Streetlight Manifesto. I recommend the albums Everything Goes Numb and Somewhere in the Between.
Music
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Great recommendation. Somewhere in the Between was my introduction to the genre! So many good memories listening to both of these albums nonstop in high school, totally reshaped my whole musical identity at the time.
Mephiskapheles
Aaron Barrett of the Reel Big Fish had a side project for a while called The Forces of Evil that's got some fun stuff in a ska vein.
Professor Plum was a small ska band I really enjoyed when they were doing things (oh golly thirtyish years ago).
+1 for Skatalites, Mighty Mighty Bosstones, Reel Big Fish, RxBandits, Less than Jake
The Arrogant Sons of Bitches is one of my favorites, and not just because they spent time mic'ing a playskool xylophone for their sets. They're not as, um, clean as the Reel Big Fish but there's a ton of fun to be had with their songs.
Original rude boy ska. The best of all time:
- Desmond Dekker, "007 Shanty Town", 1967
- The Skatalites, "Guns of Navarone", 1965
- Tony Tribe, "Red Red Wine", 1969
BONUS TRACK is it ska or is it rocksteady? either way one of my favorite songs in any genre:
- Toots and the Maytals, "Sun Moon and Stars", 1969
The Toasters. They're 3rd wave ska, after The Specials, who were 2nd wave. Try the early albums. Look for the song "Mister Trouble".
Tokyo Ska Paradise Orchestra
Trojan Box Sets are great compilations that give an all over taste. Some you may have to search for but I had an excellent one which I might be able to get the Google drive link for later
I've always loved The Pietasters. They were the first show I ever went to.
If you want a punk/ska mix, Operation Ivy is excellent.
Your "very old " is second wave. Further back is legit Jamaican Ska like the Skatalites and Desmond Dekker and early Wailers.