(I find it to be kind of funny that his case is being heard before the highest court in the land.)

Washington — A clash between Jack Daniel's whiskey and a pet company selling a poop-themed dog chew toy landed before the Supreme Court on Wednesday as the justices wrestled with when a parody of an iconic brand crosses the line from First Amendment protected speech into a trademark infringement.

The legal battle involves a line of dog toys, called "Bad Spaniels," made by Arizona-based VIP Products. The chew toy at issue closely resembles a Jack Daniel's whiskey bottle but instead incorporates some poop-themed humor. Where the whiskey bottle says "Old No. 7," the dog toy says "Old No. 2," and instead of "Tennessee Sour Mash Whiskey," the chew toy reads "on your Tennessee carpet." For the references to alcohol content, "40% ALC. BY VOL. (80 PROOF)" became "43% POO BY VOL." and "100% SMELLY."

VIP Products added the Bad Spaniels toy to its "Silly Squeakers" line in 2014, when the company's owner Stephen Sacra was inspired by the whiskey's distinctive square bottle and black label while sitting at a bar. Sacra said the intent of the toy was to create a parody product that amused the public, according to court filings, and VIP borrowed "only enough to make the joke work."

But Jack Daniel's was not amused, and it sought to stop VIP from selling the Bad Spaniels toy under federal trademark law, claiming it likely confused consumers and infringed on its marks and trade dress, and tarnished Jack Daniel's reputation by associating it with dog poop.

"Jack Daniel's loves dogs and appreciates a good joke as much as anyone," lawyers for the company told the Supreme Court in a filing. "But Jack Daniel's likes its customers even more, and doesn't want them confused or associating its fine whiskey with dog poop."

A federal district court sided with Jack Daniel's, but the U.S. Court of Appeals for the 9th Circuit reversed, finding in part that the liquor company's designs were used by VIP Products to convey a humorous message that was protected from trademark-infringement claims under the First Amendment.

Jack Daniel's appealed the 9th Circuit's decision, and the court said in November it would jump into the fight.

The dispute stands at the intersection of free expression and trademark law, and a key question is whether parody is considered protected speech under the First Amendment.

"In our popular culture, iconic brands are another kind of celebrity. People are constitutionally entitled to talk about celebrities and yes, even make fun of them," Bennett Cooper, who argued on behalf of VIP Products, told the Supreme Court.

Bad Spaniels, he said, is an attempt to poke fun at how seriously iconic brands take themselves.

"VIP uses a pretend trademark and pretend trade on a pretend label on a pretend bottle full of pretend contents," Cooper wrote in a brief filed with the court. "It is all a fiction — that is the parody."

But Justice Elena Kagan told Cooper she did not understand the parody and rattled off the list of brands that the "Silly Squeakers" line makes fun of — Johnnie Walker (Doggie Walker), Dos Equis (Dos Perros), Stella Artois (Smella Arpaw), Coca-Cola (Canine Cola) and Mountain Dew (Mountain Drool).

"Are all of these companies taking themselves too seriously?" Kagan asked. "Soft drinks and liquor companies take themselves too seriously as a class?"

Justice Ketanji Brown Jackson questioned Cooper's argument that the Bad Spaniels toy is an expression that receives First Amendment protection.

"If [you] put it on a shelf, right, then you're not using it in commerce. You're not shopping it around and potentially confusing people into thinking that Jack Daniel's is selling this," she said. "That's the whole heartland of the trademark."

Jackson later said that under the argument advanced by VIP Products, "what you're doing is saying when you're dealing with expressive work, we get a pass under the Lanham Act," the law that prohibits using a trademark in a way that is likely to cause confusion about its origin.

"Even though the standard ordinarily for trademark violations in what Congress cared about is people putting things into the marketplace that confuse consumers into believing that it's from the mark holder or sponsored by the mark holder, if it's an expressive thing, then we don't really have to do that," Jackson said of the approach from the dog toy company. "We then just scream First Amendment, and we get out of Lanham Act liability, and I don't see that in the statute."

A number of well-known brands like Nike, American Apparel, Levi Strauss and Campbell Soup are siding with Jack Daniel's in the dispute, as is the Biden administration, which urged the Supreme Court to toss out the 9th Circuit's decision and send the case back to the lower courts.

But Justice Samuel Alito pushed back on the arguments from Jack Daniel's and the Justice Department, and said some of the cases highlighted in briefs raise "serious First Amendment issues."

"You seem not to be very concerned about the free speech implications of the positions you're taking," Alito told Matthew Guarnieri, assistant to the solicitor general.

He also questioned whether any "reasonable person" could think Jack Daniel's had approved the use of the mark for a poop-themed toy.

"A reasonable person would not think that Jack Daniel's had approved this," Alito said.

A decision from the Supreme Court is expected this summer.