My initial response was as follows:
There are two major factors in deciding which wine to choose - 1) The vintage rating and 2) The winery/estate producer. The next big question to consider is where it will be stored protectively over this period of time.
The other suggestion would be to maybe look at purchasing 6-12 bottles that can be 'tested' along the way and track its progress in aging. When the 'last man standing' is left to finish off the lot, he can finish in tribute to those that had tasted with him along the way.
1) The vintage. If you are looking for something that can stand the test of time, you'll need to go with a red that has a very high overall vintage rating. Off the top of my head, you should look at the following: France - Bordeaux 2000 for sure, possibly '03 or the recent banner '05 vintage, Burgundy 2005. Italy - Piedmont 2000 or Super Tuscan (Tuscany) 2001. All of these have shown to be age-worthy and 10-30 years is no problem. Once you narrow down the region/wine of choice, look at the rating for those particular vintages for each one before deciding.
2) The winery/producer. For this grand occasion, I would recommend staying with "First Growths" or Premiere Cru estates that have a track record of producing banner wines in banner years worthy of long-term aging. For Bordeaux, that would be the 5 following Chateaus: Lafite-Rothschild, Margaux, Haut Brion, Latour, and Mouton-Rothschild. However, there are several others that are equally revered such as - Palmer, Petrus, Le Pin, Lynch-Bages, Chevel-blanc, just to name a few. For Burgundy (if you like Pinot Noir), again stay with the Grand Cru (highest in Burgundy) estates. There are so many to choose, but personally, I'd stay with either a Cotes de Nuits or Cotes de Beaune areas. More specifically, Vosne-Romanee (Conti) or Gevrey-Chambertin. Someone with specific Burgundy experience may be better to help you here. For Italy, stay with the super-Tuscans (i.e. blends) with names like Antinori, Sassacaia, Gaja or a few others from the Bolgheri area.
You can find many other opinions on this and welcome to do so. Some may even wonder why I left out some CA wines, but for this occasion, I feel you need to stay with tradition, and France or Italy will keep you in that.
The bigger concern is where you plan to store this. I would immediately recommend finding a reputable storage facility in your area that you know will be around for a while and/or at least have the ability to move the wines properly. Do not think that someone's dark closet is "ok" for this.
Also, if you do decide to go this route, I'd recommend going with an online auction site that can give you a seal of authenticity with your purchase. I use Winebid.com and Winecommune.com to find some good deals if you're patient.
Personally, if price were no concern, I'd go with the following:
6 bottles of 2000 Chateau Latour (100 rating) at ~ $1500 per bottle. Taste one every 5 years or so on a special occasion leaving one for the final tasting.
If I really had to do it myself, I'd go with a case (12) of a second growth that got a really high rating that is drinking well now through the next 20 or so years. For instance, a case of 2000 Chateau l'Angelus (rated 97), would run you about $2500 (or $200/bottle) and you could have a lot of fun with it over the next 20 years together leaving one or two for the last man.
Fun question and exercise...thanks for the inquiry and let me know what you end up with.
There are several opinions on this subject and I have definitely gone the more conservative route in trying to give this gentleman good basic advice with mainstream results. The reality is, proportionately there really are only a few wines that fall in to the category of long-term aging. And, as mentioned, I did not go with any CA wines mainly because of the occasion, more than the aging quality of CA wine. I do believe there are some CA wines that fall in to this category, but they are few and far between as well. Opus One and Harlan come to mind...
I think the important point to take from this exercise is that the single most important element in making this decision is the vintage where the quality (and harmony) of the fruit, the tannins, sugar, acid and ability to blend freely are at the discretion of the winemaker. Even the great names struggle to make an age-worthy wine in 'off-vintages'.
We will be publishing a world vintage quick reference chart on our site when we launch Phase II in early Nov. 2007. Keep an eye for this and I'll be writing a piece on 'last 10 year vintages' specifically when this debuts.
Until the next sip...swirl ya' later!