But you do the cocaine before you get the hookers!

I thought you do the cocaine off the hookers' bodies.

Modest apartments in all the cities around the world I love to visit; 1st class airfare (or private jet); luxury watches; scholarship endowments to my numerous schools; medieval manuscript collection to donate to my alma mater as a collection upon my death; Scottish whisky distillery near my estate in the Highlands.

Probably spend it all on security to protect me from kidnappers...

Form my own corporation complete with its own army and attack my enemies like I was David Xanatos.

In my spare time I would attend to my shirtless man harem.

Also help the poor blah blah blah.

Vote Republican

The first thing I'd do would be to go to every room in my house and turn up the heat.

Then I'd start looking for real estate someplace.

Get my house off-grid, invest some of the money in a diversified portfolio to live off the interest, travel a bit, and get a small home in Saitama in which to live part of the year.

Hang around the Billionaire's Club telling stories of my adventures, until that no-good Flintheart Glomgold comes in boasting that he's heard tales of a lost valley full of treasure and he's going to get there first so he can become richer than me, and then I'm all "OH NO YOU DON'T, LADDY," and it is ON.

Also get a boat.

I get lonely whenever I'm living by myself so I'd probably just fill up my kitchen up with pinball machines like it was before when I was a thousandaire. I'd probably get some quality LSD too, but other than that, I'd just leave it on the street at a bus stop when it's not windy. Giving to charitable organizations is a nice thing, but more money goes to to people who work for them than the people they work for. That's natural of course, but I'd rather just conduct a social experiment in my own kinda nonprofit.

Then again I'm fucking freezing. I'd also pay my electric bill :(

Hookers and weed.

Set aside a large chunk for a comfortable retirement, give a shitload away to animal shelters, PBS, Planned Parenthood and the like.
Also, what betabox said.

I would become a real estate mogul in my home city, and help establish as many new buildings as I could that were actually good design instead of the shit we get from the "Friends of Burnside Council". This would include residential homes, apartments, shops, bars and community stuff like sports i like, or film schools. All this shit would keep me busy like a full time job, and to unwind I would still play games and masturbate, only I would be able to pay someone to masturbate me, for me. (Might have been easier if I just said hookers).

GI Blow