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The last cutoff point is around 1993, though I'd say 1990 is probably closer to reality.
If you were born in let's say 1995, that's already a completely different world you grew up in. The 5 year window in that era is such a radical difference it's not even comparable, technologically or culturally.
It's a difference between seeing the Mobira Cityman brick still in use and growing up with phones that already had color screens.
It's also an entirely different world getting wasted with your friends in 2005 compared to 2010 let alone 2015. Even the demographics aren't the same you'd see on your night out.
If you want to talk about gaming the difference is probably the biggest.
Being a teenager during the early 00's and experiencing the golden era of gaming was absolutely amazing.
