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.

Tom Antarnisti

Antarnisti Smiley for Kaskus adds a collection of smiley shortcodes for Kaskus-style emoticons to WordPress content and comments. It also provides a Classic Editor button and an optional smiley picker below the comment textarea.
This plugin is not affiliated with, endorsed by, sponsored by, or officially connected to Kaskus. Kaskus is a trademark/project name of its respective owner. The name is used only to describe the style and compatibility target of the smiley set.
This 2.5.0 maintenance build changes the plugin name and text domain to a clearer third-party naming pattern, keeps the cleaned-up codebase for newer WordPress versions, and sanitizes the smiley HTML returned by content/comment callbacks.
It also includes an option to disable WordPress native emoji scripts and styles, which is useful when this plugin is used as the site’s primary smiley/emoji system.
Important asset note: this package contains Kaskus-style image assets. Before distributing this plugin publicly, make sure every bundled image asset has a GPL-compatible license or written permission for redistribution under WordPress.org plugin directory rules.

Antarnisti Smiley for Kaskus

Adds an Antarnisti smiley shortcode set for Kaskus-style emoticons to WordPress posts, comments, the Classic Editor, and the comment form.

TinyMCE Smiley Button vs Antarnisti Smiley for Kaskus