1. Dark and Vintage Tokyo Fashions
Tokyo is home to hundreds of youth fashion subcultures ― many of them drawing on dark and vintage influences. These include Gothic Lolita, Aristocrat, Neo-Victorian and Steampunk. The trends change from year to year but one thing remains a constant ― Sunday afternoons in Harajuku Tokyo are the best time and place to find these dark hipsters.
2. Aoyama Cemetery
In the heart of Japan's upscale Aoyama district is one of Japan's biggest and oldest cemeteries. Quiet most of the year ― Aoyama Cemetery becomes party central in cherry blossom season.
3. Manga / Anime
Japanese manga and anime range from super innocent to ultra dark. Check out one of Tokyo's many manga cafes for a sample.
4. Christon Cafe
Christon Cafe is a chain of Tokyo dining bars with a dark ambiance. (warning: the service here is terrible by Tokyo standards)
5. Dark Tokyo Nightlife
If you can find the clubs where the Harajuku kids lurk at night ― they are well worth a visit. (not easy to find: clubs shift with the wind and all information is in Japanese)
Near the east exit of Shinjuku station lies Japan's biggest redlight district - Kabukicho. Dark indeed. (keep in mind that this is a dangerous area ripe with yakuza, crime, scams and STDs)
7. Pictures of the Floating World (Ukiyo-e)
Ukiyo-e are Japanese wood block prints. They can roughly be thought of as vintage manga. Many are highly acclaimed artworks. Much like manga they are steeped in sex, crime and historical lore. Check out the Ukiyo-e Museum in Toyosu.
8. Japanese Horror Films
Japanese Horror Films are often based on Japanese mythology and urban legend. Many of them are bone chilling. Why not check out a Japanese movie in Tokyo. (luckily horror films often make sense without subtitles)
9. Love Hotels
Love Hotels are not as dark as they might seem. They are used by virtually everyone in Japan including married couples.