A quarter-century ago, Lenny Bruce was jailed for using obscene language in his standup act, but in the decades that followed, comedians have built careers around material that is considered taboo in most other mainstream media forms. Richard Pryor and George Carlin, whose “Seven Dirty Words You Can Never Say on Television” spawned a Supreme Court decision regarding the federal government’s regulation of speech on television and radio, helped to open the door for comics to tackle more controversial topics, and performers ranging from Bill Hicks and Andrew Dice Clay to Sarah Silverman and Amy Schumer have all pushed taboo material to their furthest limits.

But subjects once considered untouchable by the mainstream now form the basis for films and television — see “Shameless,” “Nurse Jackie,” “Weeds” and the upcoming “Deuce” for HBO — which begs the question: can comedians still push the envelope on issues of acceptability and good taste in their standup acts, or has their approach been co-opted by other media? We look at six recent specials by some of comedy’s biggest names to see how they employed — or avoided — controversial subject matter in their latest material.

“Louis C.K.: 2017”
In this seventh hour-long special, C.K.’s penchant for mining the absurdity of uncomfortable subject matter reaches its apex when he addresses the very question of existence, and whether it’s worth continuing. “The whole world is made of people who didn’t kill themselves,” he says. “Life can get very sad, but you don’t have to do it … because you can kill yourself.” That existential foundation runs through subsequent riffs on abortion (“I don’t think life is that important”) and love (“Don’t be greedy and expect it to last”). The special underscores C.K.’s ability to pull material considered dark into view, examine its odd mechanics and then deflate the stigma around it through withering honesty.

“Sarah Silverman: A Speck of Dust”
Silverman devotes a sizable portion of her latest special for Netflix to her own real-life brush with death due to an abscessed windpipe. It may have, in part, contributed to the pensive tone of “A Speck of Dust.” The shocking material on which she made her name is still present – bodily functions and fluids are name-checked throughout. But a lengthy story about her new dog, which she considers putting down to avoid future pain over its death, suggests a new direction for her comedy that unites the rawness of the past with a new and fresh sense of introspection.

“The whole world is made of people who didn’t kill themselves. Life can get very sad, but you don’t have to do it … because you can kill yourself .”
Louis C.K.

“Amy Schumer: The Leather Special”
Like Silverman, Schumer has spun taboo into gold through her television series, “Inside Amy Schumer,” books and feature films including “Trainwreck.” She doesn’t stray far in her debut special for Netflix — served up for audiences’ approval are explicit and self-deprecating takes on her appearance, sex life, a bout with food poisoning and her newfound fame. All pack an expected punch, but Schumer finds greater depth — and surprising humor – in issues with more heat than her raunchier fare, such as gun control and conservative fury. Her line about “the same guy who is like, ‘Git out of our country, foreigner!’ is like, ‘But while you’re here, please enjoy our firearms, legally,” reminds viewers of her talent for tapping uncomfortable material for honest laughs.

“The Age of Spin: Dave Chappelle Live at the Hollywood Palladium” and “Deep in the Heart of Texas: Dave Chappelle Live at Austin City Limits”
both Netflix
No subject proved too hands-off for Chappelle to explore — and ignite — in this pair of specials, filmed in 2015 and 2016 and streamed this year on Netflix. His struggle to balance the positive and negative qualities of Bill Cosby and O.J. Simpson (“And as soon as the door closed, we all looked at each other like, That n—- did that
s—.”), head-on collisions with casual racism and anger (“Everybody’s mad about something”) in his home state, even the success of fellow comic Kevin Hart are all dissected in sharp, insightful (and incisive) terms. Some of the hot-button topics land dully — jokes on LGBTQ issues have drawn ire — but when Chappelle turns his fire on societal ills, he provides a masterclass in turning taboo into commentary.

“Jerrod Carmichael: 8”
Carmichael, the eponymous star of NBC’s “The Carmichael Show,” isn’t often mentioned in the same breath as the others, but his ability to uproot the sensitive core of difficult subjects in his comedy, as evidenced by this HBO special, puts him in contention, if not in league, with them. Carmichael opens with a plaintive question — “Are we going to be OK?” — and details the ways we most likely won’t be through the filters of Trump, race and various societal evils. His calm, conversational delivery — even when debating an audience member on animal rights — allows him to broach an array of controversial topics and slyly upend audience expectations by exploring advocacy for some of the least palatable ones.