Ginsberg's willingness to talk about taboo subjects made him a controversial figure during the conservative 1950s, and a significant figure in the 1960s. In the mid-1950s, no reputable publishing company would even consider publishing Howl. At the time, such "sex talk" employed in Howl was considered by some to be vulgar or even a form of pornography, and could be prosecuted under law. Ginsberg used phrases such as "cocksucker", "fucked in the ass", and "cunt" as part of the poem's depiction of different aspects of American culture. Numerous books that discussed sex were banned at the time, including Lady Chatterley's Lover. The sex that Ginsberg described did not portray the sex between heterosexual married couples, or even longtime lovers. Instead, Ginsberg portrayed casual sex. For example, in Howl, Ginsberg praises the man "who sweetened the snatches of a million girls". Ginsberg used gritty descriptions and explicit sexual language, pointing out the man "who lounged hungry and lonesome through Houston seeking jazz or sex or soup." In his poetry, Ginsberg also discussed the then-taboo topic of homosexuality. The explicit sexual language that filled Howl eventually led to an important trial on First Amendment issues. Ginsberg's publisher was brought up on charges for publishing pornography, and the outcome led to a judge going on record dismissing charges, because the poem carried "redeeming social importance", thus setting an important legal precedent. Ginsberg continued to broach controversial subjects throughout the 1970s, 1980s, and 1990s. From 1970 to 1996, Ginsberg had a long-term affiliation with PEN American Center with efforts to defend free expression. When explaining how he approached controversial topics, he often pointed to Herbert Huncke: he said that when he first got to know Huncke in the 1940s, Ginsberg saw that he was sick from his heroin addiction, but at the time heroin was a taboo subject and Huncke was left with nowhere to go for help.
Role in Vietnam War protests
Ginsberg was a signer of the anti-war manifesto "A Call to Resist Illegitimate Authority", circulated among draft resistors in 1967 by members of the radical intellectual collective RESIST. Other signers and RESIST members included Mitchell Goodman, Henry Braun, Denise Levertov, Noam Chomsky, William Sloane Coffin, Dwight Macdonald, Robert Lowell, and Norman Mailer. In 1968, Ginsberg signed the "Writers and Editors War Tax Protest" pledge, vowing to refuse tax payments in protest against the Vietnam War, and later became a sponsor of the War Tax Resistance project, which practiced and advocated tax resistance as a form of anti-war protest.
He was present the night of the Tompkins Square Park riot (1988) and provided an eyewitness account to The New York Times.
Relationship to communism
Ginsberg talked openly about his connections with communism and his admiration for past communist heroes and the labor movement at a time when the Red Scare and McCarthyism were still raging. He admired Fidel Castro and many other Marxist figures from the 20th century. In "America" (1956), Ginsberg writes: "America, I used to be a communist when I was a kid I'm not sorry". Biographer Jonah Raskin has claimed that, despite his often stark opposition to communist orthodoxy, Ginsberg held "his own idiosyncratic version of communism". On the other hand, when Donald Manes, a New York City politician, publicly accused Ginsberg of being a member of the Communist Party, Ginsberg objected: "I am not, as a matter of fact, a member of the Communist party, nor am I dedicated to the overthrow of the U.S. government or any government by violence ... I must say that I see little difference between the armed and violent governments both Communist and Capitalist that I have observed".
Ginsberg travelled to several communist countries to promote free speech. He claimed that communist countries, such as China, welcomed him because they thought he was an enemy of capitalism, but often turned against him when they saw him as a troublemaker. For example, in 1965 Ginsberg was deported from Cuba for publicly protesting the persecution of homosexuals. The Cubans sent him to Czechoslovakia, where one week after being named the Král majálesu ("King of May", a students' festivity, celebrating spring and student life), Ginsberg was arrested for alleged drug use and public drunkenness, and the security agency StB confiscated several of his writings, which they considered to be lewd and morally dangerous. Ginsberg was then deported from Czechoslovakia on May 7, 1965, by order of the StB. Václav Havel points to Ginsberg as an important inspiration.
One contribution that is often considered his most significant and most controversial was his openness about homosexuality. Ginsberg was an early proponent of freedom for gay people. In 1943, he discovered within himself "mountains of homosexuality." He expressed this desire openly and graphically in his poetry. He also struck a note for gay marriage by listing Peter Orlovsky, his lifelong companion, as his spouse in his Who's Who entry. Subsequent gay writers saw his frank talk about homosexuality as an opening to speak more openly and honestly about something often before only hinted at or spoken of in metaphor.
In writing about sexuality in graphic detail and in his frequent use of language seen as indecent, he challenged—and ultimately changed—obscenity laws. He was a staunch supporter of others whose expression challenged obscenity laws (William S. Burroughs and Lenny Bruce, for example).
Association with NAMBLA
Ginsberg was a supporter and member of the North American Man/Boy Love Association (NAMBLA), a pedophilia and pederasty advocacy organization in the United States that works to abolish age of consent laws and legalize sexual relations between adults and children. Saying that he joined the organization "in defense of free speech", Ginsberg stated: "Attacks on NAMBLA stink of politics, witchhunting for profit, humorlessness, vanity, anger and ignorance ... I'm a member of NAMBLA because I love boys too—everybody does, who has a little humanity". In 1994, Ginsberg appeared in a documentary on NAMBLA called Chicken Hawk: Men Who Love Boys (playing on the gay male slang term "Chickenhawk"), in which he read a "graphic ode to youth".
In her 2002 book Heartbreak, Andrea Dworkin claimed Ginsberg had ulterior motives for allying with NAMBLA:
[I]n 1982, newspapers reported in huge headlines that the Supreme Court had ruled child pornography illegal. I was thrilled. I knew Allen would not be. I did think he was a civil libertarian. But, in fact, he was a pedophile. He did not belong to the North American Man/Boy Love Association out of some mad, abstract conviction that its voice had to be heard. He meant it. I take this from what Allen said directly to me, not from some inference I made. He was exceptionally aggressive about his right to fuck children and his constant pursuit of underage boys.
Demystification of drugs
Ginsberg talked often about drug use. He organized the New York City chapter of LeMar (Legalize Marijuana). Throughout the 1960s he took an active role in the demystification of LSD, and, with Timothy Leary, worked to promote its common use. He remained for many decades an advocate of marijuana legalization, and, at the same time, warned his audiences against the hazards of tobacco in his Put Down Your Cigarette Rag (Don't Smoke): "Don't Smoke Don't Smoke Nicotine Nicotine No / No don't smoke the official Dope Smoke Dope Dope."
CIA drug trafficking
Ginsberg worked closely with Alfred W. McCoy on the latter's book The Politics of Heroin in Southeast Asia, which claimed that the CIA was knowingly involved in the production of heroin in the Golden Triangle of Burma, Thailand, and Laos. In addition to working with McCoy, Ginsberg personally confronted Richard Helms, the director of the CIA in the 1970s, about the matter, but Helms denied that the CIA had anything to do with selling illegal drugs. Allen wrote many essays and articles, researching and compiling evidence of the CIA's alleged involvement in drug trafficking, but it took ten years, and the publication of McCoy's book in 1972, before anyone took him seriously. In 1978 Ginsberg received a note from the chief editor of The New York Times, apologizing for not having taken his allegations seriously. The political subject is dealt with in his song/poem "CIA Dope calypso". The United States Department of State responded to McCoy's initial allegations stating that they were "unable to find any evidence to substantiate them, much less proof." Subsequent investigations by the Inspector General of the CIA, United States House Committee on Foreign Affairs, and United States Senate Select Committee to Study Governmental Operations with Respect to Intelligence Activities, a.k.a. the Church Committee, also found the charges to be unsubstantiated.