So what's the 'Eiffel Tower' or 'Colisseum' of Tokyo?

I get this question a lot. And when I can't answer it, it seems to turn people off to Tokyo. Lately I've been giving Tokyo Tower and the Meiji Shrine as answers to appease prospective travellers. The truth is, Tokyo is less about cramming in 5 museums and 10 cathedrals in one day than it is about experiencing the crazy, super-urban chaos that somehow remains amazingly well-ordered.
Most of the first-time travellers to Japan who ask me this question have already travelled extensively through Europe, where the major cities have enough monuments, churches, museums and scenic walks to fill several weeks of non-stop touring. While Tokyo has its share of temples and museums, I don't think it's fair to approach it as though it were "Japanese Paris" or "Japanese New York" (for something comparable to Paris, I'd recommend a trip to Kyoto). One of the things you have to understand about Tokyo is that throughout its history, it has been razed to the ground and rebuilt several times, twice within the past 100 years. The city is designed to move and change with time and nature.

While you don't want to miss Tokyo Tower, the Meiji Shrine, Asakusa or the Tokyo Edo Museum, the more memorable experiences will probably be found while you're out and about shopping, eating, or riding the metro. Because one of the great things about Tokyo is that though it looks like you're just getting the same thing you would in New York, it's extremely different once you poke through the surface. Domino's Pizza is *everywhere*, but it's topped with squid, corn and mayonnaise. McDonalds is also *everywhere*, but unless you specify otherwise your burger is going to come with a splash of teriyaki sauce and a nice big ice-cream scoop of mayonnaise (mayonnaise is a recurring theme in a lot of westernized food in Tokyo). Lenôtre and Paul, two major French bakery chains, have several stores in Tokyo, but most of the pastries they sell would never be seen in France (spicy cod-roe brioche, anyone?).
Most travellers would probably recommend avoiding shopping malls in Europe. They look just like American malls and it takes time away from more interesting things, like cathedrals. However Tokyo's shopping malls are different. The range of products is amazing, and you'll see several things you'd never dream could exist. Try spending an afternoon on Takeshita-dori in Harajuku. This open-air mall-like street has one of the most interesting collections of clothes, accessories and knick-knacks I've ever seen, not to mention better crepes than you can find in Paris.
I have one absolute must-see for the westerner who has never been to Japan - Transfer at Shinjuku during rush hour. Keep in mind you must be in excellent physical condition to do this, and you must have a contingency plan, because if you're doing it in a group, it is extremely likely you will be separated. Shinjuku is the busiest train station in the world, and passing through during rush hour can be a more profound learning experience than the Louvre. It may seem counter-intuitive to purposely go to the most crowded spot on the planet during the busiest time of day, but it's something that does not happen anywhere else in the world. Try it, you will see what I mean.

So have fun in Tokyo. You'll have an amazing trip. Just don't think of it in terms of monuments, churches and museums, it's a super-urban, surreal experience. And please, don't ask your friends who live in Tokyo what the 'Eiffel Tower' or 'Colisseum' of the city is. They'll only roll their eyes and say, "The Meiji Shrine" to be polite.