Josh

Add over 50 animated smilies to your visual tinymce editor.
This plugin is designed to be used as an add-on to my Ultimate TinyMCE plugin. However, it can also be used as a stand-alone plugin as well.
For best results; You can download Ultimate TinyMCE here: 
https://wordpress.org/extend/plugins/ultimate-tinymce/
This addon will add a button to your visual tinymce editor for posts/pages. Clicking the button will open a popup window with over 50 professionally animated .gif smiley’s.
You can insert these smiley’s into your post/page content areas. Simply click a smiley, and it is automatically inserted into your content area.
<h3>Features</h3>
<ul>
<li>Includes over 50 professionally created animated smiley’s.</li>
<li>Easily insert them into your posts/pages with a single click.</li>
<li>I may consider making new smilies upon request.</li>
</ul>

Moods Addon for Ultimate TinyMCE

Add over 50 animated smilies to your visual tinymce editor.

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.

Moods Addon for Ultimate TinyMCE vs Stylish Smilies