If you were a Lloyd Cole fan after the turn of the millennium, it became something of a guessing game each time he released a new album. Would this be a set of literate and well-crafted pop songs like 2006's Anti-Depressant and 2010's Broken Record? Or one of his experimental synthesizer projects, such as 2001's Plastic Wood and 2013's Selected Studies, Vol. 1? Well, with 2019's Guesswork, Cole has decided to give us a little bit of both. Those who favor his clever, sometimes arch, often witty perspective on human relationships and the society we call home will be happy to learn that Guesswork features eight fresh songs that find him writing and singing near the top of his game. But this time, the melodies are performed on a variety of vintage synthesizers and rhythm machines, many of which give this album a sound that's sleek and evocative, but a decade or three out of date. In this context, the arrangements and production work like a charm; this frequently sounds like an electronically generated look back to the glory days of Cole's work with the Commotions (especially in the clicks and tishes of the rhythm programs), very different in style but clearly reflecting the same time period. Guesswork could easily be passed off as a lost synth pop album Cole made and shelved in 1988. However, the music nods to the era that produced some of Cole's most celebrated music, but the lyrics do not. These stories are the work of an adult who knows more than a bit about disappointment and the kind of regret that comes at the end of a relationship, though "We could pool together and be half-right all of the time" from "The Over Under" is one of several moments where he shows he can be downcast and wry at the same time. Guesswork is the sound of Lloyd Cole older but not as wise as he would wish, yet with his typically strong melodic game sounding crisp and pleasing in new electronic dress, it's his way of trying to have it both ways and succeeding.
AllMusic Review by Mark Deming