Squishy, old bean, it's just Capitalism in action. The major studios, to whom DVD is important but not the main source of income, is moving fairly slowly in releasing their libraries, which often consist of thousands of old films. The worst studio is this regard is Warners, with a huge backlot of genre title in particular that they seem reticent to release. Go to
http://www.dvddrive-in.com for more on this.
One of the only major studios to aggresively flood out their libraries is MGM, the studio that's been making the least money at the box office for the last several years and who more than once has nearly face going bankrupt. So they're making what money they can, notibly by releasing low-priced (but generally nice) discs of their genre films, which they know there's a market for.
Unfortunately, the market for older movies probably isn't as strong as for newer stuff. It's entirely possible, in fact almost certain, that a studio would sell more copies of Freddy Got Fingered or Saving Silverman than of A Night at the Opera (much less more obscure films). Especially when you factor in rental stores. So these older movies are moved onto the backburner.
This is why Criterion sets their 'recommended' prices at, generally, around forty buck, ala their recent (and *highly* recommended) My Man Godfrey disc. Criterion knows it won't make money through mass sales, but they also know there's a more limited market of people willing to pay higher prices to own great films. Let me be clear, Criterio isn't raising their prices to gouge film buffs. They're setting their prices in a way that allows them to release the sort of films they do. I doubt anyone at that company is rolling in money. For the major studios, therefore, this slice of the pie is too small to worry about.