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Smile! Say cheese for your new AI headshot

Smile! Say cheese for your new AI headshot

My headshots are woefully out-of-date. They’re from just before the pandemic — the last time I really went into an office. Luckily for me, technology has advanced to help me get up to date: Enter the AI-generated headshot.

A bevy of new artificial intelligence tools now promise to generate professional-quality headshots — for a new job, a dating profile, etc. All you need is to upload clear photos of yourself, and the software spits out a series of realistic images for you.

Inspired by The Washington Post, I decided to try two services: and Try It On. The functionality of the two websites was nearly identical: I uploaded some photos of myself that I thought were nice and paid a small fee of $35 for Aragon, $21 for Try It On, and waited about a half hour for each website to do its magic. When my photos were ready, I clicked and instantly laughed. It gave me full glam.

Both services gave me a lot of photos. I downloaded 100 from each, including a fake version of myself, ones with me in different outfits (suits, cardigans, t-shirts), and different backgrounds (office buildings, nature scenes, streetscapes). Some were moody noir shots, others casual pics primed for a dating app, and some very traditional and corporate — for a LinkedIn profile.

The quality was variable: Some were very good, some were not. My wife and I flipped through, with her commenting “That looks like you!” and “Oh my god that's terrible” and even “Oh, he's cute. I like him.” The software generally had a slimming effect on me, and gave me a squarer jawline and pronounced cheekbones. I was most impressed that it seemed to understand the contours of my hair.

Most of my headshots were still noticeably artificial and not quite at the level where we should worry about deception. Some of the “good” ones either look heavily Photoshopped or like I got a lot of plastic surgery. There’s a term in art and science fiction called the “uncanny valley,” a phenomenon that occurs when someone sees a face that's not quite human — a uniquely eerie sensation, like recognizing alien life. For now, my AI-generated headshots feel like they belong in the uncanny valley.

While there were a few headshots I could use, the technology has a ways to go to avoid alarming folks into thinking I’m a cyborg.


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