Numbers as Circular Graphics
Mathematica - 166 181 bytes

A bit more concise than the other Mathematica answer, thanks in part to a more point-free style.

c = Characters; r = Riffle;
Graphics[r[{0, 0}~Disk~# &amp; /@ Reverse@Accumulate[
    l = {3} ~Join~ r[2 Position[c@"IVXLC", #][[1, 1]] - 1 &amp; /@ 
        c@IntegerString[#, "Roman"], 3]], {White, Black}],
    ImageSize -&gt; 2 Total@l] &amp;


All whitespace is for clarity only. This defines an anonymous function which returns the desired graphic.

Animation



Generating an animated GIF of the number circles is trivial in Mathematica, which has built-in functions for animating and exporting sequences of arbitrary objects. Assuming the above code has just been executed,

Table[Show[%@n, PlotRange -&gt; {{-100, 100}, {-100, 100}}, 
    ImageSize -&gt; 200], {n, 1, 399, 1}];
Export["animcircles.gif", %]


Example Output