Supreme Court Justice Antonin Scalia is one of the most conservative justices of all time, a man who proudly boasts of his reactionary jurisprudence and flaunts his connection to the Republican elite. But every once in a while, Scalia’s insistence on interpreting the Constitution exactly how it was (purportedly) understood by the framers leads him to unexpectedly progressive opinions. From flag burning to warrantless searches to free speech, Scalia’s liberal streak has made a surprisingly profound impact on constitutional law.

For court watchers, Scalia’s occasional defections to civil libertarianism have an added bonus: We get to hear the court’s most trenchantly witty inquisitor grill attorneys who were expecting a sympathetic ear. With the help of Slate’s Jeff Friedrich, I’ve collected Scalia’s most incisive and entertaining moments on the bench, when the justice broke from his usual retrograde passions to defend a surprisingly progressive vision of liberty.

Flag burning

In 1984, Texas imprisoned Gregory Lee Johnson for burning an American flag in protest of the Reagan administration. Johnson appealed his case to the Supreme Court in 1989, challenging Texas’ statute outlawing flag-burning. (A ruling for Johnson would, by extension, strike down flag-protection laws in 47 other states.) According to Johnson, burning an American flag qualified as “expressive conduct” protected by the First Amendment. At oral argument, Dallas County Assistant District Attorney Kathi Alyce Drew defended Texas’ law by insisting that the American flag is “this nation’s cherished property,” and must be protected from individual desecrators. Scalia seemed baffled; “I never thought that the flag I owned is your flag,” he told Drew.

To illustrate the arbitrary nature of Texas’ flag-protection law, Scalia then attempted to divine what other “cherished” symbols the state might protect from desecration. “I was going to ask about the state flower,” Scalia scoffs—and the courtroom erupts into laugher.

From there, Drew’s arguments only grew more ridiculous. Drew argued that her state’s law was constitutional because it didn’t qualify as “viewpoint discrimination”—in other words, it didn’t censor expression based on its message. This notion, Scalia noted, was somewhat comical: The only reason to burn an American flag is to express discontent with America, so by banning flag-burning, Texas was stifling anti-American expression. In response, Drew tried to argue that one might burn a flag to “honor” the country. Scalia challenged her to describe a single instance in which that might occur. Her reply is almost painfully silly.

Scalia’s finest moment of the day came when Drew claimed that flag burners destroy the flag’s “symbolic effect” by desecrating it. This argument, Scalia noted, is contradictory: Johnson wouldn’t have burned the flag—and Texas wouldn’t have cared about his actions—unless the flag were “a very good symbol.” Texas, Scalia explained, didn’t “just want a symbol”; it wanted “a venerated symbol.” And the First Amendment doesn’t let the government promote its message by censoring its citizens.

In the end, Scalia’s vote was decisive: A bare five-justice majority ruled that the First Amendment protected the right to burn the American flag. An incensed Congress quickly passed a federal statute banning flag burning nationwide—a law which the same five justices struck down the very next term.

DNA Searches

In 2013, Alonzo Jay King, Jr., argued that by swabbing his cheek and logging his DNA in a statewide database, Maryland police had committed a search—without a warrant, as required by the Fourth Amendment to the Constitution. Maryland’s attorneys likely expected Scalia to support the challenged law, which allowed law enforcement officers to collect and store DNA from any arrestee; after all, the justice had recently voted to allow strip searches of anyone apprehended by the police. Instead, Scalia responded to the state’s opening arguments with a brutal salvo of disbelief.

Later, when Scalia thought King’s attorney was making a bad argument, he jumped in to correct him, snipping, “I wouldn’t have made the concession that you’ve made.”

Ultimately, Scalia’s vote wasn’t enough to invalidate Maryland’s law; the usually liberal Justice Stephen Breyer sided with the other conservatives to hold, 5–4, that the statute was constitutional. In response, Scalia wrote a piercing, acerbic dissent, parts of which he read from the bench. To Scalia, the most galling feature of the majority opinion was its acceptance of the notion that Maryland took King’s DNA simply to identify him—not to log his genetic sequence in a database, as it actually did. In describing this bald misrepresentation of the truth, Scalia essentially accuses the court of lying through its teeth.

Scalia then delivered what may be one of the most colorful lines in his entire oeuvre, proclaiming that “the proud men who wrote the charter of our liberties would not have been so eager to open their mouths for royal inspection.”

Violent video games

In general, Scalia is no friend to the rights of minors; the justice has repeatedly endorsed public schools’ right to censor their students. Few, then, would have predicted Scalia’s response to a California law banning the sale of violent video games to children. When Zackery P. Morazzini, the Supervising Deputy Attorney General of California, argued that California banned only “deviant” violent video games, Scalia sounded incredulous. “What’s a deviant violent video game? As opposed to—what—a normal violent video game?” he asked. “There are established norms of violence?”

Scalia also wondered why California singled out violence as worthy of censorship. When Morazzini suggested that exposure to violent images had a negative effect on children, Scalia seemed irked. Plenty of speech has a negative effect on children; does that mean it can all be banned? “What about excessive glorification of drinking?” Scalia demanded. “Movies that have too much drinking? Does that have an effect on minors?”

The justice then asked how the First Amendment could possibly be read to permit the censorship of violent expression. Justice Samuel Alito saw an entry, sneering, “Well, I think what Justice Scalia wants to know is what James Madison thought about video games.” The audience laughed—but Scalia still seized the last word.

A few minutes later, Justice Ruth Bader Ginsburg asked how, exactly, video game designers could know when their product crossed the line into “deviant” violence. Morazzini admitted video game designers had no way of knowing when their product become potentially criminal. At that point, Scalia jumped in, suggesting California create a board to review each game to determine whether its violence qualified as deviant or acceptable. “You should consider creating such a board,” he said. “I’d call it the California Office of Censorship.”

Once again, Scalia’s vote here proved decisive: He wrote a lively majority opinion for just five justices, holding that a state could not constitutionally forbid children from accessing violent expression. Two justices held that states could sometimes censor violent video games; two justices held that states always could. But Scalia’s spirited pro-speech opinion garnered the necessary votes to become the law of the land.

In the vast majority of cases, of course, Scalia sides with his conservative brethren, making it difficult to foresee precisely which ones will inspire him to join the liberals. His civil libertarian instincts are frustratingly inconsistent—but when they do emerge, they lead to a captivating and often rollicking debate. Scalia may currently be in the midst of a late-career slide into rank partisanship. But even now, it’s worth remembering that on a few key issues, his principles have helped the court narrowly avert a constitutional catastrophe.