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It's tough, I would have to break it into two, Software and Hardware.

Software:
Gen 3, the software became more complex and diverse... I cut my gaming teeth on a C64 and while I was not a gamer at that point, I wanted my games to be more. I am not a graphics whore and I don't know how else to explain it, but the NES was able to make the games look and feel right. Gen 3 made me fall in love with the hobby.

Gen 4, while also great really owes a lot to Gen 3 as it's often referred as the gen that saved gaming, well the NES really but you get the point. Gen 4 took what Gen 3 did and built on it's foundation.

Hardware:
Gen 6, yes going from 2D to 3D was great, but it was also ugly. Again, I am not a graphics whore, but that does not mean I can't tell what looks good and what does not. Gen 6 took what Gen 5 did and ran with it! Gen 6 revolutionized the gaming industry, it gave 3D graphics the teeth they needed! It made gaming look beautiful! I remember my Dreamcast, had a PS2 pre-ordered at the time, but a great deal at a pawn shop made me join Gen 6 a little sooner than I had planned. When I popped in that disk of Demo's that came with and loaded up Sonic Adventure I was amazed! I had never in my short life seen gaming look so damn beautiful. The reason I give Gen 6 the nod instead of Gen 5 is simple, Gen 6 had the hardware to pull it off! We also had this gen introduce online gaming to console gamers.

Gen 6, much like Gen 4 built on the massive advancement of the previous gen. And while Gen 4 and 7 are probably my favorite they would not have been what they were had it not been for Gen's 3 and 6,