the Ages. Lenny Bruce, Charles Bukowski and Hunter S Thompson. It led to a brief but constructive discussion about whether ‘comedy’ is only truly savored in the era it was performed. I argued that comedy in general doesn’t seem to age well unless there is a personal connection to the artist and era it was communicated.
For example, Stanley Kubrick’s classic, Dr Strangelove is considered one of the greatest comedies / satires about the cold war, yet if you didn’t live with the threat of nuclear war in the 60s it may be difficult to appreciate its ingenuity.
Lance at Texan Tales countered my point based on his personal experiences:
I ‘discovered’ Lenny Bruce in 2004. I was born in ’57; too young of course to have known anything of Lenny. I disagree with your view that one must live in the era of the comedian. I have found great joy in Lenny. (And also Brother Dave Gardner: Same era) His philosophy and wisdom are timeless. Yes, it does help to know some cultural history, but it is not required, as some things reach across generations very nicely.
Bob Dylan was born 16 years before Lance, and he sung the following about Lenny Bruce’s impact on him:
Lenny Bruce is dead but he didn’t commit any crime
He just had the insight to rip off the lid before its time
I rode with him in a taxi once
Only for a mile and a half, seemed like it took a couple of months
Lenny Bruce moved on and the ones that killed him are gone
They said that he was sick ’cause he didn’t play by the rules
He just showed the wise men of his day to be nothing more than fools
They stamped him and they labeled him like they do with pants and shirts
He fought a war on a battlefield where every victory hurts
Lenny Bruce was bad, he was the brother that you never had
Sometimes Dylan delivers a ‘nasty’ curl ball on his albums such as Lenny Bruce on the Christian record Shot of Love. From conversing with a wide array of Dylan fans, Lenny Bruce seems to conjure contrasting opinions. It’s not dissimilar to what his political curl ball – Neighborhood Bully did on the 1983 Infidels record. That song was from the point of view of someone using sarcasm to defend Israel’s right to exist; the title bemoans Israel’s and the Jewish people’s historic treatment in the popular press.
I happen to like both aforementioned songs for very different reasons; the latter is my preferred of the two in terms of unapologetic listening enjoyment.
Wikipedia states:
The fourth track, “Lenny Bruce”, is about the subversive Jewish comedian of that name. An influential entertainer whose use of provocative language led to a famous obscenity trial, Bruce died of a drug overdose in 1966. Despite the secular tone of the lyrics, the music is “anchored in the resolute cadences of piano gospel”, according to music critic Tim Riley. Often regarded as a bizarre tribute, the song portrays Bruce as some kind of martyr, even though its characterizations of Bruce have been described as peculiar and almost non-descript.
When Dave Herman asked why, after so many years, Dylan chose to write a song about Lenny Bruce (July 2, 1981 interview), he answered, “You know, I have no idea! I wrote that song in five minutes! I found it was a little strange after he died, that people made such a hero out of him. When he was alive he couldn’t even get a break. And certainly now, comedy is rank, dirty and vulgar and very unfunny and stupid, wishy-washy and the whole thing. … But he was doing this same sort of thing many years ago and maybe some people aren’t realizing that there was Lenny Bruce, who did this before and that is what happened to him. So these people can *do* what they’re doing now. I don’t know.”
The first verse might, in fact, be seen to offer a subtle cut to Bruce’s imitators for whom the use of profanity is a cheap “shock” gimmick, while for Bruce it was a strike for free speech: “He was an outlaw, that’s for sure / More of an outlaw than you ever were.”
References:
1. Shot of Love – Wikipedia
“The more I live, the more I learn. The more I learn, the more I realize, the less I know.”- Michel Legrand
Observation Blogger 
Thats interesting about the comedy. I think it depends on if your comedy is topical or about every day events.
I like what I’ve heard about Lenny Bruce…although at the end all he talked about was his bust… but I did like him.
I do like this song of course!
I wrote in that older article that I had a hard time relating to Lenny’s comedy perhaps because it was so topical of that era, unorthodoxed, anti establishment, and centred on the Catholic church. I understood and admired Lenny for having opened the doors for other comedians decades later to get away with far worse (and without threats from the authorities) and his courage and legacy in Comedy. Yeh, I always liked this song too.
Good point….he did open the doors for other comdians like Richard Pryor and others.
As Dylan implied above; Lenny’s comedy seemed more aimed at ‘free speech’, while many others who rode of his coat tails did comedy for shock value and to be vulgar for the sake of it.
Yea I agree with that last sentence. He was super intelligent.
Interesting post Matt. Bob Dylan, this song is very folky! Not bad.
It’s not in the vicinity of Dylan’s best, but when you align it with his retrospective comments, to me at least it makes it kind of special.
I agree! Bob Dylan is making a statement. No better way to do that than to put it in a song!
I’ve noticed Bob’s good at that.