It can be hard to remember how primitive the internet landscape was in the late ‘90s, the era when webcomics came of age. The only way to share things was through email and instant message, and a seconds-long video clip could crash email servers if too many people sent it around. Something Awful was still a “weblog.” We went to websites — plural — to check for updates every day.

Webcomics creators often went online after being rejected by newspaper syndicates, gatekeeper conglomerates that grew increasingly conservative in the ‘80s and ‘90s. The best ones grew into beloved phenomenons, and the nascent funny T-shirt industry allowed many artists to make a living on daily cartoons throughout the 2000s.

Social media and a glut of internet merchandise have shifted the economics. Artists increasingly rely on Patreon, book sales, and other sources of revenue, while new webcomics often pop up exclusively on Instagram, foregoing the expense of a dedicated site. But in those early days, webcomics were some of the most influential pieces of the early-ish internet — vibrant and weird. They formed followings, which became communities, which became culture.

We asked those artists to tell us all about living through it.

“My early comics just sort of belonged to the internet.”

Jon Rosenberg, Goats and Scenes from a Multiverse: I started putting my comics online in April 1997 when I got 5MB of server space with my dial-up account. There wasn’t anything on the internet. Even if your comics were complete shit — which mine were — there was an expectation that people would look at them. What else were you going to look at?

It was also a way to get around newspaper syndicates. Most of the packets I sent to them got rejected out of hand, but I got one letter back from a big editor, Jay Kennedy [of King Features Syndicate]. I’ve got it up on my wall. He said mixing animals and humans in the cast was confusing.

All of the comics that inspired me to become a cartoonist mixed humans and animals. It just revealed to me what bullshit it all was, that syndication wasn’t something I needed or wanted to pursue.

Kris Straub, Checkerboard Nightmare, Chainsawsuit, Starslip Crisis, and Broodhollow: In the late ‘90s and early 2000s, instead of trying to expand audiences, syndicates were trying to maintain a grip on the audience they did have. We’re going to have Marmaduke forever. We’re going to have Heathcliff forever. We said, “Alright, we’re just gonna go online.”

“We were all kind of humbly in awe that people were even reading our work.”

My first webcomic was called Checkerboard Nightmare. It was very meta. I noticed every comic’s first couple of strips were just their characters standing around going, “I guess we’re in a comic now. What do we do?” I started poking fun at those tropes.

Jeffrey Rowland, Wigu, Overcompensating, and merchandising company TopatoCo: Somewhere around 1998, I looked at Dilbert and thought, “Anyone can do that.” After about 35 rejection letters from syndicates, I started putting comics online. In a few months, I realized there were 1,000 people a day reading this comic. This was in a GeoCities site before I even got my own hosting.

All of us started communicating very early on, bouncing ideas off each other. I probably talked with John Allison of Scary Go Round for two or three hours a day while I was at work. We came up with the character Topato, who TopatoCo is named after, in an AOL instant messenger conversation: “What about a superhero potato?” “Oh yeah, what if he had a pony sidekick?”

Meredith Gran, Octopus Pie, adventure game Perfect Tides, and professor of comics at the School of Visual Arts: I started reading webcomics around 1999 when I was 15 or 16. I did a few stop / start comic attempts in high school and college. My first comic was a furry high school romance. The world wasn’t ready for it yet.

I was really into the Keenspot community, which combined forums and free hosting for webcomics. It was run by Chris Crosby, who did Superosity. By the time I started Octopus Pie, I already had a lot of friends in webcomics who were chomping at the bit to link to my work.

It’s crazy to think how much work it was, doing a daily strip. Everyone had this mindset that you had to do it just like a syndicated strip, you had to be putting it out on a regular update schedule or everyone would forget about you. We were all kind of humbly in awe that people were even reading our work.

Rosenberg: Until around 2000, the way people found new webcomics was a site called Big Panda. They had the first top webcomics ranking list, probably. Anybody with a comic, we were all scrambling for the top of this tiny hill.

Ryan North, Dinosaur Comics: Top lists were kind of like traffic Ponzi schemes. You’d put a link on your comic that said: “Click here to vote for me,” sending people to their page. In exchange for clicks, you got to the top of their list. It felt very performative, so I stopped doing it.

“I guess the way I got early readers was… vandalism?”

The first comic I read was Achewood, which is probably the best webcomic ever. It didn’t have a links page, so I thought Achewood invented webcomics. Mine was the second webcomic on the internet.

I was in a college entrepreneurship class, and a month into a group project, our group hadn’t done anything, so I just decided to put comics online.

I cut little T. rex silhouettes out of construction paper and put them up around campus with the URL on them. I’m very tall, so I could jump and get them up where the janitorial staff couldn’t reach. When I heard people in the cafeteria talking about Dinosaur Comics, I thought I was being pranked. I guess the way I got early readers was… vandalism?

Dinosaur Comics went up February 1st, 2003. Within a week, I got an email from Joey Comeau of A Softer World. He was like, “I do a comic, too. Here’s a link!” I thought, “Wow, there are three comics on the internet.”

Randall Munroe, XKCD: When I started in 2006, the dynamics of “going viral” were there, but we didn’t have words for it. I posted a few comics on my site and shared a link with a few friends. Somebody messaged me on AIM, “I sent this to a guy I know who runs this site Boing Boing. He might do a post about it.” My site was hosted on a Pentium 1 at my mom’s house, so I had to scramble to find hosting that wouldn’t collapse when more than 10 people tried to visit.

Dylan Meconis, Bite Me and Outfoxed, among many others: In the beginning, a lot of guys with strips had dedicated websites and huge audiences. Those of us doing longform, character-driven stories were all on LiveJournal and a few forums, passing our graphic novels hand to hand. I went to high school with Erika Moen of DAR and Oh Joy, Sex Toy, who introduced me to Studio Forum. It was a very female-slanted community. That’s where I posted the first pages of my first comic, Bite Me.

“There weren’t a whole lot of teen girls wandering around San Diego with original work.”

It was run by an animator named Aimee Major. I wish I could send Aimee some bricks of solid gold because she invested so much time and energy into community moderation. It’s way harder to keep kids safe now. You can’t moderate Twitter.

A couple of us formed a little collective called Pants Press to pool our resources and readership. We went to San Diego Comic-Con with a photocopied mini-anthology to give out. We got a lot of attention — there weren’t a whole lot of teen girls wandering around San Diego with original work. People were happy to see us, but also confused, like maybe they were being Punk’d.

Nicholas Gurewitch, The Perry Bible Fellowship:

My early comics just sort of belonged to the internet. I had made the decision not to clutter them with my signature or branding. I might regret that now. At one point, the Perry Bible Fellowship website was in the top 100 or 200 websites on the internet. I was mostly anonymous. It was the most obscure notoriety anyone can experience.

“It turned out, people loved buying funny T-shirts.”

Rich Stevens, Diesel Sweeties: It was actually possible to grasp the webcomics landscape at one point. The first people I met were Jeffrey Roland and John Allison. We decided we were going to go to San Diego Comic-Con in 2001 because Johnny had wanted to go since he was a kid.

The next year, we got a small booth. Some of us had a message board called Dumbrella, which is still the name we use at Comic-Con. Everybody should give me a pat on the back for deleting the Dumbrella forum completely because I’m sure I saved a lot of people’s careers.

Rosenberg: Around 2002, I had been talking to a bunch of guys who were all going to Comic-Con, and I said, “Hey, what if we all shared a table?” They said, “Sure — we’ve kind of been calling ourselves ‘Dumbrella.’ Why don’t you be part of that?”

“We all were very insecure and didn’t know what we were doing.”

That provided a support network for me that, still to this day, helps me. We all had a modicum of talent, but we all were very insecure and didn’t know what we were doing. To have each other’s backs like that gave us the courage to go forward with something that otherwise would have probably been a hobby.

Meconis: We were all trying to find ways to spread interesting work in an affordable way for artists. Hosting a popular comic was really expensive. If somebody important linked to your comic, you were looking at $400 in server fees.

Joey Manley, who passed away way too young, created Modern Tales in 2002, which was a network of subscription anthology sites. You’d pay a monthly fee for access to the archives. Some Pants Pressers had comics on Girlamatic, which was aimed at women in fandom. It wasn’t exactly a wild success, but it paid for most of my rent fresh out of college, so I’m eternally grateful.

Jeph Jacques, Questionable Content: Rich Stevens was the first guy to figure out a reliable way to make money off a comic he was giving away for free on the internet, and the rest of us just followed his lead for the first couple of years. It turned out, people loved buying funny T-shirts, so that underwrote all of our comics for most of the early 2000s.

Stevens: When I first figured out we could sell shirts with PayPal, I went to Kurt Brunetto, who owned my local comics shop in Connecticut. People called him “the T-shirt guy.”

Rowland: Rich Stevens was like, “Hey, I made this T-shirt and sold a bunch, you should try it.” There wasn’t very much competition back then, so it was pretty easy to sell a T-shirt.

“He went from printing T-shirts in his basement to renting a place in an industrial park.”

I started taking T-shirt orders for other artists. They would sell shirts on their site and forward the order emails to me, and I’d get them made and mail them. That was the start of TopatoCo.

I switched to buying shirts from Brunetto, and he scaled up alongside us. He went from printing T-shirts in his basement to renting a place in an industrial park.

North: Merch used to be more personal. When I first put up stickers on my website, this one woman in DC ordered a single sticker for like $2, so I sent her 10 stickers and a letter that said: “Thank you so much, I’m so excited!”

To keep up my fabulous grad student lifestyle, I had to sell three shirts a day through TopatoCo. I was making $5 or $6 a shirt. One time, I didn’t sell any shirts all weekend. I emailed my friends like, “What’s happening, am I done?” Then I sold six shirts on Monday.

Rowland: In 2004, I got bit by a spider — if you search Wikipedia for necrosis, you see a picture of my leg. I missed a lot of work because I couldn’t walk, and got laid off. When George Bush got reelected, I made this T-shirt, the Flabbergasted Eagle, which sold 1,000 shirts in a month. I decided to give it a shot full-time. Being close to death makes you a little nihilistic.

I moved from Oklahoma to Easthampton, Massachusetts, around where Rich and Jeph lived. Meredith Gran and a couple of other people moved, too. It felt like a good place to start a commune, even though we were all basically computer hermits.

I would drive back and forth between Massachusetts and Connecticut in my little Acura, with roof racks so I could put boxes of shirts on top of the car.

“We were all stupid and young, just learning to be people.”

Stevens: I needed to get the hell out of Connecticut, and I heard about this old button factory called Eastworks in Easthampton, Massachusetts. I went to see an apartment there, and had a lease about four days later. Jeffrey drove out and lived in my walk-in closet until he found his own place.

Gran: Doing comics can be really isolating, so there was a lot of drinking and commiserating. In 2009, we convinced the Eastworks owners to let us open up the whole space for an event called New England Webcomics Weekend. We had exhibitors, a concert, art galleries, a video arcade — we flooded this tiny town.

Jacques: Every year, TopatoCo rented a big house for San Diego Comic-Con. They called it Party Mansion. We’d be hanging out in this big rented mansion talking about video games with Pen Ward, before he made Adventure Time, and Jhonen Vasquez, who created Invader Zim and Johnny the Homicidal Maniac.

Rosenberg: In San Diego, me and the Dumbrella guys would always go to this very fancy Art Deco hotel with a little piano bar. We made friends with this tiny bartender named Alfred. He taught us everything he knew about scotch. It became legendary.

“We were a bunch of nerds feeling power for the first time.”

One year, 60 cartoonists showed up. We were hanging out drinking, and realized Jonathan Frakes, Riker from Star Trek, and Avery Brooks, who played Sisko, were sitting in a corner — basically Star Trek royalty. Riker went to the piano and sang show tunes for an hour and a half. When he was done, Sisko went up and started doing jazz, getting progressively drunker until they shut the bar down.

Jacques: I’ll never forget that. It was just an entire bar packed full of webcomics people, watching in dead silence while drunk-as-shit Star Trek captains sang show tunes all night.

Rosenberg: The webcomics community was still very small, and I think we were some of the best-known people in it. We were a bunch of nerds feeling power for the first time. It was fun for a few years.

There was a lot of drinking in those days. It wasn’t healthy for me. We were all stupid and young, just learning to be people. I watched a lot of friends wise up, or they didn’t learn, and completely destroyed their lives. It’s a bittersweet time to think about.

Stevens: The golden age of people socializing in Easthampton was maybe a five- or six-year window. A lot of us came up here. When you’re doing things alone in the dark, it’s nice to know someone else is in town. That lasted for a while, and then we all kind of drifted.

“That lasted for a while, and then we all kind of drifted.”

We were always a separate community from gamer comics like Penny Arcade, but you’d get to know people at Comic-Con. Over time, they got more tone-deaf. In 2010, Penny Arcade ran a comic where the punchline was about being “raped to sleep by the dickwolves.” It bothered people.

They could have apologized, or just said, “I’m not going to apologize, see you tomorrow with a new joke.” Instead, they doubled down and produced shirts that said “DICKWOLVES,” to defy the people who were trying to censor them.

Rosenberg: We were always aware we had found a way to express our views and say things directly to a massive audience. But as Spidey says, you can’t just have the power. You need to take responsibility, too.

Nothing against the Penny Arcade creators, but I always got a proto-GamerGate feeling from their audience. Their fans seemed like a very hostile, resentful group of people.

North: If you do something bad and apologize — which I feel like the Penny Arcade guys have — what do you do next? If you leave it up, new people will keep rediscovering it. If you take something down, people will spread it around like, “This is the secret opinion they’re trying to hide.”

GamerGate came from a toxic culture and horrible people, and some of those people read gamer webcomics. But finding other people who are resentful in the same way you are is more a social media thing than it is webcomics.

“The internet has fundamentally changed.”

Straub: In 2008, three friends and I wrote a book called How to Make Webcomics. It was dated as soon as it came out — Twitter isn’t even in the book. People would say, “I read your book, I’ve been doing a comic for six months, and nobody’s reading it.”

Matt Lubchansky, Please Listen to Me and associate editor at The Nib: Kris Straub’s book felt like, “Ah-ha, a shortcut!” But by the time I started doing comics full-time in 2014, I didn’t have any illusions that I would pay my bills writing webcomics and selling T-shirts.

I kept working other jobs until the fall of 2013 when Matt Bors at The Nib contacted me to reprint a strip of mine that had gone moderately viral-ish on Twitter, and then hired me.

Rowland: Now that everyone is online constantly, the market is so saturated. And especially with Patreon, the model for monetizing your creativity has shifted away from merchandise. TopatoCo used to front book runs, and now you just do Kickstarter. Things have changed so much. We’re trying to change with them, but it’s hard.

North: I used to run an ad network, Project Wonderful. We had around 10,000 publishers around the peak, maybe 5,000 or 6,000 webcomics, and about 10 times that many advertisers.

“It can be really hard to build a fan base when people only see viral stuff.”

It shut down last year. The internet has fundamentally changed. People experience media through Facebook and Twitter now, instead of going to websites. It can be really hard to build a fan base when people only see viral stuff.

Gran: I make my students buy a web host and a domain name and build it with HTML, from scratch. The companies that create platforms get bought and sold nonstop. You can’t be beholden to them. When things fall apart, you’d better be resourceful enough to handle the next thing.

Zach Weinersmith, Saturday Morning Breakfast Cereal: I’ve been saved repeatedly by other webcomics. In 2007, an ad company booted a lot of comics off their platform. My income fell by 70 percent. I was 26, I didn’t have savings. I messaged Chris Hallbeck [creator of Maximumble] in a panic. He said, “I’m going to tell you exactly who you need to talk to.” Within a couple of months, I was back on my feet. I don’t know how I would have gotten through it without him.

Somehow it all worked out. I went from barely being able to pay my rent to having a very nice career. My most recent project is a nonfiction graphic novel, co-authored with an economist, proposing an open framework for immigration.

Straub: My income stream is pretty varied now. I was doing intro animations for a live Dungeons & Dragons game for the Penny Arcade crew, now I play a weekly D&D game on their Twitch channel. I still have webcomics that I update slowly.

Patreon is great. My audience has gotten older along with me. They know if they buy a $20 shirt, I get $8 and they get a shirt they don’t need. They’d rather just give me $20.

“We’re all very nervous about Patreon messing something up because it’s been such a game-changer.”

Munroe: People get XKCD in all kinds of ways now, like Twitter bots and Facebook. I also do a couple of other things that let me reach people who would never come across my website. I have two books, Thing Explainer and What If, and this September I have a new one, How To, coming out.

Meconis: A lot of people from Studio Forum have books out with traditional publishers, or work for animation companies. I’ve got books coming out with both comics and traditional publishers, I’ve got Patreon, I do consulting for giant corporations. I like diverse challenges and diverse income streams. We’re all very nervous about Patreon messing something up because it’s been such a game-changer.

Nothing I’ve ever put online has been massively popular, but it’s been very beloved by its weirdo niche. There are folks who have been following me for literally fifteen years. We all pack our bags together and go wherever we need to.

Rosenberg: It’s always been about trying to make the art you want to make, instead of the art someone bigger or more powerful will let you make. The one constant on the internet is change — a model lasts for a few years, and then you have to go find a new one. You have to be willing to give everything up when the paradigm shifts.