Waterdeep’s Movie Moments

Artists Tyler Jacobson and Cynthia Sheppard explain the origins of their Waterdeep covers and why it helps to embrace a touch of the weird at Wizards of the Coast.

Mark Bonington

For many players, the art of Dungeons & Dragons is a portal into the brand. It draws them in, makes turning the pages such a delight and inspires them to keep creating characters and writing new stories. Fond memories of rifling through the Monster Manual or seeing new creatures and environments brought to life in other source books are retained through many a player’s lifetime.

As we celebrate the availability of two adventures set in Waterdeep we chat with Dragon Heist and Dungeon of the Mad Mage cover artists Tyler Jacobson and Cynthia Sheppard about their radical change in style from previously published D&D works.

Designing a Cover

“I wanted to try something a little riskier,” says artist Tyler Jacobson. As the creator of the cover for Waterdeep: Dragon Heist it was his vision that set the template for the connected works, with Magic: The Gathering‘s Art Director Cynthia Sheppard following up with the cover for Waterdeep: Dungeon of the Mad Mage.

Jacobson says his breakaway style for this urban adventure came from a determination that the composition would be something new.

“I really wanted to create something in the style of a movie poster, because the book had the feel of a movie to me,” he says. “So I set out to create a cover that felt like it was for an ’80s film. It’s basically a montage poster and is a style that was made popular by an artist named Drew Struzan, who was famous for his Star Wars work. I asked the D&D team to let me try it, and although it sounded a little crazy they trusted me to pull it off.”

“We worked on one cover each,” explains Cynthia Sheppard. “Tyler planned out the Dragon Heist cover with the beholder in the background and the characters. I was able to start with that. It was like the hardest part had already been solved for me as it came pre-planned! I had my recipe and composition.”

If the movie poster style was a breakaway for D&D, it was also new for the artists themselves. Both Jacobson and Sheppard are far more used to painting story scenes and character figures than montages, which presented its own challenges.

“Things get a little trickier when you create a montage,” Jacobson admits. “You have to figure out how to separate the figures so they don’t appear as if they are in a scene, otherwise the image becomes confusing for the viewer. One way around that is to paint all the characters on a varying scale so they don’t all appear to be in the same place. You can also give each one different lighting.”

Work in progress for Waterdeep: Dragon Heist.

“Keeping things cinematic isn’t how I normally work so it was definitely a challenge to break with my style,” says Sheppard. “I had to keep all of the pieces separate but together, if that makes sense. I blocked out where things sat on Dungeon of the Mad Mage, composing a similar scene to Tyler’s Dragon Heist cover based on the different angles and shapes.

“I was given a bunch of different concept art, along with Tyler’s cover for Dragon Heist. So I had all the pieces to use as a starting point. I wanted them to feel related so I kept the composition but changed the color scheme. I needed Dungeon of the Mad Mage to feel darker and to give the reader that feeling of sinking into an evil dungeon. That’s why I went for the deep red.”

While the composition elements of Dragon Heist were there as a guide, Sheppard had the added challenge of taking on the style of another artist.

“Tyler and I used to do life drawing together,” she explains. “I’ve been a big fan of his for a long time and learning how he works actually really helped me when it came to designing the cover in his style, as many aspects were outside the way that I normally work. But I was able to put myself in his mind-set and create some synergy between the two covers.

“The covers had to feel like a piece of each other. I didn’t want to lose the way that I work but I wanted to bring some of the decision making from Tyler’s work into mine—the lighting, the way the planes of the face work—those sorts of things were me trying to think like Tyler.

“To put yourself into the mind of another artist is both fun and very, very hard. But it does help when you know the person. If I’d never watched Tyler paint it would have been much harder to guess what his decision-making process is and how brush strokes and colors are chosen. We’ve had a good working relationship for a long time and beyond that we’re friends. I think that’s why there’s a good camaraderie between the covers, too.”

Creating Characters

For all their connections, both covers feature a host of different characters players may encounter as they explore Faerûn’s ‘Crown of the North’ and discover the wealth of intrigue and danger above and below its streets. For Jacobson’s Dragon Heist cover, the tribute to Struzan continued in the hooded form of Manshoon, who occupies the prime central space.

“There’s definitely a little bit of a Star Wars hint with him,” smiles Jacobson. “In the initial drawing he had a horrifying face and that’s why it was hidden under the hood, but for the final cover we changed that up to a beautiful face which you can only see a small section of.

“Everyone on the cover is basically a bad guy but they all take different forms in Waterdeep. The Cassalanters are not as obviously evil, which is why I doubled down on making them very beautiful, but they represent the money and wealth of the city. I created them bleeding gold down into the rest of the cover, as if it’s falling out of them. The main focus with them was the masks to show their deviousness and background criminal behavior.

Work in progress for Waterdeep: Dungeon of the Mad Mage

“Jarlaxle is an iconic D&D character so I wanted him dead center, with Xanathar’s eye forming a halo over him. He’s a swashbuckler and the most recognizable with his big feathered hat so I wanted that focus on him visually.

“Xanathar is the in-your-face evil character. Beholders are really fun, you just have to keep count of those eye stalks! I was trying to make sure on the cover that you could see all ten but I think a few were cut off by the end.”

Sheppard reveals that the design of her cover became much more personal than usual.

“What made composing Dungeon of the Mad Mage especially fun was I actually posed for a lot of the characters myself!” she laughs. “I had to liquefy my cheeks to create the githyanki, pull angry faces for Halaster Blackcloak—basically this cover involved making myself into a Halloween mask.

“I modelled all the characters in my studio for positioning and lighting, pushing and pulling to make them more fantastical. The drow female is the closest to the real me. That’s my ‘judgment face’, with different hair and pointy ears.

“Halaster was the character that I concentrated on the most. I really wanted to make him super expressive so a lot of it was about finding exactly where the line is between smiling and crazy—including nasal folds, the arch of the eyebrows and playing with the angles. It’s very important to me to get the details right until the face holds the exact expression I want.

“Everyone was based on some sort of concept art that was sent over but when creating characters I don’t typically start with a look. Instead I try to think of their traits such as their stats and flaws and what job they’re doing. A lot of it comes down to expression. For this cover it was things like making sure Halaster looked crazy enough and making sure the drow looked suitably snotty.

“It’s important to evoke what the characters are about through their facial expressions even if they look otherworldly or post-human. Even the death tyrant gets to have an expression and the placing of the center eye behind the drow’s head carried meaning. Using her head as a fake pupil means it’s staring into the viewer—I love stuff like that.

“The mind flayer and the githyanki are straight from the concept art. They’re not named but are featured there as creatures you could possibly meet when exploring the dungeon.

All about the Process

“As artistic processes go mine is pretty classic,” continues Sheppard. “I typically start with thumbnails. These are sketches to establish basic shapes or narrative composition, echoing the story that they’re going through.

“For example, on the Dungeon of the Mad Mage cover I have two dragons fighting but you can’t show a lot of violence on a cover, so I had the wings intersecting. This means they cut through one another visually, not physically. It’s those little tricks I like to work out at the beginning before adding on the layers.”

“I created it digitally as all my work is digital,” adds Jacobson. “I made small adjustments to give Dragon Heist a textured feel, like those old movie posters that inspired the original design. But it’s something I do with all my work and I always try to push that more traditional look even though I’m painting in Photoshop.

Sketch for Waterdeep: Dragon Heist

“My process is pretty standard too. I’ll get the brief and create a series of sketches. Then I’ll work the ones I like best up to a mid-level black-and-white composition and share them with the art director. They pick the one they like and I’ll finish that one.

“I’ll also work with the writers closely and what I do very much runs alongside the lore development. The writers are really thorough about giving you the feel of a character and any items they have, though I don’t typically go too deep into backstory. I want to hear and see what they feel like in that moment and figure out what the mood of the character is at that particular time.

“I aim for what I call the ‘cool factor’,” Jacobson explains. “Cool is king and there should be a looseness and coolness to the character or the monster. If it looks amazing I like to just go with it.”

Changing the Face of Fantasy Art

Both artists are also united by their desire to change fantasy art for the better. Given the global influence D&D enjoys, they are keen to depict fantasy characters as diverse as the players who inhabit them.

“There was already a movement when I came in three and a half years ago to ‘ban the chainmail bikini’,” recalls Sheppard. “Sometimes, of course, it’s not about simply covering more skin, it’s about thinking on the philosophy of why a character is wearing a certain costume and where it makes sense. I feel like coming from the female perspective I can help educate people on how not to be afraid.”

“I really hate bikini armor,” agrees Jacobson. “Armor functions in a particular way and I’m very much into the practical nature of armor and weapons. It’s a big interest of mine so I don’t like impractical-looking items. All the concept art I’ve done for D&D over the years has leaned that way and I’ve been working with a lot of artists who share that aesthetic.

“I like things to look functional, but even with that fantasy layer on top they still need to have a basis in reality. I think it helps people believe more in the world they’re inhabiting if it is anchored in the functional world. That’s why we also discuss representing more people when we create characters.

“I like to think about how a particular class and character would equip themselves. To me a magic user isn’t going to wear a lot of gear because they rely on their magic abilities but a fighter is going to have a lot more.”

“It’s definitely all about the character,” agrees Sheppard. “What they’d wear, and what the shapes made by the clothing say about them.”

Finishing Touches

For Jacobson, taking the cover art for Dragon Heist and Dungeon of the Mad Mage in a new artistic direction was a creative achievement both for himself and for Wizards of the Coast.

“My favorite thing about these covers is that I was able to achieve that movie-poster look,” he says. “I think it is so appropriate for that campaign. It’s very different from my normal work but I’m really pleased with how it turned out and that they just look so great lined up together.”

“It always helps to have a new opinion on things,” agrees Sheppard. “I would say that to be an artist here at Wizards it helps to have a lot of weird experiences and a new take on things. But that’s why I love it.”

More on Waterdeep: Dragon Heist


More on Waterdeep: Dungeon of the Mad Mage