Roll20 was originally conceived as a personal project by three college roommates, Riley Dutton, Nolan Jones, and Richard Zayas, to help them continue to play Dungeons & Dragons after graduating and moving to different cities.

[8] Torner wrote, "Roll20 allows players to seamlessly control information in a shared 'tabletop' era and broadcast content of interest to both the group itself and the wider audience watching it play.

Joined with Twitch and YouTube, it constitutes a powerful tool in the kit of industry up-and-comers" and that the "system would impact the play of millions at mass scale [...].

After a failed attempt to get clarification and correction of the ban, ApostleO deleted his Roll20 account and posted a summary to Reddit of the hostile customer-service.

[13] In February 2019, TechCrunch reported that Roll20's databases had been hacked along with those of 8 other companies, with the information of over 4 million users of the site posted for sale on a dark web marketplace.

[15][16][17][18] Liz Schuh, head of publishing and licensing for Dungeons & Dragons, stated that "virtual play rose 86%" in 2020 "aided by online platforms such as Roll20 and Fantasy Grounds".

[19] Erik Mona, for Paizo, commented that "tools like Roll20 and Discord played a huge role in keeping the Pathfinder and Starfinder communities together.

[25] In June 2022, Roll20 announced a new partnership with OneBookShelf that would allow content creators on the Dungeon Masters Guild to sell modules and add-ons which are directly integrated with Roll20's virtual tabletop system.

[40] In addition to the free content, Roll20 also has extra features available for paying subscriber accounts, including dynamic lighting and fog of war for maps.

[44][45] In July 2020,[46] Roll20 released their own science fantasy role-playing game[47][48] named Burn Bryte, with James Introcaso as lead designer.

Jacob Brogan, in a review of Lost Mine of Phandelver on Roll20 for Slate in 2016, commented that "our experience wasn't always seamless at first" and that "all of this data also taxed my computer's resources, crashing my browser outright on at least one occasion.

[35] Ryan Hiller, for GeekDad in 2017, stated that "Roll20 is an industry leading web and tablet based virtual-tabletop application" and that "Roll20 is one of my must have digital tools for roleplaying".

He wrote that Roll20 "is the cheaper, more practical solution for remote D&D: a clean mapping interface, easy access to official reference material, built-in video chat, and quick dice rolls.

[54] Leif Johnson, in a 2020 update on virtual tabletops for PC Gamer, wrote that Roll20 "allows a dizzying range of customization for maps, tokens, and more.

Its menus are a bit drab, but they're intuitive almost to the point of genius, and the package is especially celebrated for its fantastic line-of-sight dynamic lighting system".

[56] Szporn also commented on Roll20's subscription service and stated that the free tier is "the best option for new players but is not recommended for DMs due to its limited access to Roll20's more advanced features".

[56] Luc Tran, in a separate review of various virtual tabletops for CBR, wrote that Roll20 has "a straightforward design tool for maps, dungeons and towns, as well as the ability to create and name multiple simple commands for actions like dice rolling [...].

Unless players choose to purchase specific game compendiums, D&D-specific characters, races, monsters and items will either have to be recreated in Roll20 or you'll have to find suitable replacements".