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Damn guys focus your answers.
It all depends on what you have, what you are willing to have, and what you want out of it. But mostly what you want out of it.
From the newest to the oldest:
If you want to get the newest experience (gen V), go with Black/White and Black 2/White 2 (choose the same color for both versions, this will give you storyline consistence). The second version is a sequel to the first one and has lots of postgame. However, the first version has the best story out of the both.
If you want nostalgia, go play HeartGold/SoulSilver (gen IV). It has some differences with GSC, but it's essentially a remake.
NEVER CHOOSE DIAMOND AND PEARL (gen IV). Go for Platinum if you want a longass region.
Out of Ruby, Sapphire and Emerald (gen III), go for Emerald. It has dem watertrumpets but otherwise it can be enjoyable. And if you want nostalgia, go play FireRed/LeafGreen, which unlike HGSS, is basically RBY with upgraded graphics and battle engine.
