Comic books are, in many ways, one of the most low-tech forms of entertainment — just ink on paper. But, like literally everything in our society, the internet transformed them. Instead of having to pay thousands for a print job or go through one of a few publishing companies, aspiring cartoonists can now reach a massive audience just by scanning and posting their work online. Enter webcomics, which have proved to be a launching pad for globally famous talent, a way to advance the art form and a fine way to make a living.

This is a chronological list of the 16 webcomics that exerted the most influence over the medium, both creatively and commercially. Reading it, you can see how webcomics have grown in scope and ambition, from early imitations of existing forms to completely new content experiences. What does the future hold for comics online? Follow the path and maybe you’ll get some ideas.

Witches In Stitches

Let’s start at the very beginning: Before the World Wide Web stitched together the Internet as we know it, online communities congregated in a variety of walled gardens like AOL, Prodigy and CompuServe. In 1985, a Detroit artist named Eric Millikin uploaded a parody of The Wizard of Oz called Witches In Stitches to that service. This was before the Mosaic browser allowed inline images, so to read the strip people had to download it to their personal PC. It quickly inspired other artists to share their work online as well. Copyright claims forced Compuserve into taking the strip down, and no visual record of it remains online today. Millikin has continued to make artwork digitally for several decades and won a Pulitzer Prize in 2009.

User Friendly

The early audience for the World Wide Web was tech-savvy geeks, so appealing to them was a smart choice. J. D. Frazer, who drew under the alias “Iliad,” launched User Friendly in 1997 and it quickly became a favorite among the extremely online tech support staff that had Internet access. Chronicling the trials and tribulations of a fictional Internet service provider, User Friendly’s form and content weren’t far off from your average daily newspaper strip. But Frazer’s keen knowledge of real technology gave it the ring of truth that it needed to draw an audience big enough to pay his bills. He continued to draw new strips daily until 2009, when it went on indefinite hiatus.

Penny Arcade

Comics have historically been dominated by genres – funny animals and superheroes are two of the most enduring in the American industry. But in the burgeoning online culture of the late 1990s, creators had to choose a subject matter that resonated with the predominantly young and male userbase. For Mike Krahulik and Jerry Holkins, that subject matter was video games, and it made Penny Arcade one of the most successful webcomics of all time. The simple format – typically three panels, commenting on gaming culture and news of the day with a punchline at the end – coupled with a robust discussion thread underneath – laid the foundation for thousands of imitators, none of whom had the longevity of “Gabe” and “Tycho.” The growth of their empire to include video games and even an international series of conventions is testament to how solidly they established their niche.

Megatokyo

One of the most important trends in the last few decades of comics is the influence of Japanese comics and cartoons on Western artists. Fred Gallagher and Rodney Caston’s Megatokyo debuted in 2000 and was one of the earliest examples. Starting out as an otaku-focused gag strip, after Caston left the partnership Gallagher transformed it into a serialized homage to the shoujo manga that he loves – missed connections, awkward romances and unusual supporting characters combine with glacial pacing to make a read that’s not for everybody but popularized the style online.

Bob And George

The democratizing nature of the Internet was a huge boon to content creators, and some unlikely success stories marked the webcomics scene of the early 2000s. Bob and George was the first of what would come to be called “sprite comics,” using the 8-bit pixelated graphics of the Capcom Mega Man games as actors in parodies of the series. Creator David Anez originally planned to draw it by hand, but without access to a scanner he resorted to cutting and pasting sprites into panels. The approach took off, with a massive boom of sprite comics following in its wake.

American Elf

When James Kochalka began serializing his American Elf comics online in 2002, it was a bold new venture for an artist who had previously mostly published through the traditional small press. Kochalka wrote and drew a four-panel diary of his life’s moments, big and small, eschewing traditional punchline structure in favor of creating something more honest and personal. Diary comics had been done before, but Kochalka brought the concept to a new online audience and for several years afterwards Tumblr and Livejournal overflowed with artists delineating their daily lives.

Achewood

Chris Onstad’s Achewood marked a turning point for webcomics. As the browsing audience matured and diversified, they started looking for content that was more in tune with adult sensitivities. In 2003, that was the ironic, iconoclastic world of Achewood, populated by a group of oddball anthropomorphic animals like depressive cat Roast Beef and innocent otter Phillipe. Achewood offered a truly adult webcomic, one that discarded any of the medium’s tropes to deliver a reading experience that was incredibly funny and often disquieting. The strip’s continued popularity, despite being updated only sporadically since 2011, is a testament to how important it was to a generation of readers.

Questionable Content

Jeph Jacques launched his slice-of-life strip in 2003 and by the next year was one of the first artists to make a living solely from his webcomic. Questionable Content follows a group of friends in Northampton, Massachusetts as they fall in and out of love, work lousy jobs and more. Jacques’ keen ear for dialogue and knack for creating relatable characters has kept his audience interested for fifteen straight years of daily updates, resulting in a single continuing narrative of nearly 4,000 installments. That kind of long-term storytelling would become a hallmark of the webcomics form.

A Softer World

It looks like 2003 was a remarkably fertile year, as it also saw the debut of A Softer World by Canadian duo Joey Comeau and Emily Horne. Departing from the usual narrative art traditions, each strip is three panels of doctored photographs with darkly humorous text laid over the top. Oftentimes, the addition of alt text, visible by hovering over the strip, adds an extra dimension to the piece. Although it’s structurally the same shape as a normal newspaper comic (and indeed ran in The Guardian for a bit), A Softer World let webcomics push into new spheres of art and poetry.

Hark, A Vagrant

At first glance, the comics of Kate Beaton’s Hark, a Vagrant seem like dashed-off afterthoughts, drawn in a loose and sketchy MS Paint line with uniform panels stacked vertically. But the inner life of the Canadian artist is wonderfully rich, touching on historical figures, literary fiction and autobiography with grace and wit. Beaton’s work was originally made for her LiveJournal account before being spun off into her own website and a series of successful print publications. Beaton’s art style and subject matter was hugely influential, becoming a frequent source of memes and reaction images.

Dresden Codak

For much of the history of webcomics, artists were limited by bandwidth and compression to crunching their artwork down into limited color palettes and small files. As broadband started to cover the land, that changed, and one of the most important strips that pushed the visual aspect of webcomics forward was Aaron Diaz’s Dresden Codak. As Diaz worked through “Hob,” the first major long-form story arc of the series, his pages grew more complex and lushly rendered, with epic landscapes and a wide variety of panel structures captivating the eye. Plenty of talented artists had worked in webcomics, but Dresden Codak came along at the inflection point where the delivery system could keep up with any kind of detail the creator wanted to include.

XKCD

With no appreciable drawing skills to speak of, Randall Munroe is an unlikely webcomics innovator. But his long-running xkcd came at just the right time, capitalizing on the beginning of the “sharing economy” with chart-like comics that combined data visualization with unusual topics and a sharp but kind-hearted sense of humor. Munroe’s playfulness allowed him to experiment with innovative delivery mechanisms, including a massive panel embedded in a small window that users could click and drag through and a story that updated every hour for four months. Comics like Matthew Inman’s The Oatmeal (wildly successful in its own right) wouldn’t exist without xkcd showing the format — text-heavy explainers with primitive artwork and minimal sequential storytelling could work.

Married To The Sea

The Internet has grown into a fertile engine for mash-ups and content cross-contamination, and Married To The Sea showed that even without an “artist” at the drawing board a strip can be compelling and hilarious. Created by the husband and wife team of Drew Fairweather and Natalie Dee, each installment is a repurposed Victorian clip art illustration with text attached that veers from the bitterly sardonic to the gently absurd. Drew and Natalie don’t take credit for individual strips, making it a truly singular collaboration that comes into its own voice. The idea of collage as a basis for comics would find flower in many other strips to come.

Octopus Pie

Meredith Gran’s Octopus Pie took the slice of life genre that had been growing in popularity and gave it a modern makeover with clear story arcs and a sense of narrative development. Following a duo of Brooklyn roommates, Hannah and Eve, the strip folded in deep doses of social satire with a remarkable amount of humanity and growth. It was also notable for incorporating magical realism into the everyday events depicted — although not a “fantasy” comic per se, Octopus Pie was willing to use detours into visual allegory to expand the emotional space its characters lived in. From the business side, Gran was one of the first web cartoonists to use crowdfunding platform Patreon as a way to expand her income from the strip, using the funds to hire a colorist that gave the project a new, more professional scheme.

Homestuck

Andrew Hussie had been drawing MSPaint Adventures for two years before he began that site’s fourth serial, Homestuck. On the surface the story is about a quartet of teenagers who get their world turned upside down by playing the beta of a new online game, but it quickly ballooned to a cosmological epic of labyrinthine proportions, comprising over 8,000 pages of rich, complex storytelling rife with inside jokes, references and worldbuilding. Unlike many of the other comics on this list, it’s hard to see a wave of Homestuck imitators coming in its wake. Hussie’s singular vision isn’t something that’s particularly easy to duplicate. But Homestuck, which ended in 2017, shows a path forward for a webcomic as a self-contained ecosystem capable of supporting a massive fandom all on its own.

Hyperbole and a Half

Also launched in 2009, Allie Brosch’s brutally honest Hyperbole and a Half took some of the most notable limitations of the webcomics medium and spun them into success. Hosted on Google’s free Blogspot platform and drawn with Apple’s Paintbrush tool, the strip delineated Brosch’s life in rural Idaho in unsparing comedic detail. Departing from the tradition of diary strips, Brosch used long-form narrative to delve into her struggles with depression and other deep issues. The strip went on hiatus after a print collection was released, but her warts and all approach can be seen all over comics on Twitter.