Times Square is way brighter than Shibuya Crossing. Americans win the neon round.
At 360,000 pedestrian visitors per day, Times Square cannot beat the 3000 people per green light on Shibuya. Japanese have it, when it comes to perfectly organised safe and well behaved population.
In 1913, when the NY Times moved into Times Square, skyscrapers were starting to arise in the Big Apple. Meanwhile Japan's heart looked more like a village, more or less until the 80s when the darkest era hit Times Square (actually it became the worst area of NY at that time) Shibuya started to blossom. Still, we give this one to the yankees.
Everytime the green light strikes, a huge mass of people starts walking. Salaryman, yamamba, they all mix and never touch each other, in front of the amazed eyes of the foreign visitors. Despite residing in Shibuya, I never got tired of this sight... So really, Shibuya wins the pedestrian scramble title「スクランブル交差点」。
All the Disney movies and musicals signs together cannot beat the story of Hachiko, the loyal dog who waited for his owner every day, at the train station, to come back home... Shibuya is much more kawaii!
6. Crazy People
I would say even on this one - still remember the Japanese Jesus preachers on Sunday morning - but Times Square does look a million times packed with them, basically because you do understand what they say, not because there are more strange preachers of all kinds... Even on this one.
If we focus on the visitors, Times Square is the second largest attraction on Earth - after Vegas!!! Times Square generates roughly 5 billion USD in retail, shows and hotels - 20% of each dollar spent in NY by a tourist is, on average, spent in here! Completely crazy. Shibuya is a key station in the life of many Japanese, but it does not drive the same business by any means. Still, I have a lot of good ideas for shopping in Tokyo, many of these you can find around these streets of my favourite neighborhood. But OK, NY wins this one.
8. Old memories
I actually attended the opening of the American Eagle store in Times Square with Christina back in 2008, can you remember?? NY won the good old times prize! There are many memories with many good friends in Shibuya, but this one is way oldest.
9. Free amazingness
Shibuya is really the place to sit, stare, watch Japanese life past by. In front of your eyes. It is maybe not so bright, large or crowded with tourists, but these streets and the station capture pretty well a snapshot of what living in Tokyo is. Fast, unexpected, safe, organized, fun, amazing. I still miss and know that I will miss the rush everyday, for the rest of my life... But it keeps beating inside of me, as there's nothing more empowering than to know of one place where all dreams come true. At least, for the time you are there (^_^)
...Times Square probably wins most of the points which can be quantified, but it will never ever win my heart over my beloved Shibuya.