Songfacts®:

• This song is about the comedian Lenny Bruce, who was famous for his raunchy material that landed him on trial for obscenity charges in the '60s. Dylan explores how Bruce was vilified for his words, when he never committed any real crimes. Bruce died of a drug overdose in 1966 at age 40, and became an icon after his death - a symbol for how a myopic society can destroy an artist before he can be appreciated. Lenny Bruce also gets a mention in the R.E.M. song It's the End of the World As We Know It (And I Feel Fine) and appears on The Beatles Sgt. Pepper album cover.
• Former Wall of Voodoo frontman Stan Ridgway covered this song for his 2010 album Neon Mirage. Ridgway told Songfacts: "It's not so much that Lenny Bruce affected me, although I'm certainly aware of his life and his career and his recordings, and his place in culture. But the song itself is about a lot more than just Lenny Bruce. That's the great thing that Bob did with that song. There's always something deeper than just what's on the surface. There's always some sort of other facets, and once you get to that, you see a reflection into some other place. I look at it as a kind of celebratory tribute to anyone that's laid his body on the barbed wire for a cause or for a perspective or for an idea about what art is or freedom of speech or any of those things."
• In a 1981 interview, London-based journalist Dave Herman asked Dylan why he chose to write a song about Lenny Bruce so long after the comedian's death. Dylan responded that he had "no idea," but he did find himself reflecting on how Bruce had been idolized in retrospect after having been ignored and vilified in his lifetime.
  
  Dylan saw Bruce's influence on the comedy of the '80s, which he called "rank and dirty and vulgar and very unfunny and stupid and wishy-washy and the whole thing." He seemed to be saying that the new comedians had kept the vulgarity while forgetting the philosophical depth of Bruce, but before he could complete his thought, Herman steered the conversation towards Bruce's views of organized religion (this was during Dylan's most intense Christian period.)
• The musicians on "Lenny Bruce" are:
  
  Steve Ripley: guitar
  Fred Tackett: guitar
  Carl Pickhardt: keyboards
  Benmont Tench: keyboards
  Stephen Eric Hague: keyboards
  Tim Drummond: bass
  Steve Douglas: saxophone
  David Campbell: viola
  Dennis Karmazyn: cello
  Madelyn Quebec: background vocals
  Regina McCrary: background vocals
  Clydie King: background vocals
• Guitarist Danny Kortchmar also took part in the Shot of Love album sessions and was present during early rehearsals when Dylan first introduced the song. Benmont Tench was at those rehearsals, too.
  
  "We're standing around by the piano, waiting for Bob to show up, then he finally walks in and goes, 'I wrote this tune last night, sits down at the piano and plays Lenny Bruce for us," Kortchmar recalled to Uncut magazine. "It was amazing! Benmont and I just looked at each other like, 'Wow!'"