Hi Greg! I might PM you, to offer to run some Roll20 tabletop experiments with you and try to achieve somethin' so look for incoming message if you want to dig deeper on this. There is not currently such a Font in the roll20 VTT text-tool. There is not any sort of Symbol or Dingbat or Webdings font in there yet. They did radically expand the font-list a few months ago, from around 4 choices to around 12+. This shows that certainly Roll20 could consider adding more Fonts there. Good news workaround, type Emoji using your OS. They usually work (in many areas of Roll20 including Text Tool). Modern computers with Mac or Windows usually allow access to an Emoji panel via your keyboard, so find out what button or button-combo opens your Emoji choices and try typing some of those. They look pretty cool when you upside the Text to size 100 or higher. They look about the same regardless of which text-tool Font is enabled. If you are satisfied with the cartoony modern glossy appearance and symbols selection. Your Players can access/type emoji in the same way. Roll20 Marketplace art-pack objects... There are some verrrry cool Map Marker, cartography, icon sets in the Marketplace. An incredible series that might fit your bill is the artist Russ Hapke's line of Old World map objects. This is OSR feel while being much-much-more beautiful and sophisticated and flexible than any Font method could ever be. Once you Purchase 1 or more of these packs (around $5) they are super easy to drag-drop onto Roll20 maps as GM. It would take a bit more work to set them up for access by the players. Check this collection out: <a href="https://marketplace.roll20.net/browse/publisher/49/russ-hapke" rel="nofollow">https://marketplace.roll20.net/browse/publisher/49/russ-hapke</a> Advanced Dice... another quick trick, if you roll some dice let's say roll 6d6 in chat. Drag-drop the dice icons from the chat onto the tabletop. Those become free icons, of very generic numbered nature. Your players can do this as well as GM as long as 'advanced dice' is enabled in the game table settings.