Has to be 1990 or after. That Mariah Carey CD dropped in 1990.

Both images are more representative of mid-late 80's. (Don't forget- Super NES ruled a good chunk of the 90's). Pink shirts? Dead in the water by at least 1989. Yeah, the will smith pic could have been very early 90's, but the “Awesome” kid below is straight out of '88. Trust me, I lived it man. The 90's were a different animal.

isn't that the fresh prince of bel air?

you know he's got the sound turned down on the TV 'cause he's jammin to vision of love

OMFG, that baseball game he's playing is soooo freaking hard. I played it all the time even though I hate baseball. Its 8-bit ambient crowd noises are burned into my brain. *tweeeeeooo*

I have that rug… .

…No, literally, it's old.

THIS IS AWESOME

And he's listening to Mariah Carrey!

He's playing Baseball Stars! I love that fucking game.