My preferred method for doing this takes some setup, but displays much nicer than doing it via rollable table would. Additionally, rollable tables can't display images when rolled inline. So here's my preferred method (which I really need to add to Keith's Stupid Tricks Thread): Upload your images somewhere that the image can be accessed via a direct link. The Roll20 Library (although difficult to work with), imgur, or something similar. Next we need a link shortening site that allows custom names. Tinyurl or bit.do as examples I'm going to use these four images: 1 2 3 4 . The short url for which is <a href="http://tiny.cc/image_swap_demo_#" rel="nofollow">http://tiny.cc/image_swap_demo_#</a> Then make your macro: [Image[[](<a href="http://tiny.cc/image_swap_demo_[[1d4]]#.gif" rel="nofollow">http://tiny.cc/image_swap_demo_[[1d4]]#.gif</a>) The double open brackets in the image title (i.e. [image [[ ]) are there to force the dice roll to display as plain text so that the link works correctly. This will give you an image based on your die roll: *Images are from Paizo's Starfinder rule books (Alien Archive and Pact Worlds). Used for demonstration purposes only. Paizo retains all rights I've done it with .png's here, but it works with .gifs as well (and in fact, you can see that is what I used as the file type extension in the link (i.e. #.gif). As an added bonus, this method means that you just need to copy your macro between games instead of having to deal with recreating a rollable table in the new game, or having to ask your GM to setup a rollable table for you.