Off the top of my head, pre-1950 I have a few bottles of Madeira (all 20th century though), a few bottles of 1947 and 1949 Bourdy Chateau Chalon, two or three bottles of Toro Albala PX from the 1940s, and a 1945 Maury. I think I then jump to a 1952 Williams & Humbert Oloroso.
1996 Justin Vineyards Obtuse (Traditional) Paso Robles Port
1997 Fiorenzo Nada Barbaresco Rombone Nebbiolo
1997 Giuseppe Contratto Barolo Tenuta Secolo Cerequio Nebbiolo
2004 Big Basin Vineyards Mandala Santa Cruz Mountains Syrah
2006 Copain Syrah Thompson Vineyard Santa Barbara County
About 25 years ago I tried to convince some friends to purchase and share a bottle of the 1795. IIRC it was $800. No luck. $800 was a lot of money back then when I was saving up to buy a house.