Parody, pet poop and product protection will be before the U.S. Supreme Court in a humorous take on a serious subject: when spoofs of well-known commercial brands go too far under federal law.

The justices will hear oral arguments Wednesday in an appeal from distiller Jack Daniel's, which is suing to stop an Arizona company from selling plastic dog toys that look similar to its iconic whiskey labels and bottles.

It is the latest high-profile intellectual property rights case at the Supreme Court. A ruling expected by June could clarify the limits of the First Amendment in such trademark infringement disputes.

At issue is the "Silly Squeakers" line of dog toys, with some that mimic well-known brands.

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Phoenix-based VIP Products markets dozens of novelty pet products, including the 18-inch "Bad Spaniels" vinyl toy shaped like a liquor bottle, advertised on its website as "Silly and Fun For Everyone!"

The high-end whiskey maker in its appeal refers to the toy as "poop-themed" and says the parody product damages its valuable brand by confusing customers.

The chew toy has the words "The Old No. 2 on Your Tennessee Carpet," a play on the Jack Daniel’s phrase "Old No. 7 brand." And while the Jack Daniel's bottle reveals that it is 40% alcohol by volume, the toy's label playfully indicates that it is "43% Poo by Vol." and "100% Smelly."

VIP says its packaging makes clear that "This product is not affiliated with Jack Daniel Distillery."

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In what passes for judicial humor, intellectual property experts and legal bloggers have been playfully previewing the case online, wondering if the high court, in a "spirited debate," will be "laying waste" to its trademark precedents; whether its ruling will have "bark and no bite."

Even the attorneys from both sides have tried a light-hearted approach in their briefs with the high court.

"Jack Daniel’s loves dogs and appreciates a good joke as much as anyone. But Jack Daniel’s likes its customers even more, and doesn’t want them confused or associating its fine whiskey with dog poop," wrote lawyers for the company to the court.

If their appeal fails, they warned that "anyone could use a famous mark to sell sex toys, drinking games, or marijuana bongs, while misleading customers and destroying billions of dollars in goodwill — all in the name of just having fun. Humor does not transform [federal law] into a trademark free-for-all."

Levi Strauss, Nike and Campbell Soup Company are among those filing amicus briefs in support of Jack Daniel's.

But the pet products company counters, "It is ironic that America’s leading distiller of whiskey both lacks a sense of humor and does not recognize when it — and everyone else — has had enough."

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"In the playful parodic tradition that has ranged over a half century from Topps’s Wacky Packages trading cards through 'Weird Al' Yankovic, VIP put out a chewable dog toy. VIP has never sold whiskey or other comestibles, nor has it used 'Jack Daniel’s' in any way (humorously or not). It merely mimicked enough of the iconic bottle that people would get the joke."

In an unusual move, VIP asked the court for permission to submit 10 of its actual "Bad Spaniels" toys for the justices to personally examine, even encouraging them to "squeak" them for effect.

Various advocates for free speech and artistic expression have filed legal briefs to support VIP Products, some arguing that "cultural signifiers" used in movie takeoffs, "fanzine" tributes and political blogs would be threatened if the law's protections were limited.

A federal appeals court in San Francisco ruled for VIP, concluding that "the Bad Spaniels dog toy is an expressive work entitled to First Amendment protection."

The Justice Department has suggested that the justices take a pass on deciding the issues at this stage and throw the case back to the lower courts to resolve some important legal questions.

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This is the second high-profile intellectual property case the Supreme Court is addressing this term.

In October, the justices debated a fair-use dispute over an image of the late music superstar Prince by the equally famous late artist Andy Warhol.

Photographer Lynn Goldsmith took an iconic 1981 photograph of the singer, which Warhol later used to create a series of silkscreen images that illustrated magazine profiles.

At issue in that case is whether a work of art is transformative if it conveys a different meaning or message from its source material, or whether courts cannot consider the meaning if it "recognizably derives from" its source material. 

A ruling in that case is due in coming months.

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The high court in both the Warhol and whiskey cases are being asked to navigate an admittedly subjective inquiry – just when derivative designs cross a line into a copyright or trademark violation, even when it involves low-brow, scatalogical humor.

Under "the fair use" doctrine, a copyrighted work or trademarked brand can be appropriated under certain conditions – a legal standard designed to foster further creativity and freedom of expression. Such "transformative" works can be used in commentary, criticism and commercial parody.

But under the key federal trademark infringement law – known as the Lanham Act – those suing typically must show, among other tings, the offending work or brand "explicitly misleads" or confuses consumers.

That standard has long been debated in the courts, and here the justices are being asked to clarify the limits in the digital age, when artificial intelligence and computer technology makes transforming art and brands easier and more pervasive.

Under the "Rogers test" used by federal courts over the years, judges are asked to balance the "right to protect [a] celebrated name and the right of others to express themselves freely in their own artistic work."

It was named after the late actress Ginger Rogers, who lost her lawsuit over the 1986 Fellini film "Ginger & Fred" about two Italian cabaret singers. Rogers claimed that the movie violated her trademark rights, but an appeals court found that expressive uses of trademarks deserve heightened free speech protection.

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What the court decides could have major implications beyond commercial products and into the current fractious political expression, with satire sites like "The Babylon Bee" and TV comedy shows like "Saturday Night Live" skewering elected leaders, ideological movements, and celebrity and corporate culture in general.

That includes the recent "culture jamming" phenomenon, which the dictionary defines as "a form of political and social activism which, by means of fake adverts, hoax news stories, pastiches of company logos and product labels, computer hacking, etc., draws attention to and at the same time subverts the power of the media, governments, and large corporations."

Well-known corporate logos and symbols are typically altered in a satiric or ironic fashion, sometimes called "guerrilla communication," because of its frequent grassroots, anonymous origins and use in flash mobs and graffiti.

Even the nine justices could indirectly expand or limit parodies of themselves.

Case in point: The court last month denied a separate appeal from an Ohio man who created a Facebook page to mock his local police department. He wanted to sue after being arrested and initially charged with violating a state law that makes it illegal to "disrupt" or "interrupt" police functions.

The "Onion" website filed an amicus brief to argue on the societal and cultural benefits of satire in political critique – making its point in an uproarious, tongue-in-cheek fashion.

When addressing the justices directly, the satiric "news" site was blunt: "The Onion knows that the federal judiciary is staffed entirely by total Latin dorks."

The current case is Jack Daniel's Properties v. VIP Products LLC (22-148).

North Korea launched a short-range ballistic missile toward the sea on Sunday, testing activities that appear to be in response to ongoing U.S.-South Korean military drills.

The North continuing its missile tests shows the country is not deterred by the U.S.-South Korea exercises it views as an invasion rehearsal, although many experts suggest the tests may also be part of the North's larger goal to expand its weapons arsenal, win international recognition as a nuclear state and have international sanctions lifted.

The missile, which was launched from the North’s northwestern Tongchangri area, flew across the country and landed in the sea off its east coast, according to South Korean and Japanese assessments, which reported that the missile traveled a distance of about 500 miles. This range suggests the missile could target South Korea.

The chief nuclear envoys from South Korea, Japan and the U.S. strongly condemned the missile launch as a provocation threatening peace on the Korean Peninsula and in the region. They agreed in a phone call to strengthen their coordination to send a firm international response to the North's testing activity, according to Seoul's Foreign Ministry.

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South Korea's military said its joint drills with the U.S. will proceed and it will be prepared to respond to any provocation by the North. During drills on Sunday, the U.S. flew at least one long-range B-1B bomber for joint aerial training with South Korean warplanes, according to South Korea's Defense Ministry.

North Korea is wary about the deployment of B-1Bs, which are capable of carrying a large conventional weapons payload. The country had responded to B-1B flights in February by test-launching missiles to ranges that showed they can reach some military airbases in South Korea.

According to Japanese Vice Defense Minister Toshiro Ino, the missile landed outside Japan’s exclusive economic zone. He said there were no reports of damage to vessels or aircraft in the area and that the missile likely showed an irregular trajectory, a possible reference to North Korea’s highly maneuverable, nuclear-capable KN-23 missile.

The U.S. Indo-Pacific Command said Sunday's launch does not pose an immediate threat to the U.S. territory or its allies. However, it did say the North’s recent launches highlight "the destabilizing impact of its unlawful" weapons programs and that the U.S. security commitment to South Korea and Japan remains "ironclad."

The launch was the North’s third round of weapons tests since the U.S. and South Korea began their joint military drills on Monday. The drills include computer simulations and field exercises and are expected to continue until Thursday. The joint exercises are the biggest of their kind since 2018.

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North Korea recently tested weapons including its longest-range Hwasong-17 intercontinental ballistic missile designed to strike the U.S. mainland. North Korean leader Kim Jong Un said the launch was conducted to "strike fear into the enemies," according to state media.

A launch on Thursday, the North’s first ICBM firing in a month, prompted strong opposition from the South Korean, Japanese and U.S. governments, as it was conducted just hours before South Korean President Yoon Suk Yeol flew to Tokyo for a summit with Japanese Prime Minister Fumio Kishida.

Yoon and Kishida agreed during the summit to resume conversations about defense and further strengthen security cooperation with the U.S. to counter North Korea.

North Korea has missiles that put Japan within striking distance. In October, North Korea fired an intermediate-range missile over northern Japan forcing communities to issue evacuation alerts and stop trains.

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Kishida issued a response to North Korea's launch on Sunday that includes working closely with South Korea and the U.S.

The North had also fired cruise missiles from a submarine the day before the military exercises began. According to North Korean state media, those missiles were a demonstration of its commitment to respond with "overwhelming powerful" force to the military drills by the U.S. and South Korea.

The U.S. and South Korea are planning to carry out more training involving a U.S. aircraft carrier later this month after their current exercises conclude, which suggests North Korea would likely respond to those drills with additional weapons tests.

The Associated Press contributed to this report.