So if you had basically unlimited funds

[MHe225]

...... Gronefeld Parallax Tourbillon .....

[ilitig8]

Here's a "short" list:
Jean Daniel Nicolas Two Minute Tourbillon
Jean Daniel Nicolas Two Minute Tourbillon
Jean Daniel Nicolas Two Minute Tourbillon
Patek jump hour minute repeater
Philippe Dufour simplicity
Peter Speake Marin Foundation Watch
Patek Philippe caliber 89
Another Jean Daniel Nicolas Two Minute Tourbillon
Kari Voutilainen Observatoire
Montblanc Meisterstruck Pulsograph
Patek Calatrava 5119
vintage Patek Worldtimer in steel
Romain Gauthier Prestige
Romain Gauthier Logical One
Gronefeld Parallax Tourbillon
Tag Heuer Mikrogirder
Greubel Forsey Invention Piece 2
Julien Coudray 1528
Christophe Claret Soprano

Oh yeah, did I forget the Jean Daniel Nicolas Two Minute Tourbillon?

Lots of Haute pieces! Buying 4 JDN Tourbillons you have knocked out 1 million just 99,900 millions to go... writing it that way gives some perspective on just how much money we are talking about.

[Hayseed Brown]

I would commission one-off pieces from manufacturers such as Patek, Lange, Journe, Piaget, Panerai, Hajime Asaoka, etc. And, yes, I would want a Panerai Cali dial. Probably in a 42mm Radiomir titanium case. Every piece would be exactly what I want. I would probably have eight watches all together. They may all be different metals as well. Stainless steel, platinum, titanium, tantalum, red gold, etc. Probably have a Patek Calatrava in stainless steel. Stuff like that. Nothing too complicated.

I'd buy a lot of watches as gifts though.

[uchinanchu]

Oddly, many material things would lose their appeal for me.
And, I imagine, I would just be way too busy to be thinking about watches, except in passing, on certain obligatory occasions - as presents, or as trinkets.

To get the answer to OP out of the way, I guess I'd start with these 2 and go from there . . .

More importantly and along your lines Chronopolitano, the question initially seemed to be a very easy one, but as I started to contemplate my actions and what I would do with such wealth, I was surprised to find my stress level rising. Part of it was because I realized what you describe would be true for me also. I mean, being able to have any/every material thing would make "special" rather meaningless at some point in time for me. And then I started on family and loved ones, philanthropic desires/dreams and the considerations of actually following through. Not as easy as I would have thought . At any rate, of course I'd like to give it a try if the money became available, but boy it wouldn't be just all fun. Then again, maybe nothing is . . .

[Martin]

First of all, a set of the most iconic vintage Rolexes. So a PN, 6548, 6538, 1605, and a bunch 1803's in different color, including stella dials to match the shirts.
Then some dress watches of ALS and Patek for daily wear. And then some of the great masters.

I'm somewhat surprised no one mentioned de Bethune yet:






And, being Dutch, some watches of the better dutch watchmakers:

[Chronopolitano]

Who doesn't wish having gobs of money?
But I think fewer people actually think about what they would do with it if they had it.
It is harder than one thinks -- to bear the burden of having money beyond a certain amount.

Even to "do good" (philanthropy, etc), it's a lot of work. One cannot simply do what Jesse did in 'Breaking Bad' - throwing money, literally, at people.

I think it would be a good idea to really think about HOW one would spend the money, before wishing for a vast sum, so as to fantasize about buying all the toys / fun in the world. All that stuff - material things - gets tiresome after a while.

I have given some thought to it, and do not wish for more than 10 million MAX for my own personal use.
Anything beyond that, I would have to consider as money that belongs to society, but is merely being routed THROUGH me.

More importantly and along your lines Chronopolitano, the question initially seemed to be a very easy one, but as I started to contemplate my actions and what I would do with such wealth, I was surprised to find my stress level rising. Part of it was because I realized what you describe would be true for me also. I mean, being able to have any/every material thing would make "special" rather meaningless at some point in time for me. And then I started on family and loved ones, philanthropic desires/dreams and the considerations of actually following through. Not as easy as I would have thought . At any rate, of course I'd like to give it a try if the money became available, but boy it wouldn't be just all fun. Then again, maybe nothing is . . .

[93EXCivic]

Pam 262 limited edition of 99 should put a $35K dent in the billions

I'd rather have this one...

[watchdaddy1]

Everything Panerai produces & a ALS

[uchinanchu]

Who doesn't wish having gobs of money?
But I think fewer people actually think about what they would do with it if they had it.
It is harder than one thinks -- to bear the burden of having money beyond a certain amount.

Even to "do good" (philanthropy, etc), it's a lot of work. One cannot simply do what Jesse did in 'Breaking Bad' - throwing money, literally, at people.

I think it would be a good idea to really think about HOW one would spend the money, before wishing for a vast sum, so as to fantasize about buying all the toys / fun in the world. All that stuff - material things - gets tiresome after a while.

I have given some thought to it, and do not wish for more than 10 million MAX for my own personal use.
Anything beyond that, I would have to consider as money that belongs to society, but is merely being routed THROUGH me.

Great expansion, thx! For me, having "more money/wealth/assets" is welcomed, but giving it a bit more thought, the best would be just to the point where I don't have quite enough to get "everything" and I'm still "wanting". Seems like I'd be easier to deal with. To take it in a bit of a different/specific direction, a close friend of my wife is very, very wealthy (read plane, multiple homes, etc) but when we visit one of the homes, as large as it is, there is so much "stuff" that was just bought because it tickled a fancy at the time but now just sits in the various rooms and storage space. It's almost claustrophobic, even tho the home is open air and right on the beach . . . .