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.

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. :)

Moods Addon for Ultimate TinyMCE vs TinyMCE Smiley Button