My own solution is this: 
#<img border="0" src="/images/wink.gif" alt="Wink">

# Match <img, followed by a minimum 38 and a 
# maximum 50 of any characters before reaching
# the specific target word

$body =~ s/<img.{38,50}="Smiley">/:)/g;
$body =~ s/<img.{38,50}="Wink">/;)/g;

[download]
The above code gets me the desired output but I'm not sure if it's the right way to do it. It's overly dependent on the context.

In reply to Re: Why doens't non-greediness work? by kiat
in thread Why doesn't non-greediness work? by kiat

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