Cople

TinyMCE Smiley Button

A nice to have would be to turn the text in the wysiwyg to a smiley. EG. :) <- Would turn into the smiley image after a space is added. A client of ours wants this functionality so i shall send relevant code to do so once i've figured it out. :)

Does what it says on the tin.

Stylish Smilies adds CSS classes to text-based emoticons. 
You can then reference these classes in your theme to style each emoticon differently:
<pre><code>.smiley {
/* Applies to all emoticons */
 color: black;
 font-weight: bold;
}

.biggrin {
/* Applies to :D only */
 background: green;
}
</code></pre>
This plugin affects the following smilies:
<pre><code>8-) cool
 8O eek
8-O eek
 :( sad
:-( sad
 :) smile
:-) smile
:-? confused
 :D biggrin
:-D biggrin
 :P razz
:-P razz
 :o surprised
:-o surprised
 :x mad
:-x mad
 :| neutral
:-| neutral
 ;) wink
;-) wink
</code></pre>

Stylish Smilies

Stylish Smilies adds CSS classes to text-based emoticons.

TinyMCE Smiley Button vs Stylish Smilies