In Turner v. Safley (1987), the Court established a very deferential standard for prison officials when confronted with constitutional claims by inmates. The Court said that prison officials can restrict inmates’ First Amendment rights if they have a reasonable penological justification, such as safety concerns.

In Hustler Magazine v. Falwell (1988), the Court rejected the intentional infliction of emotional distress filed by Jerry Falwell against Hustler Magazine and its publisher, Larry Flynt, for a parody it published. The Court determined that in order for a public figure to recover for intentional infliction for emotional distress, he or she must show that the defendant made false statements of fact with actual malice. The Court reasoned that because the parody could not be interpreted as conveying actual facts about Falwell, it was protected.

In The Florida Star v. B.J.F. (1989), the Court held that the First Amendment prohibits the imposition of damages against a newspaper for publishing the name of a rape victim when the press lawfully obtained the material from a government press release.

In Texas v. Johnson (1989), the Court ruled 5–4 that a Texas flag desecration statute violated the First Amendment in part because it punished people for their offensive political dissent. The Court ruled that the government could not prohibit expression “simply because it finds it offensive or disagreeable.”

In Sable Communications of Cal. v. FCC (1989), the Court unanimously struck down a federal law that prohibited indecent, dial-a-porn telephone expression. “Sexual expression which is indecent but not obscene is protected by the First Amendment,” the Court wrote.

In United States v. Eichman (1990), the Court ruled 5–4 that the Flag Protection Act of 1989 violated the First Amendment.

In Rutan v. Republican Party of Illinois (1990), the Court ruled 5–4 that government officials could not transfer, fail to promote, or otherwise adversely affect the jobs of government employees based on their political affiliation. In essence, the Court extended the patronage decisions issued by the Burger Court in Elrod v. Burns and Branti v. Finkel.

In Milkovich v. Lorain Journal Co. (1990), the Court determined that “an additional separate constitutional privilege for ‘opinion’ is required to ensure the freedom of expression guaranteed by the First Amendment.” This decision meant that there was no longer a wholesale exemption from defamation laws for anything classified as opinion.

In Simon & Schuster v. New York Crime Victims Board (1991), the Court invalidated a New York “Son of Sam” law that prohibited felons and former felons from recovering monies from any literary works that discussed their past crimes. (The law was created in response to concerns that “Son of Sam” serial killer David Berkowitz might make large financial gains in exchange for his story.) The Court ruled the statute was overbroad because it would apply to such works as The Confessions of Saint Augustine, The Autobiography of Malcolm X, and Civil Disobedience by Henry David Thoreau.

In Rust v. Sullivan (1991), the Court ruled 5–4 in favor of federal regulations that prohibited entities or doctors who receive federal funds from discussing abortion as a family planning option. The majority determined that the regulations did not discriminate against speech based on viewpoint but rather served the government’s own interests in funding speech that served its basic purposes.

In Cohen v. Cowles Media Co. (1991), the Court ruled 5–4 that the First Amendment did not prohibit a person from suing a newspaper for promissory estoppel (a promise that is enforceable because the person to whom the promise was made reasonably relied on it) when the newspaper failed to abide by a promise of confidentiality to a former source.

In R.A.V. v. City of St. Paul (1992), the Court struck down a city “hate-crime” ordinance that criminalized a law that prohibited the placing of symbols on private property for the purpose of arousing anger in others on the basis of race, color, creed, religion, or gender. Justice Antonin Scalia’s controversial opinion held that the law was unconstitutional because the city could not selectively choose to bar certain types of fighting words. Other justices agreed the law was unconstitutional because it was too broad, but disagreed heavily with Scalia’s reasoning.

In Burson v. Freeman (1992), the Court upheld a Tennessee law that prohibited the solicitation of voters and the display of campaign materials within 100 feet of polling places. The Court determined that “an examination of the evolution of election reform, both in this country and abroad, demonstrates the necessity of restricted areas in or around polling places.”

In City of Cincinnati v. Discovery Network (1993), the Court ruled that a city may not discriminate against newsracks that contain publications composed mainly of advertising. The Court determined that the city’s interests in fighting litter applied equally to commercial and noncommercial publications.

In Madsen v. Women’s Health Center, Inc. (1994), the Court upheld several restrictions on antiabortion protestors outside of health clinics. The Court’s decision was its first foray into analyzing the constitutionality of a trial court injunction limiting the free-speech rights of antiabortion protestors.

In Rosenberger v. Rector & Visitors of the University of Virginia (1995), the Court ruled 5–4 that a public university engaged in impermissible viewpoint discrimination by refusing to fund student religious publications while funding other student publications.

In Florida Bar v. Went for It, Inc. (1995), the Court upheld by a vote of 5–4 a Florida rule prohibiting attorneys from sending solicitation letters to accident victims or their family members within 30 days of such accidents.

In Hurley v. Irish-American Gay Group of Boston (1995), the Court unanimously ruled that a veterans group could not be forced to include a gay and lesbian group into its parade. The Court reasoned that parade organization had a First Amendment free-association right to determine what groups and messages they wanted to support.

In McIntyre v. Ohio Elections Commission (1995), the Court struck down an Ohio statute that prohibited the distribution of anonymous campaign literature. The Court reasoned the law was too broad because it would punish even truthful, nonmisleading anonymous speech.

In O’Hare Truck Service v. City of Northlake (1996), the Court ruled that a city could not retaliate against an independent contractor who did work for the city because he did not support the mayor’s political aspirations.

In 44 Liquormart, Inc. v. Rhode Island (1996), the Court unanimously struck down two Rhode Island laws prohibiting the truthful-price advertising of alcoholic beverages. The Court’s decision is viewed by scholars as an important commercial speech decision.

In Reno v. ACLU (1997), the Court invalidated two sections of the Communications Decency Act, which prohibited indecent and patently offensive online communications. The Court said that speech on the Internet was entitled to the highest degree of First Amendment protection akin to the print medium.

In National Endowment for the Arts v. Finley (1998), the Court ruled 8–1 that the National Endowment for the Arts did not violate the First Amendment by considering “general standards of respect and decency” before determining grants.

In Arkansas Educational Television Commission v. Forbes (1998), the Court ruled 6–3 that a public broadcasting station did not violate the First Amendment by exercising editorial discretion to exclude certain marginal political candidates.

In Greater New Orleans Broadcasting Association v. United States (1999), the Court unanimously ruled that a federal law prohibiting truthful advertising by privately owned casinos violated the First Amendment.

In United States v. Playboy Entertainment Group (2000), the Court ruled 5–4 that a federal law requiring cable operators to fully scramble indecent and sexually oriented programming violated the First Amendment.

In Hill v. Colorado (2000), the Court upheld by a 6–3 vote a Colorado statute limiting the speech rights of antiabortion protestors near health clinics.

In City of Erie v. PAP’s A.M. (2000), the Court upheld a city public indecency law that, in effect, prohibited totally nude performance dancing at adult entertainment establishments.

In Boy Scouts of America v. Dale (2000), the Court ruled 5–4 that the Boy Scouts had a free-association right to exclude a gay scoutmaster who did not reflect the organization’s values.

In Bartnicki v. Vopper (2001), the Court ruled 6–3 that a federal law imposing civil liability on those who use or broadcast the contents of illegally intercepted wire communications violated the First Amendment rights of the press who publish the information.

In Republican Party of Minnesota v. White (2002), the Court, by a 5–4 vote, struck down a Minnesota rule prohibiting judicial candidates from announcing their views on disputed legal and political issues.

In Ashcroft v. Free Speech Coalition (2002), the Court struck down provisions of a computer child pornography law that punished virtual child pornography that was created without the use and harm of actual children.

In Virginia v. Black (2003), the Court upheld the bulk of a Virginia cross burning law from a First Amendment challenge. The Court reasoned that the statute targeted a particular virulent form of intimidation that often constituted a true threat.

In United States v. American Library Association, Inc. (2003): The Court upheld 5–4 a federal law requiring public libraries and schools to install filters on computers in order to receive federal funds for Internet hook-ups.

In McConnell v. Federal Election Commission (2003), the Court upheld the bulk of the Bipartisan Campaign Reform Act of 2002, which imposed many restrictions on campaign finance.

In Ashcroft v. ACLU (2004), the Court ruled that the Child Online Protection Act, Congress’s second major regulation directed at content on the Internet, suffered from many of the same defects as its predecessor, the Communications Decency Act. The Court reasoned that there were several less speech-restrictive alternatives available to regulators.

In Johanns v. Livestock Marketing Association (2005), the Court ruled that mandatory assessments on beef producers for generic advertising did not violate the First Amendment because the federal government had its own First Amendment right to convey messages of support for the beef industry. This is the so-called government speech defense.