Part of experiencing Japan is taking in the culture and the nuances that make Japan distinctly unto itself. But I found Tōkyō to be so westernized that there were genuinely times I forgot I was in Japan. Where-as in Osaka there was no forgetting it. Osaka just seemed to serve up this nice mix of being a metropolitan city, with all the cool quirks and distinct perks Japan has to offer.
Tōkyō felt cold to me. You feel like a non-entity when you're there. The people don't seem all that friendly or engaging, and everybody seems so disconnected. You also don't feel that special. In Osaka I kinda liked I stuck out like a sore thumb. It caused intrigue. In Tokyo there are so many other foreigners that you end up fitting in and this isn't a good thing. Especially with the perception many folk in Tōkyō (particularly girls) have of 'gaijin'. You end up being ostracized and treated coldly, therefore becoming that non-entity.