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I've been meaning to write up a kinda guidelines for those interested in coming to Japan. Before reading what I have to say, I recommend this article because it makes a lot of sense and in someway backs up my experiences as an event organizer and booking shows:
http://japanmusicmarketing.com/article3.htm
Gigging in Japan is much different from anywhere else in the world and a lot more difficult to arrange for any band on the underground spectrum. I'll start with some main points about the live house system and other details that might differ from the west and then I'll give some advice and finally go a bit into what I do and what kinda acts I'm mostly into booking. So here it goes...
Be prepared to pay your own way for everything. This means airfare, accommodations, meals, and transportation within the country.
Plan at least 6 months in advance. Live houses start booking very early and if you want to secure good dates without the hassle, then get it done early. 3 months in advance is usually too late or cutting it close.
Most venues in Japan are considered "live houses" (kinda mini-hall type places) where an event organizer rents the place out for any number of bands but usually 5 or 6 to play for the evening. After rental fees, even if there is a great turnout, there is usually not enough to pay each band and most do not walk away with anything or even having to pay to play. The event organizer usually asks bands to help cover the rental fees (hall, green room, gear, etc.) and the visiting band is waived from having to pay anything, so understand that you are getting a privilege with no obligation to help cover the cost of the event. If there is a payout, it's usually just enough to cover drinking at the after party for 4 band members.
There are also "live bars" that have no rental fees, but since the capacity is usually only 20 to 30 heads, the payout is about the same as playing in a decently packed live house.
Since I've explained the basic live house system, I'll just go into a few other details that might come as a culture shock. First of all, don't expect free drinks. As I explained above, the bar usually is separate from the event organizer. In Tokyo drinks are not usually part of the deal. But it depends on the place. Outside of Tokyo, there is sometimes a discount at the bar for bands. Oddly enough, many places have no problem with outside booze, especially for bands, and you can easily bring a bottle or 6-pack back stage and chug away.
Another thing is that there is usually no guest list or the guest list is a discount price. If you have your girlfriend with you and she's taking pictures or working the merch table, she can get a "staff pass" and won't have to pay, but that college buddy you haven't seen in 5 years, he should at least pay the guest ticket price. If he's been living in Japan for awhile he should know the score.
A small note about accommodations. Some Japanese cats will gladly help you arrange hotels and help you book cheap ones and get deals and such, but it shows a lot more savvy if you can do it yourself and not rely on anyone for help. Also, couch space is not common in Japan, there's just no room, so sleeping at a Japanese person's flat is not usual and if you do happen to get an invite, it should be considered a privilege.
The best case scenario would be to get the backing of a Japanese label. This is not so easy, but if you can get the connection, they will pay for just about everything. You might not walk away with extra cash, but you won't lose money.
Another good suggestion is find a Japanese band with a similar sound and just ask them to help booking some shows. Chances are they will be very helpful and get you some great gigs, just remember what I wrote above and don't expect any big payout.
Whenever a band asks me if they want to play in Japan, I immediately tell them they must pay their own way for everything. I can book a few shows in the Tokyo area and I also have connections in several other cities, but they should be prepared to cover the cost the whole way. I try very hard to get payouts but it's just a drop in the bucket compared to the whole cost of a tour.
If a band agrees to pay their own way, then I try to match their sound to some of the Japanese bands I know. Honestly I prefer raw primitive garage bands with sounds heavily routed in the 60's and a killer stage show with some kinda gimmicky appeal. That's just what the Japanese garage audience wants and since I do mostly garage events it's easier for me to give the kids what they want. That being said, I've helped all types of bands get gigs and if I think you're cool, I will most likely help you out... assuming you can agree to the primary condition that you be prepared to pay your own way!
Most of what I've written applies to Tokyo area. I don't consider it a proper tour if you just play 5 shows in the same city, so I tend to book bands in Yokohama or Chiba if they come for a 3 or 4 show stint and even that's cheating a bit cause it's all kinda the same city. A proper tour would be getting down to Osaka and hitting a number of cities on the way. The bullet train is expensive but will get you there on time for sound checks. Renting a car is another possibility but gas prices and highway tolls are a lot pricier than what you might be used to, so this takes a lot of planning as well.
I think I covered most of what you should think about when considering a jaunt to Japan. I've tried to be as lucid as possible and I may edit this in the future or add more in the comments. In any case, feel free to ask questions!