Progress toward perfection has genuine skeptics, who insist on sticking with marginalized tools. The newer thing may seem less flawed or simply easier, such traditionalists insist, but it sacrifices warmth, soul, depth, personality, chance and the human touch. They must have a point, because practically every antiquated creative process ends up inspiring some kind of digital filter, effect or add-on designed explicitly to mimic its singular properties. The upshot is a form of progress toward perfecting flaws.

A conspicuous example is the $1.99 Hipstamatic iPhone application, which, as one review put it, filters images made with the device’s camera “to make them look as though they were taken with an unreliable plastic camera . . . rather than this complex mobile smart phone.” In mid-July it was the 17th-most-popular paid app in the iTunes store; drop by the Hipstamatic Flickr pool to browse more than 53,000 digital images, with pleasingly washed-out colors or other beguiling imperfections resembling those created by glitches in analog processes.

The same urge surfaces in other media. IZotope Vinyl recording software lets users “create authentic ‘vinyl’ simulation,” right down to filters to suggest the amount of dust on a record and the degree of warping. Digital typefaces ape handwriting, including idiosyncratic jots or messy scrawls in dashed-off marker or childlike crayon; others strive to capture the quirks of the hand-painted signage at a small business. Even crudely amateur Web design can now be recreated in a click with the Geocities-izer, which instantly reworks any slick contemporary site into a jarring mess of loud colors and pointless animation reminiscent of an earlier and more individualized version of the Internet — as if it were “made by a 13-year-old in 1996.”

Admittedly, the Geocities-izer is more of a joke than a tool, but it crystallizes the idea of new, easy-to-use methods for recapturing the error-riddled expression of yore. This echoes the long-established yen for “antiqued” furniture or “distressed” jeans: imperfection implies character, imposed by artificial means. Images from the Hipstamatic have “an instant haze of memory,” according to one endorsement. And really, who wants to wait around for the actual haze of memory to set in?

It’s telling that the urge for these tools seems strongest in the realms where bits have replaced film, a medium notable for its ability to capture reality accurately. Aside from the Hipstamatic, various apps allow you to layer a “warm vintage” appearance or “film emulsion” border onto phone pictures or even recreate the look of that classic botch, the double exposure. Users of actual cameras (actual digital cameras, I mean) can also unperfect their images with products from Holgamods and Lomography that re­create the glitchy effects of cheap cameras; Lensbaby mounts do the same and include an option for making pictures that resemble those from a pinhole camera — all to “bring a more organic look.” Silver Efex Pro software aims to make color photographs into convincing black-and-white ones; Poladroid software promises to let you easily create “high-resolution Polaroid-like pictures from your digital photos.”

As for moving film, you don’t have to buy a Digital Harinezumi to fake an 8-millimeter movie: the Vintage Video Maker app converts iPhone videos to resemble a 1960s home movie or even a 1920s silent movie. The unifying theme is the link between the flawed and the interesting. A boringly perfect digital picture of a flower makes no impression. But an equally boring one marred by (digitally recreated) light leaks, exposure mistakes and focus inconsistencies presses the aesthetic button that suggests deeper meaning. Specifically, the image looks like one from a time before taking a thousand pictures in a weekend was routine. It taps into a language that predates digital abundance in order to layer on implied significance where, as often as not, none exists.

Not that anyone is complaining about digital abundance. The number of people who actually cling to what one flaw-tool endorser calls “the oh-so-last-century idea of film” remains small. Another enthusiast concedes the technologies of imperfection fall short of matching the qualities the actual outdated tools produced — but they’re so much easier to use that it’s worth the trade-off. And that raises and answers the question of how to choose among the many options for digitally antiquing your 21st-century self-expression: we want the ones that make the most convincing mistakes.  

This essay was originally published in The New York Times Magazine, November 30, 2003.