ZwaanME: When GOG introduced the movie section they claimed that their goal was to bring us "cinema classics" and "all-time favorite TV series" (their words, not mine). We've not seen a TV series yet and I find it difficult to call the documentaries on offer "cinema classics". GOG indicates that major Hollywood studios are unwilling to 'play ball'. But were are movies from independent studios like: Solaris, a Scanner Darkly, Donnie Darko, Night of the living Dead, Lost in translation, Bad lieutenant, Erasorhead, Memento, Clerks, Pi, THX-1138, Blue Velvet, the Usual Suspects, Dark Star, Little Miss Sunshine, Cube, Pitch Black, Swan (to name just a few titles)? These weren't made by big Hollywood studio's and are certainly widely regarded as cinema classics. I'd buy any of these titles without hesitation.
With only a few exceptions, all those movies you list are currently held by major movie distribution companies. They may have been made independently, but their distribution was handled by the likes of Fox, Warner Brothers, Sony, subsidiaries of those companies, etc. As long as the big guys hold the distribution rights, GOG is going to have a difficult time getting them to offer their films DRM free. Most of the movies GOG currently has available were both made and distributed independently, with no major studio involved in any aspect of the film, making them much easier to offer on GOG. Heck, at least one of these documentaries originally premiered on YouTube, that's how truly indie these films are.
For reference, here is how your list breaks down on distribution rights:
Solaris - Janus Films (Criterion Collection)
A Scanner Darkly - Warner Independent Pictures (Warner Brothers)
Donnie Darko - Newmarket Films
Night of the Living Dead - Walter Reade Organization
Lost in Translation - Focus Features (NBC/Universal)
Bad Lieutenant - Aries Fillms
Eraserhead - Libra Films International
Memento - Summit Entertainment (Lionsgate, though much of their distribution is administered by partner NBC/Universal)
Clerks - Buena Vista Pictures (Disney)
Pi - Artisan Entertainment (Lionsgate, again, NBC/Universal indirectly)
THX-1138 - Warner Brothers
Blue Velvet - Paramount Pictures
The Usual Suspects - originally Gramercy Pictures, which is now owned by Focus Features (NBC/Universal)
Dark Star - unknown, all the original distribution companies are defunct, which raises it's own familiar problems for GOG
Little Miss Sunshine - Fox Searchlight (20th Century Fox)
Cube - Trimark Studios (Lionsgate, again, NBC/Universal)
Pitch Black - Universal Pictures
Swan - I got no idea, looks like this one never saw a release outside the festival circuit
The only ones that seem likely to get a release here without major studio/distributor support might be Donnie Darko, Night of the Living Dead, Bad Lieutenant and Eraserhead. Solaris and the rest of the Criterion Collection is an interesting possibility too. I might be wrong about this, but I seem to remember Criterion's original DVD releases were actually DRM free. The ones with unclear rights are a big question mark. They are much like GOG's quest for classic games, where the original rights holders are no longer around or who does hold the rights is a real mystery. If GOG hadn't shown such tenacity in solving those mysteries in the past, I'd think we might never see those films at all, but GOG has surprised us more than once. The rest of them, I wouldn't count on any of them showing up for a while, but once GOG can convince one of those majors to give in to the DRM free way of life, we could see a flood of new content follow.