What makes this record Trunkworthy isn’t just its insane commitment to diversity, but its raging belief in infinite possibilities.

From the first song on What Up, Dog?—a slow-burning, melancholic soul track that both laments and pays tribute to the American dream—you may be intrigued, if not hooked. But don’t get too comfortable. You have no idea what you’re in for.

The third album from Was (Not Was) then segues into two early-’80s-inspired R&B dance tracks, before moving into something that sounds like it got lost wandering off a word-jazz cut from a later-period Tom Waits record. All of it’s followed by more of the same except for the tracks that wouldn’t be out of place on a Chi-Lites or Spinners greatest hits collection, or the one Frank Sinatra-styled cut that’s sung by —you guessed it—guest vocalist Frank Sinatra Jr.

And then there’s the record’s hit, “Walk the Dinosaur,” one of the most multilayered dance songs to ever chart. Somehow the song manages to tap into the era’s love of novelty-style records without being novelty itself. It’s also driven by an infectious dance groove that actually mocks the dance and catchphrase phenomena (“boom boom acka lacka lacka boom”).

What makes this record from 1988 Trunkworthy is not just its insane commitment to diversity, but its almost raging belief in infinite possibilities and unexpected combinations and juxtapositions. Lyrical themes like self-deluded (but heartfelt) male bonding, ruminations on JFK conspiracy theories, the falsity of romantic and cultural institutions all find their place here. It’s like a K-Tel album that might have existed in a strange parallel universe where Soul Train was jointly run by Don Cornelius and Hunter S. Thompson.

This is what happens when two former Detroit musicians/music critics, David and Don Was—weaned on their home state’s variety of pre-punk MC5 and Stooges, jazz, and soul (and not just Motown)—recruit two relatively unknown but incredibly talented soul singers from local clubs, in much the same way that Daptone Records discovered Sharon Jones and Charles Bradley. All this comes with a lyrical sensibility that is sly, sardonic, and near absurdist at times. And what unifies it all is the rule-breaking sensibility of punk rock, which it musically resembles in no way. This is the very spirit that would make “eclecticism” possible, before it became a dirty—or even worse, clean—word.

The Frank Sinatra Jr. guest vocal in the midst of all this was a tip-off to their dexterity, but nothing new. Was (Not Was) had been no stranger to unexpected collaborations—previous albums featured guest leads by Ozzy Osbourne and Mel Torme. So it’s no accident both would go on to successful careers as producers. Together they produced Bob Dylan. Don Was would go on to work with everyone from Iggy Pop and The B-52’s to Bonnie Raitt and The Rolling Stones, while David would helm records by Rickie Lee Jones, Roy Orbison, k.d. lang, and others. And they both made these efforts work with the trick bag they’d honed so well.

So if you’ve never heard what Don and David did before they produced everyone else, then this is the record you must check out. Much of what they devoured as music fans finds its way on here in such unexpected and exuberant ways. Like an incredible late-night jam session, What Up Dog? surprises with every track, and just when you think you’ve figured it out, it takes a sharp turn down a street you’ve never been on before and didn’t know was your favorite place to be.