I remember back in 1985 when I first picked up The Toasters' Recriminations EP and NY Beat comp at Sounds on St. Marks--a fairly clueless suburban kid having had no prior exposure to the NYC ska scene--but being a huge fan of The Specials and The Beat, I fully expected these records to be quite similar to 2-Tone. When I listened to them, I liked them, but I just didn't get how the dots were connected between More Specials and Recriminations. The ska sound/paradigm had changed that drastically to my ears/mind.
But Joe Jackson's "Pretty Boys" is a major link that I was missing (along with cuts from other new wave bands that dabbled in ska/reggae) which helped shape the transition from 2-Tone to 3rd wave ska.
Speaking of not "getting" a sound or a record, my brother, who for years had been way more ahead of the musical curve than I was, couldn't wrap his head around Operation Ivy's Energy when I played it for him back in 1989. (It's interesting to note that that year marked the birth of not only ska-punk, but with the release of the Mighty Mighty Bosstones' Devil's Night Out, ska-core.) I thought Energy was an incredible, groundbreaking album (and was pleased that I had finally made this musical discovery that he had missed), but he was revelling in the hard rock kitsch of Kiss at the time and completely dismissed it.
This leads to another interesting aside (which I heard first hand from both parties). Tim Armstrong (aka Lint of OPIV) originally sent a demo of Energy to Bucket in the hopes that Moon Records would release it. Unfortunately, in the late 80s, Moon was struggling financially--Bucket told me that his bed was propped up on boxes of unsold Recriminations and NY Beat LPs (which is the reason why both Skaboom! and Thrill Me Up were first released on Celluloid Records imprints Moving Target and Skaloid)--so he didn't have the cash to press and distribute it (Bay Area punk label Lookout Records did). He also admitted that even if Moon had the money at the time, he probably wouldn't have released it. He just wasn't into the ska-punk sound...
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Not quite related, but my entire day today has been trying to figure out which is better - Elvis Costello's My Aim is True or Joe Jackson's Look Sharp! They're like two sides of the same coin. One must reign supreme, but which..?!
Of course, they were both vying to be the angriest young man in England (and later in both of their careers, they go all crazy, trying on all sorts of musical genres for size--I'm a jazz guy, I'm a bluesman, I'm classical guy, I'm a big band guy, I'm a...)! Personally, I think that Look Sharp! may be a better record overall than My Aim--but then Elvis pulls ahead of Joe by releasing the blistering This Year's Model (my absolute favorite EC album), leaving Joe in the dust for good...
Weird coincidence, I just picked up the double 10" LP of Look Sharp! off eBay that even has a Look Sharp! button attached to its cover (yes it was released that way!). Never saw it back in the day (I was a pre-teen then). They can't/don't do these kind of neat things with CDs nowadays...takes a bit of fun out of collecting music if you ask me.
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