Actually I think the longest standing online poker room is the original poker.com/ now ThePokerClub.com. I think Paradise came later.
Planet came out in 1998, this much I know for sure. A lot of rooms came online in 1999 but a lot did not start real money play until much later, as late as 2001 in many cases.
In 1999 there was Planet and Poker.com, I think around the same time late 99 early 2000 there was PokerSpot and Paradise then a whole bunch others. They all started popping up all over the place.
It would be one of the two as the oldest room still in business: ThePokerClub.com or Paradise. Interestingly enough they both were independent rooms at one time and both ended up joining a network.
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