Penthouse is the one entry on this list that isn’t even really a “site” first, it’s a magazine, and it’s older than most of our parents. Bob Guccione started it in London back in 1965 basically to fund his art career, of all things, and by the time the American edition launched in 1969 it had turned into the thing that actually gave Playboy a real fight for its money, mixing legit journalism in with the nude spreads instead of just being pictures and nothing else. The Penthouse Pet title became a genuine cultural thing, not just an internal marketing gimmick, people actually knew what it meant.
Guccione ended up worth something like 400 million dollars off this thing at its peak, and the Vanessa Williams issue in 1984 alone reportedly pulled in something like 14 million bucks, which is an absurd number for one single print run. It’s had a rougher run since the late 90s, business decisions that didn’t pan out and advertisers pulling out, but the brand itself never fully died, it just evolved into more of an online content library and archive at this point. Ariana Marie was a Penthouse Pet, and so was Mia Malkova, which tells you the title still means something even now.
Worth checking out less for “new content” energy and more because you’re getting a piece of actual adult industry history, this brand shaped what a lot of us grew up thinking of as the classy end of the business, back when there still was one.