Let's be frank now...

...Tokyo is a butt ugly city. Yes, yes, its one of the most interesting cities in the world, but that sure don't make it pretty.

Tokyo's Top 5 (totally subjective) Monstrous Mistakes:

1. Edo Tokyo Museum (Ryogoku). A bad Lego reconstruction of something that didn't quite make it to the set of Star Wars.
2. Tokyo's Statue of Liberty (Odaiba). Don't even start me.
3. Asahi Flamme d'Or (Asakusa). It's supposed to represent Asahi's "eternal flame" but it actually looks like a very big, pointy poo that would have been a bitch to push out.
4. Fuji SpaceBall (Odaiba). Why?
5. Imperial Palace (Sakuradamon). They only let you see it twice and year, and there's a reason for that. Embarassment.

...but Tokyo is not merely a huge pile of unfortunate architecture. There are some places in Tokyo that hijack the senses in a way that doesn't make you want to plough your head into the nearest wall:

Tokyo's Top 5 Loveable Landmarks:

1. Senso Ji (Asakusa) and;
2. Meiji Jingu (Harajuku). Tokyo should build more of these bunnies. Unfortunately, Tokyo's architectural community has succumbed to the school of thought that "more experimental and 'modern' is better". Senso Ji and Meiji Jingu are nostalgic reminders of what Japanese are capable of in terms of the architecture they are famous for.
3. Mt. Fuji (Shizuoka). OK. It's not strictly in Tokyo, but on a clear day you can tell which direction is south-west without a compass. Very handy to travel in Tokyo without a compass.
4. Shibuya Crossing (Shibuya). For an aural assault on every sense imaginable. There are actually a lot of places like this (the area near Shinjuku's Alta Vision Screen is another pearler) and are an unmissable treat of an evening (and, strangely, when you are three sheets to the wind).
5. Kokugikan Arena (Ryogoku). During Sumo Tournaments, the arena is covered in bright colourful sumo flags. The perfect antidote to the dull and lifeless eyesore next door (Edo Tokyo Museum)...