Life in the ’90s might seem innocent compared to today’s world, but many teen habits from that decade would raise legal red flags now. From casual tech piracy to risky rides in pickup trucks, what once seemed like normal teenage behavior could today be considered a crime or safety violation. Rules have tightened, laws have shifted, and society’s tolerance for certain behaviors has dropped. Let’s look back at 12 things ’90s teens did that wouldn’t fly today, and in some cases, could actually get them arrested.
1. Burning CDs and Sharing Them with Friends
In the ’90s, teens would burn music onto CDs and hand them out like party favors. It felt harmless and even generous, but by today’s standards, it’s considered copyright infringement. With tighter digital rights management laws and aggressive anti-piracy enforcement, this old-school mixtape method could now lead to fines or even lawsuits. It’s a stark reminder of how casually we used to treat intellectual property before streaming platforms took over music sharing.
2. Riding in the Back of Pickup Trucks
Nothing said freedom like riding in the open bed of a pickup truck with your friends and the wind in your face. But today, this kind of joyride is illegal in many states due to safety concerns. Laws now require passengers to be properly restrained, and riding in the back is often banned unless under specific circumstances. What felt like summer fun in the ’90s could now earn someone a hefty traffic citation, or worse if there’s an accident.
3. Buying Cigarettes from Vending Machines
Cigarette vending machines were once a common sight in diners, bowling alleys, and gas stations. Teens could walk up, insert a few bucks, and walk away with a pack, no questions asked. Now, such machines are either banned or strictly age-restricted to prevent youth access. With the nationwide tobacco age raised to 21, this once-easy loophole has been closed completely. What was once a rebellious thrill is now heavily regulated.
4. Sneaking into R-rated Movies Without ID
In the ’90s, all it took was confidence (and sometimes a hoodie) to slip into an R-rated movie. Theater staff weren’t always checking IDs, and multiplex layouts made switching screens easy. Today, with more surveillance, digital ticketing, and stricter staff enforcement, that kind of sneaky fun could get you kicked out, or even banned from a theater. What used to be a rite of passage now comes with real consequences.
5. Using Fake Names in Online Chatrooms
Before social media verification, the internet was the Wild West. Teens often used fake names, lied about their age, and entered shady chatrooms without supervision. Today, impersonating others or misrepresenting identity online can violate terms of service or even fall under laws against cyber deception. With concerns around grooming, online safety, and identity theft, this kind of behavior is no longer brushed off as harmless experimentation.
6. Drinking Underage at House Parties
Backyard keggers were practically a teen tradition in the ’90s. Police often turned a blind eye unless things got out of hand. Now, many states have “social host” laws that hold parents or homeowners legally responsible for underage drinking on their property. Teens caught drinking face stricter penalties, and parents could be fined or arrested. What once seemed like a low-risk way to party can now lead to criminal records.
7. Breaking Into Abandoned Buildings for Fun
Urban exploration, or just straight-up trespassing, was a thrill for ’90s teens. They’d sneak into old warehouses, hospitals, or schools for a scare or a cool photo. Today, that’s considered criminal trespass and can lead to arrest or injury lawsuits. Increased building security, surveillance cameras, and stricter property laws have made this teenage pastime a legal landmine. What used to be edgy fun is now seriously risky behavior.
8. Downloading Music from Napster or LimeWire
The dawn of digital music brought peer-to-peer file sharing, and ’90s teens were all over it. Napster and LimeWire made it easy to build massive music libraries without paying a cent. But this “free music” came at a legal cost. As copyright crackdowns began, thousands were sued for illegal downloads. Today’s streaming options make piracy less common, but back then, every downloaded track was potentially a lawsuit waiting to happen.
9. Smoking in School Bathrooms
Smoking cigarettes, or even worse, other substances, in school bathrooms was a classic teen rebellion move. Some schools enforced it lightly, with just detention or a warning. Today, with vaping concerns, zero-tolerance drug policies, and advanced surveillance, students caught smoking face suspension, expulsion, and sometimes criminal charges. What was once an edgy act of defiance is now taken extremely seriously by both schools and law enforcement.
10. Playing with Fireworks in Suburbs
Shooting bottle rockets and Roman candles in neighborhood streets was a summer favorite for ’90s teens. But in many places now, fireworks are banned or require permits, even sparklers in some counties. Noise ordinances, fire risks, and injuries have led to tighter laws. Teens lighting up for fun could now face fines or be reported to the police. This nostalgic thrill is now largely a Fourth of July no-go without adult supervision.
11. Carrying Pocketknives to School
In the ’90s, it wasn’t unusual for boys (and some girls) to carry small pocketknives to school, sometimes even as tools or part of a collection. Today, any weapon-like object on school grounds is a major offense. Many districts have zero-tolerance policies, and students could face suspension, arrest, or a permanent record. What used to be a harmless accessory or utility item is now seen as a dangerous violation.
12. Making Prank Calls to 911 or Businesses
Back then, prank calling a pizza shop or even 911 was a favorite sleepover activity. Teens rarely thought about the consequences. But now, prank calls, especially to emergency services, are illegal in most states and considered a criminal misuse of resources. “Swatting,” or making fake emergency calls, is a felony offense. Today’s caller IDs and call tracing mean that what was once a silly joke can result in serious legal trouble.
