I'd go back to '93. Vs. had just been released, Jurassic Park was in theaters, the US dollar had almost exactly double the buying power it has today, and I still remember how to design web sites using tables.
Event television would be a big thing. I was a senior in college in 93. Seinfeld, Simpsons, Frasier, you had to schedule your day around that. The bar I worked at would even put these shows on instead of playing music and market it as a reason to come in.
Yes, we could record shows on VHS and watch them later, but that was mostly done with daytime soap operas - also a thing that has mostly gone by the wayside.
Landline phones with answering machines would throw a teenager from today into chaos.
Smoking everywhere. Not even California had introduced smoking bans yet.
No TSA. Flying was fun.
Weed possession was a decades long sentence.
You could play around with all kinds of things that were different.