It's hard to say about stuff back in the day compared to now so I'll just say that my 2 favorite "old school" smokes were chocolate thai and afghani hash. The chocolate thai was some kind of imported bud, very dark green and compressed. Light green when you broke it open. Smelled like pine and hash. It would lay me out for hours. Same with the afghani hash. In the early 1990's I aquired a 2 ounce chunk of dark hash that was pretty hard. It had a small, red wax seal melted into it in the shape of a star. Sometimes when I make super dank bubble, it comes out spicy vs fruity and the smell reminds me of the afgani hash. My bro and I spent an entire summer consuming that brick one hot-knife rip at a time. Amazing stuff. Hash was hard to come by then, too, so that probably added to the experience.
My all-time new school favorites are Super Silver Haze, Arcata Trainwreck, AK47, and pretty much any of the more potent strains that are grown really well. The absolute dankest smoke I've had in recent memory was some outdoor Super Silver Haze from southern humboldt (2009 harvest). The look and smell on this herb was so killer a lot of people would be fooled that it was indoor. The bud was sticky to the touch and so spicy and dank tasting. The potency was through the roof . .unlike anything I've had in a long time, indoors or out. The next 'dankest' was some indoor headband that I tried a few months ago from a really, really sick indoor grower. These nugs didn't even look real! But they still didn't have the mind-melting 'KaPow' of that outdoor SSH.