Hi Shelby,
Yes this is a somewhat simple set-up compared to much of Roy's more complex set-ups for his documentary style fashion work. Looks to be a 4X6 softbox higher-up camera left (maybe on a boom arm) and perhaps an egg-crate grid, plus possibly a white flat or larger box positioned camera right for fill (zoom in on the image and you'll see a larger but more subdued camera right source in the male subject's eye). Don't know if the light fall-off camera left is due to a flag or was done later.
Here is a behind the scenes Vanity Fair video of him shooting Elizabeth Banks as Marilyn Monroe which has to be fairly recent. I believe Roy is under contract to conde' Nast fashion publications (Vogue, W, Glamor, Allure, etc. but shoots mostly for Vogue I think).
Video: Elizabeth Banks as a Thoroughly Modern Marilyn | Vanity Fair
On this shoot it appears he's using the Mammy 67 with prism, and film as you suggested, (there is even a quick frame of him shooting a polaroid). He may have used film for this shoot to mimic the Monroe era. There are some tasty Matthews crank controlled boom set-ups in the background, and definately some major Profoto Packs, probably for the nano-second recycle.
However, this video shows him apparently shooting with digital: (see time code @ 1:22 into this video at the end of the article:
Behind the scenes with Jane Iredale in September Vogue
Evidently, he can use anything he wants ... he seems to have purchased a condo in West Chelsea NYC for 3.38 Million :shocked:
Norman Jean Roy | 245 Tenth Avenue | High Line
On a related note: I'm friends with another major NY fashion/commercial shooter that even appeared in a segment of 60 minutes on America's obsession with beauty and fashion ... and he also shot mostly film. However, unlike us mere mortals, he had all kinds of support people and they even developed the color film right there in his Gramercy Park studio while the shoot was still under way. However, I know my friend also shoots digital, and even did a major international Nokia campaign using a P&S camera which was terrific.
-Marc
BTW, for other interesting behind the scenes videos on lighting go to the Profoto website.
Videos