I've owned a few - so I'll chime in.
I would start with the two I own because they are great cars and very complimentary.
2016 SS Convertible
1971 Pro-Touring build with 520hp 406, Hotchkis, StopTech brakes, etc.
Pics would help:
Then I would take a first gen '69 SS 396 375hp 4speed as my classic stock muscle car
Next I would add a '91 1LE Z28 5.0 / 5 speed
For the 4th gen I would get a 2002 SLP SS - make mine red please
And 5th gen ZL1
That's an easy one!