Classical

How does one even begin with this behemoth of a genre? Even if I DO download the list of megas (188gb in total btw) from /classical/, where does one even start?

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Start with listening to Mozart and Haydn's piano sonatas.

Do I then like, literally go through the megas picking out names that sound funny or stand out?

Romanticism is probably the easiest one to get into, or just check out a time period or artistic movement you're interested in. Personally I started with the romanticists of my own country because they're so easily relatable. Bach, Mozart and Beethoven are called the big three for a reason and give a nice view of their eras. But don't be afraid to jump around at first, once you start to recognize the differences between the composers and eras it gets easier to look for the type of music you want. Remember that there's nothing wrong with listening to the more popular pieces, even if you feel like you've already heard them plenty of times you probably haven't heard them in the whole length and while putting some thought into it. Reading about the music can also help you appreciate it more, because you can put the compositions and composers in their historical context and understand why they were important and maybe also understand the theoretical perspective better.

I'm not an expert on classical by any means but that's how I got into it. The start is the most difficult part.

Tchaikovsky and Shostakovich. They may as well have been rock stars. Easiest place to jump in.

Try this
youtube.com/watch?v=VwwTCtYtbrg

It's like with any other genre. Start listening with whatever you like because you'll get bored otherwise.

Classical is not a "genre" and you won't get into it by treating it like one

It is like asking where to begin with popular music, there is no easy answer

He asked how to get into Classical, not how to die.

I'd say listen to the Symphonies of Tchaikovsky, Brahms and Beethoven and then maybe some 20th century composers like Stravinsky and Shostakovich

I'd say try as much variety as possible. Either split it into eras or maybe solo / chamber / choral / orchestral / symphonies then try a few works from each, find which you enjoy more and then explore further within.