This is easier to show than explain: http://jsfiddle.net/gN4VZ/

Is it possible to have my right-floated content (blue) overlap my left-floated content (red) instead of stack below it when the two combine to exceed the container width?
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You could use absolute positioning.
Instead of
use:
and instead of
use:
Be sure to set
position: relative;on your parentdivs so that the absolute positioning is relative to their respective containers instead of the page.