The layout I'm trying to achieve is shown in this image:
The HTML below is one of many attempts which haven't worked. The project this is for is targeting HTML5 in the latest browsers only, so there is no need for it to work in anything except the latest Chrome, Safari, Firefox and (with a following wind) IE9 beta.
<!DOCTYPE html>
<html>
<body>
<div style="border: solid 1px red; width:600px; height: 600px">
<span style="-webkit-transform:rotate(-
90deg);display:block;position:absolute;bottom:600px">My Vertical Text</span>
<img src="http://www.gizmodo.com/assets/resources/2007/01/Bill-gates-mugshot.jpg"
style="position:absolute;bottom:600px" />
</div>
</body>
</html>