Okay so you're a young guy aren't you.
Chevrolet came out with their first modern V-8 in 1955. It was a 265, which grew to 283 in '57 and 327 a few years later, 350 in '68 and 400 about '70. 307 was common starting in '68 or '69 and later in the 70's there was also a 262. And of course we can't forget the 305, though we might want to.
Starting I think in '58 Chevy released their first 'big block' motor as a 348. The valve covers have a distinctive look and lead to the name 'w motor'. About '62 the 348 grew to a 409. The old Beach Boys hit 'She's so fine, my 409' is about a car with that motor. If you don't recognize that song I'll cry.
During 1965 Chevy installed both 409 and 396 motors in some cars.
The 396, 402, 427, 454, 502 and 572 are all basically the same externally. The 454 is externally balanced, I'm not sure which others might be. But basically if you can fit one of them in something, any of the others in the same place.
If you have a limited budget I'd recommend a 350. You might happen on a steal on one of the others, but if you do, you'll probably find just getting all the right pieces and accessories will be a budget killer. The 350 will be the cheapest to buy, install and run.
My quick Chevy V-8 history probably missed something and I may be off a year or two on some of the details, but the general concept is right. Now if you want to know anything about the next gen motors of the 90's and since, I'm not your guy. I don't know anything about them.