"[…] I'm curious at what point in the process you decide to go with an illustration as opposed to a photo/still, and how soon you decide on an artist once that decision is made. Also, does the idea of matching a favorite illustrator to a certain filmmaker ever precipitate an illustrated cover over a photo cover?"
I thought that was an interesting question. My probably-less-interesting answer is: it depends.
Sometimes the idea of illustration precedes knowing exactly who should illustrate it--like, for example, Wise Blood or Topsy Turvy, where the concept ("'50s-style literary paperback" and "topsy-turvy head made up of Gilbert and Sullivan," respectively) came first and we had to find someone to execute it. Of course, Josh Cochran and Yuko Shimizu both made those projects their own in fantastic ways.
Sometimes we don't have a specific idea of a concept but we know a particular artist will be a great fit and we can trust them to do their thing--like Seth on Make Way for Tomorrow, or Darwyn Cooke on Monsters and Madmen.
Sometimes it's a combination of the two--I had a very specific idea of what I wanted for Divorce Italian Style but it absolutely depended on Jaime Hernandez to execute it.
And finally, sometimes it's a practical decision first--we just don't have any decent photographic art elements so some kind of illustration (or at least photo-free design, if you want to make that distinction) is the only way we'll get a cover we like. That happens less since the advent of HD transfers for everything--back in the SD-only days using framegrabs any bigger than 1/2 a page was pushing it. These days we routinely use framegrabs (with a little digital magic applied) as full-bleed pages.
And to your point asking if the opportunity to pair a favorite artist to a particular filmmaker or film has ever pre-empted what might otherwise have been a photographic cover... sure, yeah, absolutely. I always love the opportunity to create a new icon for a film, to add something lasting to these great legacies, and illustration is often a great way to do that. Not to mention: the chance to work with so many artists whose work I've long admired is unquestionably one of the great perks of my job.
Also, some housekeeping: apologies to the folks who've been commenting on older posts and not seen their comments appear, that's a Blogger thing designed to cut down on spam comments (which otherwise get out of control on older posts). I've just updated and responded where appropriate. And to the multiple folks who've written requesting posters of various covers: apart from the deluxe art prints available here, most Criterion covers are not currently available as posters. But it never hurts to make suggestions to email@example.com!
Also, have I mentioned yet that Amazon seems to have lowered the pre-order price of Liar's Kiss to $10.17? (which I particularly enjoy because 10/17 happens to be my birthday!)
Should have a new design post ready for tomorrow…