Steve Chorney - Apple/Mac book cover

Definitely before the first iphone 2007 as we see the pager and phone on the utility belt, and the laptop is a little too thick to be MBA 2008 and definitely not a clamshell 1999, so I would guess it falls into MacBook category in the year of 2006.     

I was thinking either that or a PowerBook G4, which could push it back as far as 2003. Details on the laptop aren't spot on for either, and I don't know what to make of the owl.

You might be right as he's holding it with one hand meaning it's 12".

OWL is a computational logic-based language first published in 2004.  The W3C Web Ontology Language (OWL) is a Semantic Web language designed to represent rich and complex knowledge about things, groups of things, and relations between things.

12" would also track with the keys being right at the edge of the case vs. having a large bezel. Interesting on OWL-- I have the vaguest recollection of that being a thing, but definitely seems like you could be on to something. The timing is right.

Mystery solved(ish)-- I traded emails with the artist, and this was *not* an Apple ad (as listed by HA), but actually done for a humor/satire book, making fun of liberal/left/tree-huggers (hence the owl), and this was back when using Macs was a bit of a signifier of that. That explains why the Mac doesn't exactly match the details on an actual computer (they way you'd think it would for an ad). Apparently there's a matching version for someone on the right, and I'm still not sure on the year...

I think he would have done better if he'd invested in some stock instead of complaining.