Embarrassing Photos – Zimlinghaus, Fink, and Hailes’ Headshots


comediansdouchechillz originalsembarrassing photos

We asked some comedian friends to send us their reject headshots — the ones that didn’t make the cut due to high douchechillian factor of their poses, facial expressions, or general appearance. Here are the first three.

roger hailes headshot


“Hey, we all like boobs but there is a time and place for everything and your headshot is not the place nor the time.” – Roger Hailes

Roger Hailes is an NYC-based comedian.

kenny z - cosmo radio - douchechillz headshot

“I get douchechillz from this headshot cuz it does nothing to show that I’m a comedian. This headshot looks like I’m confused by stocks. Like “oh hey, I’m that guy who lets you get away with nothin’! Yeah. Kenny Z!”

-Kenny Zimlinghaus, comedian.

heather fink - embarrassing photos for douchechillz

“So check this shit out – it’s horrible – and don’t worry, when I made this jpg I made sure to watermark it with my url. I also used my FULL NAME to help me be a hollywood actress. These photos were taken when I was 16, and placed on the website I made in 1999 following my “Internet and You” class in high school.”

- HEATHER FINK, comedian and filmmaker.

More on the way!


Send us your photos — professional portraits, headshots, or regular old embarrassing photos of yourself that give you major douchechillz? Tell us why.

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