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Digital Art History from a Silly Daddy, Star Chosen, and Old Pocket PC Perspective

Joe Chiappetta draws Silly Daddy Comics on Pocket PC

Looking Back at the Past 25 years to Look Forward

Joe Chiappetta, 10/30/2025

Since the earliest days of Microsoft's Pocket PC in 2000 AD and later, the Pocket PC Phone, various art and drawing programs were available to load onto the Windows Mobile platform. While this operating system eventually lost out to the more famous ones of today (Android, Apple), with the right software back then, such devices--because they came with a great and resonsive stylus--were transformed into virtual, but miniature, art studios. Mind you these were really fully functional mini-drawing tablets decades before Apple Pencil and e-ink drawing tablets were available.

Yet are there any visual artists who consistently created viable bodies of artwork on such pocketable gadgets who are still active in digital art today? From the digitized word balloons of myself, a longtime cartoonist and digital artist, the answer is a resounding "Tap Stylus Here!"

Silly Daddy Forever comic book ordering page

While my long-running series, "Silly Daddy," contains comics drawn on all types of media, what's noteworthy to the digital art and mobile device community is that over 500 of those cartoons were created entirely on devices running Windows Mobile (as of 2009). After that milestone, I stopped counting. This creative utilization includes phones and personal digital assistant devices (PDAs). The last device of choice I used for Windows Pocket PC was the HP iPAQ 210 Enterprise Handheld, with its 4" screen. I drew, lettered and colored webcomics on that Pocket PC using Conduits Pocket Artist software (a mini version similar to Adobe Photoshop) or Vectorsoft Draw (a mini version similar to Adobe Illustrator).

Other Windows Mobile devices that I, for my "Silly Daddy" comics had used to create webcomics include the Samsung Omnia phone, the Verizon XV6700 (HTC) phone, the Verizon 6900 (HTC Touch), and from back in 2002, the die-hard Compaq iPAQ 3955.

The comics created entirely on mobile phones even spawned their own art subcategory: "telephomics." I do warn however, that when artists aren't using an earpiece while making telephomics, they can expect the drawing process to be interrupted frequently if a lot of phone calls are coming in. Such is the lot with all-in-one devices.

Back in the day, I also used the word processing power of Microsoft's Word Mobile program, which came standard with the operating system, to write out story ideas and Silly Daddy dialog. I even used the Pocket PC in 2005 to start writing a large portion of a full length science fiction novel (finished 20 years later), but that's another story altogether... called "Star Chosen."

Star Chosen science fiction novel - book ordering page

What all this digital art retrospective has done for me is quite profound. I see how far technology has advanced in the past quarter century, yet also how much all is still the same. Indeed, the handheld devices of today now do literally everything. But as for me, at heart, professionally, I am still somewhat like the patriarch Jacob. I have blessings which I am most grateful for, yet I believe I will receive even more. So I keep wrestling all night--not just with God as in the case of Jacob--but also with the ever-evolving digital art and publishing ecosystem. I won't let go until the blessings of being a digital creator are fully realized... or until the power goes out.



I invite you to read more about my digital art journey in a recent interview conducted by Digital Arts Blog. I'm so grateful to Cansu Waldron there for interviewing me about my long history in the arts! It was an absolute joy, privilege, and a blast to be featured there, as Digital Arts Blog has an impressive track record of crafting top-notch coverage of the digital art field! Cansu's insightful questions pulled so many unexpected and deep truths out of me--even career-enduring patterns I had never fully formulated until recently! We go into behind-the-scenes art-centric topics in a fun and fascinating way that I hope all can appreciate! You can read the interview at https://www.digitalartsblog.com/artist-spotlights/artist-interview-joe-chiappetta.