I got into Criterion because I love Kubrick, and some of his less popular films are only available in the Criterion Collection for region A.
So far I’ve acquired Barry Lyndon, Paths of Glory, and The Killing. The first two are great; I haven’t yet watched the third.
I also picked up Asphalt Jungle ‘cause it caught my eye on the shelf next to Lyndon. While not a great film, it was very fun, and I’d watch it again.
I might pick up Some Like it Hot once it starts showing up on sale, and I’ll certainly keep up with their new offerings in case anything catches my eye.