title_body: Why is it every time I try an old expensive wine it's doesn't compare to a 25-35$ two year old wine I buy?
upvoted_answer: Not all wines are suitable for keeping - and the ones that may be, still require good stable conditions with regards to temperature, sunlight and so on. Assuming the 20+ years old wines you’ve had were suitable and have been stored well, there still are other aspects worth considering.
  Some districts have a ‘classical’ and a ‘modern’ style of wine making, where I generally find the modern more mainstream-friendly compared to the classical ones that typically pair better with quite specific foods.
  At the end of the day, it most often comes down to personal taste; younger wines often exhibit more power and fruit while being a bit rough around the edges - whereas older ones are more subdued as the tannin levels have decreased, allowing finer notes to appear. Having an 'average at best' sense of smell, these notes are often wasted on me unless they are very obvious.
  Example: While older Vintage Port (e.g. 1963, 1966) is regarded as more sophisticated than the newer vintages, I still prefer the sheer power of a 10 or 15 year old Vintage Port. Conversely, I always prefer older wines from famous districts such as Burgundy, Rhone, Bordeaux as they are made for storing a few years before release, making the newest vintages quite aggressive.