@christoph I think few people are able to call themselves experts in classical music, I'm definitely not one of them. I did however reflect the other day a bit about how I actually got into classical music just a few years ago, let me elaborate briefly about my personal journey without getting too much OT. Maybe someone can get something out of it.
It's all so overwhelming isn't it, soo many composers, conductors, orchestras, symphonies, concertos, recordings etc. Where to start? For me it's very much about just "getting into" something, be it a composer or a symphony etc. Like I mentioned the other day Beethoven is my guy, he will never fail me. With Beethoven I would start with Symphonies 5, 3 & 9 and the recordings I recommended the other day (although 9 doesn't exist in that cycle yet), but take Bach for example, I know many others swears to Bach as I do to Beethoven, I've tried many times but just not found "my way in" there yet.
I'm sure that it will come though, and just a few days ago I actually managed to listen to an entire Bach album without loosing my interest and it was this one with the Goldberg Variations. I think that this might actually be it for me.
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Either way I'd recommend to stick with the "big names" and their major symphonies or concertos. Try to explore one at the time and see if you can find a favorite to dig deeper with and put the ones you don't fancy away for a while, it's ok to come back later when you're ready for it. It's all about discovering in your own pace. For instance I quite quickly felt that Mozart was not my kind of guy, today I can of course appreciate some of his work, but it's still not what I usually turn to.
I had tried many times before to get into classical music, but the composer and symphony (and recording!) that finally kicked it off for me was this one, Mahler's 2nd symphony with Ivan Fischer and BFO. It was so dramatic and simply irresistible.
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Then came Schubert who I think is quite a good place to start for "beginners" actually, and whose melodies are easy to get into. I remember my brother in law played "Fantasie" from the ECM recording below to me late at night while we were having a glass of rum and almost falling asleep in our listening chairs. I was completely hooked by it for a long time afterwards. I remember that I mostly listened to classical music in the car on my way to work every morning, this is something I still enjoy doing, driving to classical music (and Black Metal, but that is another story), there was a lot of Schubert in the car there for a while.
I can also recommend reading up a bit on Schuberts history which I found quite fascinating, it all made it even more interesting to have some "background" to the music and the person behind it.
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And then this album also had great impact on me, Alisa Weilerstein's Dvorak cello concerto which I just picked randomly on Spotify one day at work as I wanted to explore Dvorak, but I kept coming back to it and realizing that I liked it very much. I still today find it amazing and I have tried to find better interpretations and recordings, but I'm sticking to this one, although I feel it was a real lucky find at the time.
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I'm not sure that the 3 above albums would be "essential" in classical music history, but they really got me into the classical music space where I have since enjoyed exploring further and digging deeper. There's really an endless source of fantastic music out there. Bach... are you ready for me?!