Playing the Long Game
Celebrating a pastime that has sparked imaginations and friendships for half a century
Of all the illustrations on the new Dungeons & Dragons stamps, D&D superfan Dante Santos has a favorite, and it depicts neither a dungeon nor a dragon.
This is surprising because Santos, who has been immersed in the iconic role-playing game since high school, has loved fantastical winged beasts for as long as he can remember.
“I was definitely one of those kids who — when I went to the bookshop as a 12-year-old — my criterion for what book I was going to get was ‘How big is the dragon on the cover?’” he says.
Santos still relishes the chance to lose himself in elaborate fantasy worlds, and today, he gets paid to do it. As a professional Dungeon Master, or DM, Santos makes a living running Dungeons & Dragons games, which means that he guides groups of five or six people on richly imagined adventures.
“The highest number of active games I’ve had going concurrently is 11,” he says. “It's a bit like trying to write 11 fantasy novels at the same time. People always ask me, ‘How do you keep all of the campaigns straight?’”
He can answer that question easily. “It helps that I was a professional project manager before I started doing this,” explains Santos, a former engineering team lead for Microsoft. “I'm really good at spreadsheets and notes.”
Since its creation in 1974, D&D has changed perceptions of what tabletop gaming looks like. The players rely on maps (either pre-generated or ones they draw themselves), sets of polyhedral dice, a rich trove of related literature, and their own imaginations. Some games are one-offs, while others, known as campaigns, can go on for years or even decades.
Each player is responsible for developing their particular character and acting as that persona might, whether they’re “engaging in high espionage or fighting goblins or studying wizardly magics,” Santos says.
DMs like Santos oversee the whole experience, describing the setting, inventing obstacles for the players, and playing the roles of other people that the party encounters.
“The DM is really there to facilitate the story that’s being told,” Santos says. “They’re the custodian of the world.”
His passion for crafting and maintaining fantasy realms also explains his favorite design among the new stamps: the purple worm.
In Dungeons & Dragons, these massive, eyeless monsters burrow through the earth, leaving colossal tunnels in their wake. Although Santos can’t pretend to boast a gaping mouth of knife-like teeth, he feels an affinity with the creatures.
“They are environment shapers,” he says. “In their own way, they’re world builders. And they’re very fun to incorporate into a [D&D] encounter.”
Not just a game
Greg Breeding, who art directed the Dungeons & Dragons stamps, notes that Santos is not alone in his appreciation for the purple worm.
“He’s a very iconic monster and one that fans really gravitate to,” Breeding says. “I was sure to make room for him.”
Breeding has overseen a range of otherworldly postal projects, including the Dragons stamps that were released in 2018, as well as stamps issued in 2013 and 2021 that featured Harry Potter characters and droids from Star Wars, respectively.
Knowing that science fiction and fantasy subjects often speak their own cultural and visual language, Breeding prepared for art directing the stamps by interviewing fans, exploring relevant YouTube videos, and poring over nine core books that serve as references for players.
What he discovered in the process charmed him. “I was delighted by the sense of community, the collaborative spirit, the exploration of mythology — all of that is what's in the foreground,” he says.
The social aspect of Dungeons & Dragons is a big draw for Santos as well. Recalling countless weekends of gaming in high school, he remembers how newcomers and members of other groups joining a game often inspired lasting real-world friendships.
“One of the age-old tropes in the genre of fantasy is found family,” Santos says. “Many of the characters’ stories in D&D are about that, and it parallels the experience that many players have [through the game].”
Santos has experienced this himself. In 2019, he started running a campaign online with players who had never met. Four years later, they’ve all become close friends and plan to rent a beach house together this summer, when they will meet in person for the first time.
After all of the research he completed to create the stamps, Breeding says he can imagine what it must be like to spend years bonding with others through D&D.
“It’s your people, your characters — it must be nice to have that kind of history with each other,” he says. “It must feel like home.”
Snippets of story
Although danger and excitement characterize many of the events in D&D games, Breeding wanted the stamps to reflect a fitting sense of warmth and community as well. He and the postal art team lightened the illustrations they used, which were taken from past and current D&D books. This not only resulted in clearer pictures, but it also turned up the volume on the vibrant colors.
To convey the game’s dynamic storytelling, Breeding made sure that the stamps depicted intriguing snippets of scenes. A traveler stands at the center of a maze spell, a fiery-haired woman bathes in dragon’s blood, and on the stamp selvage, a band of adventurers stands ready to battle the roaring dragon before them. Taken together, the stamps feel like tiny postcards from another realm.
They absolutely capture that high fantasy, that sense of adventure.
Breeding hopes that the stamps will remind people of the power of stories. “As a grandfather, I know my grandchildren love books. They love stories.” he says. “If the D&D stamps serve to encourage and popularize storytelling, that would be delightful to me.”
The Postal Service has timed the release of the stamps to celebrate the game’s 50th anniversary, and the D&D community sees them as a welcome sign that “we’ve reached the mainstream,” Santos says.
When he looks at the stamps, Santos remembers the thrill of being a kid about to discover D&D — a kid on the hunt for the best dragon-themed book he could find.
“They absolutely capture that high fantasy, that sense of adventure,” he says. “The selection of imagery across the board is absolutely perfect for people like my 12-year-old self.”