TL;DR: I recently wrapped up a seven-year-long D&D campaign, and wanted to share some thoughts and favorite moments.
Like a lot of people, I got into D&D because of a liveplay podcast. Specifically, the first liveplay podcast, Acquisitions Incorporated, which not only kickstarted an entirely new genre of entertainment but also remained a juggernaut in the field. Anyone who wasn’t there when it started may be unaware that it began pretty humbly — Wizards of the Coast reached out to the Penny Arcade guys in 2008 to ask if they’d be interested in recording a gameplay session to help promote the upcoming release of the fourth edition of D&D.
The original team was just three players — Mike and Jerry from Penny Arcade and their friend Scott from PvP — and now legendary DM Chris Perkins. Their mix of experience with the game was perfect for promoting a new edition. Mike had never played any D&D before, while Scott and Jerry had some experience under their belts. As a result, Perkins could explain the game for newbies when talking to Mike, and get into the nitty-gritty of the changes for fourth edition when talking to Jerry and Scott. It helped that the three players were extremely funny, and used to riffing together to come up with webcomics.
I was hooked, and immediately bought the starter set, and by April 2009, I had roped some friends into playing a game, with me DMing. That group met infrequently, and over the next few years, I joined some games as a player, attended some pickup games at conventions, and DM’d for several groups of coworkers across a few companies.
But the longest stint started when I joined Say Media. In September of 2015, I put out word that I was interested in starting a D&D group, and invited anyone interested to join us. No commitment, and no need to know the rules, just show up ready to have fun. I ran a group of 5-10 coworkers through a Tomb of Horrors-style adventure. We all had a good time, and I put a recurring event on the calendar: Every other Wednesday after work, anyone who wants to join is welcome, I’ll run the game as long as there are at least three players.
Over the next few years, people drifted in and out, but the core of the group stayed together, continuing to meet every other week even after I lost my job at Say. We’d meet up at whoever’s office was convenient and had a conference room to use.
When Covid hit, we kept playing remotely. It took a while to adjust to playing over Zoom, but we made it work. There are fewer fun opportunities for excited cross-talk, but it’s also a lot easier to follow what’s going on with mostly only one person speaking at a time.
At first, I was just running pre-published adventures for the group. A mix of whatever I could find that sounded fun. At times, I would come up with my own stuff, but I had a tendency to fall back on Adventurers League modules because they were quick and easy to run without much prep work.
My group continually astonished me. One time we were playing in the city of Mulmaster, a canonically horrible place, and to be perfectly honest, my group wasn’t loving it. The vibe was wrong. I had a suspicion something needed to change when to prep for a heist, one player got a job as a security guard and spent some time wondering why he would ever go back to the heist rather than keeping the steady paycheck and low-stress guard job. The heist went off well, but soon after they were having a hard time chasing a fire-worshipping cultist who was starting a conflagration when one player said “Fuck it. I think we should leave.” And then the group GOT ON A BOAT and LEFT THE CITY. I had to scramble a bit and ended the session early.
When they came back next time, I announced that some time had passed, they’d sailed to the city of Neverwinter and were looking at wanted posters with their faces — since they’d fled the scene of the crime, they’d been blamed for the terrible fire that burned a huge portion of Mulmaster. The group spent some time clearing their name, but eventually named themselves the Mulmaster County Volunteer Fire Department in a cheeky nod to the event.
One time, I decided that we’d done plenty of dungeons, but hadn’t actually met any dragons. I spent several games leading them towards a confrontation with a dragon. This was going to be a big fight, but I thought they could handle it. The story evolved organically. If a player said something funny or clever, I’d work it in.
By the time they arrived at the dragon’s lair, we’d established that the dragon’s crew of cultists had been kidnapping bards across the land, forcing them to learn new songs to convince more people to worship the dragon. The group broke in, freed the bards, and went to confront the dragon — who by this point had been established as an aspiring rapper. Then, rather than fight with weapons, they challenged the dragon to a rap battle.
There are no rules in D&D for a rap battle. Trust me, I looked.
I had to improvise a series of contested performance challenges. The group aced it. It wasn’t even close. In-game, they soundly defeated the dragon — then they offered to represent him as agents. From then on, my challenge as a DM was to find creative ways to allow them to “book a show” to summon the dragon that didn’t just amount to handing them the ability to call in an air strike. Eventually, the dragon figured out they weren’t getting him good gigs and fired them.
Over time, the group got a bit too raucous. One player collected trophies. Another thought that was a good idea, and started collecting mementos from defeated enemies. A branch from a treant. The mechanical arm from a robotic construct. Over time, without fully considering it, the running joke had become the rather grisly practice of peeling the faces of the dead.
One night, a new player joined our group. Someone we didn’t know in person, but I had met at a tech meetup. She started out enthusiastic to play with us and left the evening clearly horrified after watching the group burn an enemy alive, peel his face, and then commit a bit of light genocide against a group of modrons.
It was a wake-up call. I remember talking to Chuck about how upset she was and how awful I felt that she had a bad time. These were all just jokes that had started small but had somehow grown into horrifying proportions. Chuck helped me realize that my discomfort had more to do with myself and realizing that I wasn’t running the kind of game I wanted to run anymore. I don’t need my players to be exemplars of justice and moral fortitude — but somehow we’d stopped even trying to be the good guys.
Around this time Chuck also became a much bigger part of the story. He’d joined the group as a player a few times, but it never really clicked for him. But he loved hearing me tell him about what the group got up during the games, and acting as a sounding board for my ideas. Eventually, I realized that Chuck was more than just a silent partner, he’d become a co-DM, and I started referring to him that way. Some of the best ideas in the campaign came from riffing with Chuck, each of us helping to knock the sharp edges off rough new ideas and refine them down to something approaching a plan.
What came out of our conversation was an adventure my players fondly (I hope) refer to as “the morality arc.” I had them be kidnapped into a dystopian future by a version of the History Channel and had them compete in a reality show gladiator program forcing the worst criminals from across history to fight to the death. That’s how they learned that they were regarded by the future as notorious villains. (I came up with a mini-game to generate a Wikipedia page that I’m still quite proud of.) In the end, the players returned to their own timeline, with a little in-game nudge to try to leave the world better than they found it. (Don’t worry, I also had a frank conversation with them about what I wanted to keep the game fun moving forward, and they were all on board.)
What followed was me and Chuck creating a campaign structure where the group worked for a secret organization whose explicit aim was to make the world a better place. As operatives, they had a free hand to pursue this goal as they saw fit, but they would receive bonuses for non-lethal solutions.
That was November 2018. What followed was four years of a single campaign of mostly published one-off adventures united by an overarching plot involving the group they worked for, the big bad the group was opposed to, and a surprisingly complicated political backstory, mostly guided by what my players responded well to.
The finale of that campaign happened in February 2022. It played out over three sessions and resulted in finally paying off an idea I’d been seeding and teasing for literally years, a goddamn set of Voltron armor the group had to use to fight an elder god in the form of an ancient dragon. It was so much fun, and loaded with fan-service-y callbacks to earlier encounters and characters they’d met over the years.
We’ve since started a new campaign, that I’m having a lot of fun with, but I will never forget the time I spent with this group, especially the longest-running characters.
- Averlyth Cai, the drow cleric of Bane, who spent a great deal of time spreading the good word of a terrifying god, and who ended the campaign riding around in a pimped-out coffin on spider legs.
- Kanye Cantaliber Esq., the half-orc battle master who never met a door he didn’t kick open, carried a scroll of pedigree and always announced himself before a fight (to give his opponent a chance to flee).
- Nissa Atlock, the gnome bard who spent the vast majority of her time slinging insults from the safety of Kanye’s shoulders and looking for new libraries to spend time in.
- Quinumum Ebraldeth, aka “Um,” the halfling rogue who acquired a set of slippers of spider climbing, and spent every fight from that point forward as a sniper hanging from the ceiling like a bat.
- Sorith, the dwarf monk, whose love of brewing was matched only by his distaste for other dwarves.
- And of course, Carlos Blöodfarte, the half-elf sorcerer whose unlucky roll on a wild magic surge chart left him with a very long neck for the rest of the campaign.
I love them all like children and have threatened/promised my players to bring their characters back as NPCs in an adventure I may publish someday.
When we used to play in the office, my boss would knock on the door and teasingly ask “Who’s winning?” And I would always tell him: “Me! I’m winning, because I somehow convinced my friends to show up every other week to tell me stories and make me laugh.”