Much of our day-to-day work as lawyers is serious business… methodical, repetitive, complex, and too boring to recount to the rest of the human race. Ever noticed there’s no viral “day in the life of a lawyer” video? That’s because there is no such thing.

But every once in a while, the courtroom becomes the stage for something… unusual. In the spirit of some lighthearted fun, let’s look at a few of the quirkiest legal cases from around the world.

1. The Tomato on Trial (USA, 1893)

In Nix v. Hedden, the U.S. Supreme Court had to decide: is a tomato a fruit or a vegetable?

Does it really matter? Well, the answer mattered because fruits were tariff-exempt and vegetables were not. Botanically, tomatoes are fruits. But the Court ruled they were legally vegetables, because they’re usually served with dinner, not dessert.

Legal takeaway: Sometimes, everyday context beats science in court.

2. Singapore’s Battle with Bubble Gum (1992–2004)

When Singapore banned chewing gum to keep public spaces clean, it sparked debates that lasted for years. One of the stranger legal angles? Medical exceptions, like nicotine gum, had to be prescribed.

Eventually, thanks to a U.S.–Singapore Free Trade Agreement, therapeutic gum was re-legalized.

Legal takeaway: Even gum can chew its way into legal history.

3. Beer Belly Defense (Germany, 2005)

A man caught driving under the influence claimed his body produced alcohol naturally due to a rare medical condition called auto-brewery syndrome.

Sounds suspicious? Well, he managed to present medical tests that backed him up and he was eventually acquitted.

Legal takeaway: Some defenses really are one in a million, but medically possible.

4. The Monkey Selfie (UK/USA, 2011–2018)

A macaque snapped a selfie on a nature photographer’s camera and the photo went viral. So now who owns the copyright? The monkey or the photographer?

PETA sued on behalf of the monkey, but the court ruled animals can’t own copyright.

Legal takeaway: Being photogenic doesn’t make you a rights-holder.

5. Japan’s Hologram Marriage (2018)

A Japanese man, Akihiko Kondo, held a wedding ceremony to marry Hatsune Miku, a fictional holographic pop star. The ceremony cost over USD $17,000 and included a formal exchange of vows with a talking AI hologram in a capsule. While not legally recognized, the “marriage” drew global attention and sparked public discourse about emotional relationships in the age of technology.

Legal takeaway: The law can’t stop you from marrying your dreams, but it also won’t issue a certificate for them.

The Real Lesson?
Law isn’t just about statutes and logic. It’s also about people, and people are strange, unpredictable, and occasionally hilarious. These cases remind us that no matter how bizarre the issue, the law must find an answer.

So the next time legal work feels routine, just remember: you could be arguing about vegetables, monkeys, or medically brewed beer. I’ll much rather stick to my commercial disputes thank you very much.

Sincerely,

Stephen Le, Lead Litigator