The trouble is that we've got several different questions floating around here. Most of us are only answering about the first question (from the thread title), but some are answering about the less restrictive criteria.
1) Guys who ran sub 1:50 and sub9 3200 in HS. Short list: Webb, Spivey, Sully and Brannen (if you include 3k/2mile conversions). We have a still uncomfirmed Sage.
2) Guys who ran sub9 3200 in HS, and eventually went sub 1:50 later on in life. Rupp and Hacker have been mentioned.
3) Guys that who ran sub9 3200 and went sub 1:51 in HS. Probably a few more guys on that list.
4) Guys that did any two of the following in HS: sub4:10 1600, sub9 3200, sub 1:51 800 and sub15 5k. This list is less impressive, because almost anybody who has done one has done two of these. Almost any 4:10 miler has likely run under 9, and many might have run under 1:51. Any sub15 5k guy likely ran under 9.
The trouble with questions #3 and #4 is that they're a little too easy, especially #4. If you know of a guy went under 9 or under 4:10, he's probably on that list, so guys are throwing out every sub9 guy they can think of, which defeats the purpose of the original question, which was finding guys with ridiculous range.
For the first question, we've got Webb and Brannen as the only two to have done it with 800 and 3200 times. Spivey's 2mile is quick enough to get him in. Sully's 3k is good enough. And if we're accepting 3ks, I wouldn't be surprised if Willis did it as well, along with Gregson.
The question of guys who went sub9 in HS and later went sub 1:50 is interesting, since most of the guys who were sub9 in HS but not sub1:50 in HS tended toward longer distances, like Rupp, Solinsky, Ritz, etc. Some of the guys who were sub9 in HS but focused on the 1500/mile in college didn't quite get there, AFAIK, such as Sage and Pifer. I wouldn't at all be surprised to see Fernandez, Centro, and Jager do this if they stay healthy. Centro might have already.