I grew up a child of the 70s, discovering ska in the 80s through Madness, The Specials, Blondie, and Evan Dorkin's excellent Pirate Corp$ comics! I didn't really like third-wave ska for a looong time, except a few random Offspring tracks, until I heard Save Ferris and my mind was changed.
When Madness put out their Dangermen album and I finally saw the roots of their music through those fantastic covers, I finally came around and started learning more about first-wave ska (which i didn't realize pre-dated reggae by about a decade). I picked up a couple compilations at the library and heard my first Desmond Dekker, Toots and the Maytals, and my new favorite ska single,
Mille Small's My Boy Lollipop