Humbug, all the good stuff is too expensive. I’d buy the Thackeray Pleiades for $75, and spend the remaining $425 on something reasonably priced to drink at home.
1995 Chave
As Robert said, if someone gave me $500 and I had to spend it, it would probably be the 1990 Leoville Barton.
If it is my money, I am all over Chateau des Tours on page 34.
+1 for the '95 Chave.
And $450 for the '12 Sassicaia is absurd (not that it should be getting drank now, mind, but jeeze).
90 monte bello or 95 Chave
Three possible for me:
1990 Monte Bello
1986 Gruaud-Larose
2001 Philipponnat Clos des Goisses Brut
The strength of this list is clearly in France, so . . .
Chambolle-Musigny Les Cras Méo-Camuzet Frère et Soeurs 2005 400.
Chambolle-Musigny Les Gruenchers Domaine Dujac 2004 320.
Chambolle-Musigny Les Hauts-Doix Robert Groffier 1996 435.
Chambolle-Musigny Les Hauts-Doix Robert Groffier 2002 420.
Nuits-St. Georges Clos des la Marechale J-F. Mugnier 2005 325.
Volnay Santenots du Milieu Leroy 2001 410.
Chambertin Grand Cru Pierre Damoy 2007 480.
Charmes-Chambertin Grand Cru Armand Rousseau 2009 445.
Mazis-Chambertin Grand Cru Armand Rousseau 2008 390.
Bonnes-Mares Grand Cru Robert Groffier 2005 435.
Clos Vougeot Grand Cru Jean-Jacques Confuron 1990 450.
Jaboulet Aîné La Chapelle 1989 480.
Château Gruaud-Larose 1986 480.
Château Léoville Barton 1990 425.
Ridge Vineyards Monte Bello Santa Cruz Mountains 1990 490.
Find 3 other couples with the exact same constraints and buy this:
Dominus 1985 (Double Magnum) 1856.
Not a recommendation (since I was just seeing it at retail for $160):
Massolino Vigna Rionda Riserva 1999 575.
Restaurant wine lists are so overpriced. I would not play the game. At the high end, I might get the Morey-St. Denis Cuvée des Alouettes Domaine Ponsot 2007 for 210 and come home with $300 extra. But, I would probably get something like the Lopez de Heredia Viña Tondonia Reserva 2002 for 105 and bring home an extra $400.
Another neat idea would be a 1/2 bottle of Puligny-Montrachet Les Tremblots Hubert Lamy 2010 for 75
and a 1/2 bottle of Nuits-St. Georges Clos de la Marechale Jacques-Frédéric Mugnier 2007 for $115 (for right now, I would generally prefer a 2007 to a 2005, which is much more expensive on the list).
I am completely biased, but
Kongsgaard Napa Valley 2012
90 leoville Barton, the 76? Maybe 78 Leroy, or the 86 leroy
So much great riesling at the cheap end of the list it’s like they’re actively trying to dissuade you from spending so much. But if you apply the White Wine Doesn’t Count rule, then my thoughts are:
- Raise the budget and get the '01 Leroy Boudots at $770. Gorgeous La Tache-like wine that would cost more to buy than it costs off the list. Or the '02 Lignier Clos de la Roche at $525.
- 1995 Chave at $435
The '86 Gruaud is wonderful of course, but why pay $480 when you can still get as much as you want at auction under $200?
This is a fun list to page through. There is so much irrational pricing and random craziness. 2006 DRC 1er Cru at $2000, more than multiple vintages of the Grands Ech! A wine from Lebanon that isn’t Musar! Probably a lot of Easter eggs in here if you give it a close read.
Along the same lines as what Keith noted, at some of these Michelin 3 start-type restaurants, say like a Jean-Georges NYC that I just recently ate at, I glance at the list, roll my eyes and move on. I’m really there for the food. And much of what I want off the menu actually pairs better with a white. At JG Park City last year I ordered a lovely Huet for $95, and then at JG Park City, ordered a Matthiason white, also under $100. The food was the highlight, not the wine. I could not see myself dropping sick money on the reds, especially where most of them were either relatively new releases or ridiculously priced mature wines. If I go red, I probably grab the Joguet, the 2009 Voge, or what Ian recommends. A red at $500, plus tax, plus tip, now you’re at $635. I pass.
A difficulty for me as well at these kind of restaurants is that my wife really does not drink reds. So I’m looking for 375s or again, going with a white that she enjoys. Just noticed that the list has Merry Edwards in 375. That makes my wife happy. At $60, no brainer.
Matt
Isn’t BYO typical for the auctions?
Nolan, I’ve never bartered for a better price on a wine list, but if I had a pre tax budget of $500, and I saw that wine on a list for $550, I’d give it a shot. It’s an amazing wine.
1990 Monte Bello as a red
1995 Comte Lafon Meursault as a white.
(emphasis mine)
i was hoping crowd-sourcing the list would help shine a spotlight on the eggs!
yes! i’m ordering off the list this weekend to get LEY points…probably stupid, but i need to regain elite status with Lettuce!
64 LDH Tondonia Blanco
I would choose one of the following, depending on your taste:
Bernkasteler Doctor Dr. Thanisch Mosel-Saar-Ruwer 1971
Chambertin Grand Cru Pierre Damoy 2007
Bonnes-Mares Grand Cru Robert Groffier 2005
1995 JL Chave Hermitage
Emilio Moro Malleolus de Sanchomartin 2005 (worse value multiple in terms of cost markup, but still may be the best wine you can buy for the $500)
Continuum 2012
Morlet Coeur de Vallée 2012 (if it’s the Beckstoffer To-Kalon, which I believe it is)
Sine Qua Non 
2013
Sine Qua Non Stein California 2012
Btw, I tried to ‘spend to the limit’ but as some others said, if it were my money I’d be inclined to spend around $100-180 for a decent bottle off that list and pocket the rest for a nicer bottle at an auction.