I still kinda like The Toasters
Ain't no shame in that game! "Run Rudy Run," "Decision at Midnight," "Now or Never" - amazing songs.
There was a whole bunch of great New York ska in the 80s - The Terrorists, The NY Citizens, The Toasters, Urban Blight (featuring Mackie from the Cro-Mags on drums), all the early Moon Records stuff, hell - I'd even put Fishbone in that category - it seems like they played with the Citizens or Murphy's Law every other weekend in '87-'88 (and they were amazing).
Obviously, The Specials - they still not only "hold up," but are better than most other bands ever (there've been a lot of bands throughout history, so it's not really that much of an overstatement, o.k.?).
Both Selector records are great.
Early Bob Marley/Wailers ska stuff is pretty unassailable in its awesomeness ("Maga Dog," "One Cup of Coffee," "Guava Jelly") - saying the Wailers suck because legions of idiots like them is like saying the same thing about the Beatles.
One of my favorite eras of music, in general, is when the original ska beat started slowing down, and DJs first came on the scene in Jamaica - so, like, all those great Studio One comps, early U-Roy and I-Roy, etc. (and the modern revivalists, like I-Ron, of course)...
If you go back one step further to Mento, you can kind of see the point at which what eventually became reggae split off from what was quickly becoming Calypso, too.