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Paul Robert Cohen wore a jacket that said "Fuck the Draft" into a courthouse. The Supreme Court ruled it was protected speech under the First and Fourteenth Amendments.

“One man's vulgarity is another's lyric.”— Justice John Marshall Harlan II

The government tried to deny a trademark for "The Slants" as offensive. The Supreme Court struck down the restriction, ruling that the government cannot suppress speech it finds distasteful.

“Speech may not be banned on the ground that it expresses ideas that offend.”— Justice Samuel Alito

Erik Brunetti tried to trademark "FUCT" for his clothing brand. The PTO refused. The Supreme Court ruled 6-3 that the ban on "immoral or scandalous" trademarks violated the First Amendment.

“There are a great many immoral and scandalous ideas in the world, and the Lanham Act covers them all.”— Justice Elena Kagan

Westboro Baptist Church protested a military funeral with deeply offensive signs. The Supreme Court ruled 8-1 that even the most outrageous speech on public issues is protected.

“Speech is powerful. It can stir people to action, move them to tears of both joy and sorrow, and — as it did here — inflict great pain. On the facts before us, we cannot react to that pain by punishing the speaker.”— Chief Justice John Roberts

Larry Flynt published a crude parody of Jerry Falwell. The Court unanimously held that public figures cannot recover damages for intentional infliction of emotional distress from publications that could not reasonably be taken as stating facts.

“At the heart of the First Amendment is the recognition of the fundamental importance of the free flow of ideas and opinions on matters of public interest and concern.”— Chief Justice William Rehnquist

Gregory Lee Johnson burned an American flag at a political protest. Texas convicted him. The Supreme Court reversed it 5-4, ruling that even deeply offensive symbolic expression is protected speech.

“If there is a bedrock principle underlying the First Amendment, it is that the government may not prohibit the expression of an idea simply because society finds the idea itself disagreeable or offensive.”— Justice William Brennan

Congress passed the Communications Decency Act to censor "indecent" and "offensive" speech on the internet. The Supreme Court struck it down unanimously, ruling that online speech gets full First Amendment protection.

“The interest in encouraging freedom of expression in a democratic society outweighs any theoretical but unproven benefit of censorship.”— Justice John Paul Stevens