Here’s a look at seven comedians who’ve turned the air blue — and changed the culture with their frank and funny observations:

Lenny Bruce

Lenny Bruce
A policeman searches comedian Lenny Bruce after Bruce’s arrest for allegedly using obscene language during his act in a North Beach nightclub, the Jazz Workshop in San Francisco, California.
Photo: Getty Images

Labeled a “sick comic” for his brazen remarks, Lenny Bruce’s humor went viral in the counterculture of the late 1950s and '60s. Married to stripper Honey Harlow, he emceed at the clubs she worked at and forged his down and dirty act there. Transforming himself into what biographer Albert Goldman called an “oral jazzman,” Bruce shocked and delighted audiences with lines like “take away the right to say ‘f**k’ and you take away the right to say ‘f**k the government.’”

In 1964, Bruce was arrested on obscenity charges in San Francisco. (Other cities also banned him from performing.) The comedian doubled down, making his legal woes part of his act, and he was convicted of obscenity in New York in 1964. The conviction was overturned, but Bruce, dead at age 40 from a drug overdose, didn’t live to see his vindication, nor the generation of comics, like Joan Rivers, who stormed through the doors he broke down.

READ MORE: Lenny Bruce's Obscenity Trial Challenged First Amendment Rights and Paved the Way for Other Socially Conscious Comedians

George Carlin

George Carlin was once arrested with Bruce, and in his 1972 routine adapted his seven dirty words from nine that landed Bruce in jail on one occasion, omitting “a**” and “b***s.” Carlin himself was arrested for performing “Seven Words You Can Never Say on Television," part of his image-changing Class Clown album, in Milwaukee that year. The uncensored radio broadcast of a variation on the routine in 1973 set in motion a chain of legal challenges that culminated in the 1978 Supreme Court decision FCC v. Pacifica Foundation, which defined the Federal Communications Commission’s power over regulating the broadcasting of indecent material.

But Carlin had by then found his niche on HBO and pay cable, which let him say “p**s,” “s**t,” “t**s,” “c********r,” ‘c**t,” “f**k,” and “m********r,” as much as he liked. “When you’re born, you get a ticket to the freak show. When you’re born in America, you get a front-row seat,” he commented — but he might be pleased to know that in 2012 the Supreme Court ruled that the FCC could no longer impose fines and sanctions on verbal obscenities and indecency.

READ MORE: How George Carlin’s ‘Seven Words’ Changed Legal History

Richard Pryor

Richard Pryor reigns at No. 1 on Comedy Central’s list of all-time greatest stand-up comedians. Watered-down movies and one rough patch after another in his personal life, including near-immolation while freebasing cocaine in a notorious 1980 incident, didn’t dilute the impact made by profanely hilarious albums and concert movies like the Grammy-winning …Is It Something I Said? (1975) and Richard Pryor: Live in Concert (1979), an HBO staple in its era.

Pryor was the maestro of the “n-word,” titling two of his bestselling albums with it, but following an inspirational trip to Africa in 1979, he abandoned its use. “I went to Zimbabwe,” he recalled. “I know how white people feel now — relaxed! Cause when I heard the police car I knew they weren’t coming after me!”

READ MORE: Richard Pryor Risked It All by Walking off Stage in 1967. Then His Star Rose

Wanda Sykes

“Wouldn’t it be wonderful if our p******s were detachable?” muses Wanda Sykes in one of her sexually charged routines. “We could go for a jog late at night and if a man jumped out of the bushes we could say, no, sorry, we left it at home, got nothing on us!” Sykes is a classic foul-mouthed foil for Larry David on Curb Your Enthusiasm, calling him on his BS, but she’s best when she’s keeping it personal, as when she talks about being prepped to host the White House Correspondents’ Dinner (“Did they really think I was gonna say ‘f**k’ to all those ‘f****g dignitaries?”), and discusses her race and her lesbianism. “It’s harder to be gay than Black. I didn’t have to come out Black,” she says in her Emmy-nominated special I’ma Be Me (2009). “I didn’t have to sit my parents down and tell them about my Blackness.”

Sarah Silverman

Don’t be fooled by her Jewish girl-next-door wholesomeness — Sarah Silverman has claws. But she uses them sweetly. Take her scene-stealing punchline in the 2005 documentary about the world’s dirtiest joke, The Aristocrats —i t’s all very matter of fact, as she frames it as autobiography, candidly describes one lewd act after another, and brings TV host Joe Franklin into the telling. (Outraged, he considered filing a defamation suit against her.)

She carried over that same ironic detachment to the potty- and genital-fixated Sarah Silverman Program on Comedy Central, wrote a book about her bedwetting, and in 2008 won an Emmy for an ode to infidelity she penned for then-boyfriend Jimmy Kimmel’s talk show, “I’m F****g Matt Damon.” “I don’t set out to offend or shock, but I also don’t do anything to avoid it,” she says.

Andrew Dice Clay

Stand-ups like Bruce, Carlin, and Pryor used dirty words pointedly, to take on sacred cows like politics, religion, and “proper” American values. Andrew Dice Clay was a shock-for-shock-sake’s kind of guy, who let it hang out so alarmingly in his Madison Square Garden-filling heyday that MTV banned him in 1989 (“Little Bo Peep f****d her sheep” began his “adult nursery rhymes” routine) and Saturday Night Live cast member Nora Dunn and musical guest Sinead O’Connor, appalled by his misogyny, boycotted his 1990 guest-hosting stint. (He cried about the episode on The Arsenio Hall Show that year.)

Clay, who has said he was an actor playing the part of a shock comic, showed impressive dramatic chops opposite Cate Blanchett in Woody Allen’s Blue Jasmine (2013), and revived his crude “Diceman” persona for the show Dice.