Lenny Bruce's real legacy: he wasn't funny. Just important. (Culture and Reviews).

As its title makes plain, the interesting new book The Trials of Lenny Bruce: The Fall and Rise of an American Icon (Sourcebooks), by Ronald K.L. Collins and David M. Skover, traces the myriad legal troubles of arguably the most influential comedian of the past 50 years.

But the volume, which also includes a CD of performances, interviews, and commentary narrated by Nat Hentoff, also drives home a point as iconoclastic as the man himself: Lenny Bruce just isn't that funny anymore--if in fact he ever was.

Part of the reason is that the best stand-up is intensely topical, weaving a dense web of brilliant, if necessarily ephemeral, connections to topics of the moment. Part of the reason is that recordings can't do justice to live performances.

Part of the reason is that Bruce's targets--organized religion, politicians, sexual hypocrisy, racism--long ago lost whatever widespread, uncritical support they once might have enjoyed. (To be sure, Bruce himself contributed to this.) Part of the reason is that Bruce's insistence on his didactic function--"I'm a surgeon with a scalpel for false values," he used to say--transformed him into an adults-only version of the tedious magazine Highlights for Children, whose subtitle threatens to deliver "Fun With a Purpose."

Although his mostly baby boomer champions will disagree, it's tempting to say that Bruce was truly funny only twice in his tortured, abbreviated career--and only once intentionally.

The first time came when he appeared at the Village Theater in New York just a few days after john F. Kennedy had been assassinated. As the biographer Albert Goldman told it, "The more sensitive people among the crowd were feeling a cramp in their guts. They were very worried about how Lenny would treat the subject of the assassination. He couldn't avoid the world's biggest topic, and yet it was terrifying to think what might happen if he said something crude or 'sick.'"

Already in the thick of the legal hassles that would plague him unto death, Bruce took the stage and let a long, pregnant silence build. "Poor Vaughn Meader!" he finally said, invoking the name of the impersonator whose First Family LP had set sales records that would eventually be eclipsed by a JFK memorial album.

The second time Bruce was funny? That came in August 1966, when he overdosed on the toilet of his Hollywood Hills home, a syringe still stuck in his arm. It was the perfect black comedy ending to his life, a death that perversely proved the worst accusations of his legal and cultural tormentors. The man who had been dubbed "America's No. 1 Vomic!" by Walter Winchell and the "high priest of sick comedians" by Time had met his maker in signature style.

Yet to say that Lenny Bruce isn't funny anymore is not to suggest he is unimportant. As a pioneer of the free expression that Americans can now take for granted, Bruce went boldly where no man had gone before--or has had to since.

Born in 1925, Bruce started his career in a countrythat not only routinely suppressed skin mags but banned Lady Chatterley's Lover, Lolita, and Howl as indecent. From his first obscenity arrest in San Francisco in 1961 through cases in Los Angeles, Chicago, and New York, Bruce and his attorneys challenged American courts--and American culture--to expand the boundaries of protected speech.

Collins and Skover recount the blow-by-blow of Bruce's travails and legal arguments in copious and compelling detail, largely steering clear of the hagiography that has too often attended Bruce in the past. Still, they don't scant his legacy: "Lenny Bruce...create[d] new free speech zones for Americans. In comedy clubs across the country, the unstated can be stated, the unheard can be voiced, and the unholy can be exposed. What a tribute to unabashed speech freedom."

Bruce's influence, of course, extends far beyond comedy clubs. You can hear it on talk radio and in recorded music, and it's on display all over cable and even network TV.

And on the U.S. Supreme Court. Collins and Skover persuasively suggest Bruce's ghost hovered over the drama surrounding the most recent major effort by government to regulate speech, the Communications Decency Act of 1996.

The CDA, which prohibited the computer transmission of "obscene, indecent, and patently offensive material" to minors, was "Congress's attempt to turn Internet service providers into vice cops," they write.

When the Court unanimously struck down the law's "indecency" and "patently offensive" provisions as overly broad in Reno v. ACLU, it wasn't just a victory for free speech. It was also a First Amendment punch-line inspired by Lenny Bruce.

Nick Gillespie is editor-in-chief of reason.