The only way I can think to do it involves a boatload of work on the back end (for you). And believe me, it's gonna suck if you decide to implement it: more likely you'll just say “nah, way too much work”.

The profile I looked at had 39 ribbons. It was the first bio, a fleet admiral or whatever, so I'm guessing he's got most of the possible ribbons. I'll assume just for purposes of my example that there are 42 ribbons. Here's what you'd have to do:

Create a “blank” .jpg - someone with no ribbons at all. Name it:

000000000000000000000000000000000000000000.jpg

Notice there are 42 zeros in the file name. Now, for each possible combination of ribbons, create a new .jpg file that has that particular bit as a 1 instead of a zero, and put the appropriate ribbon in as part of that picture. So for example, someone who has earned just ribbon #6 would use this sig file:

000001000000000000000000000000000000000000.jpg

Someone who had earned ribbons #6, #14, and #41 would use this:

000001000000010000000000000000000000000010.jpg

And so on. I'm not good with math, so I won't even hazard a guess to the number of possible combinations of images there are. It's kinda like the lottery, I'd guess. Lots and lots. BUT... if you only had maybe 20 or 30 guild members, you could build just the images you need “right now” first (and so probably 20 or 30 images right off the bat) and then add them in when you award new medals. Eventually it'd just populate itself.

On the other hand, if you're really clever, you could write a program to create the images for you on the fly using .PHP. I'm not entirely sure how that would be implemented in a sig file though. Or maybe you could just write the program to build all the images for you one time and then be done with it, and then just have your members use the file name convention described above in their sigs.

Did I mention that the effort involved makes this pretty much not worth doing? (The sad thing is, I know that if this was something I needed for my own site, I'd probably do it anyway, even though it's so much work it's not worth doing.)

If it were in a blank HTML box (similar to an embedded page content box) it would be VERY easy to do in PHP. The code would go a little something like this:

<?php
 $medals= $_REQUEST['medals'];

$medalstring = "";
$imagesURL = "http://www.something.com/medals/";
$medalALTtext = array('Medal of Honor', 'Officer Medal', 'Leader Medal', 'Another Medal', 'Get the Idea Yet?');

for($x = 0; $x < strlen($medals); $x++) {
 $this = substr($medals, $x, 1);
 if $this = "1"{
  $medalstring .= "<img src=\"$imagesURL" . "$x" . ".jpg\" alt=\"$medals[$x]\">";
 }
}
  
echo ($medalstring);
?>

To make that work, you'd need to have numbered images (starting with 0.jpg, not 1.jpg) and put them in the appropriate folder on your webspace (the $imagesURL above). You'd put the ALT text for each medal in the array called $medalALTtext. After that, folks would just have to call your .php page with the following URL argument: http://www.something.com/medals.php?medals=01000010100011100001010101. If they drop a 1 in the wrong spot, they'll get the wrong medal, but if they leave some off at the end of the string, they just won't get those medals (it'll be treated as a zero, not a one). For example, someone with the following:

medals.php?medals=01000010

would still get the second and seventh medals, but if there were other medals awarded them that had higher numbers, they wouldn't be displayed. (For that reason, put your most common medals lower in the order; that way, folks with only the first, say, 10 medals or so, could shorten their URL.)

Easy code, but it doesn't necessarily solve your particular problem. Maybe if the signature included your page in an inline frame or something, it might work, but I don't use inline frames so I come up dry offering assistance in that area.