Epic Portrait Fails

What's below are 30 of the most Homeric, epic-class portrait fails in the history of photography. With the exception of the last three, all pictures courtesy of Sexy People. All captions are courtesy of a certain misanthropic blogger with way too much time on his hands.


Extreeeeeme incipient spinsterhood!!!!!


And yet, Tim Burton still thought Wil Wheaton was too gay to cast even as Robin. Life is cruel, sometimes.


And still they thought the Goth lesbian look would become a permanent part of the American counterculture.


So fuckin' bitchin', man, he's got PMS.


"No, seriously, Joana, that hairstyle perfectly conceals your vestigial twin. Really!"


Even if they are obviously celibate for the week, friends don't let friends get expensive portraits done during Spring Break.


Mark fancied himself to be the coolest Carl Ballantine impersonator on the block.


Meet Jesse. Happy Jesse. Shiny Jesse.


Yet, coincidentally enough, both the kids look like Stanley's wife's Swedish masseur.


Cholic or a horrifying prescience of the internet? You be the judge.


Ah, the 80's: Prince. Hair Bands. Pensive gay Hispanic rednecks.


The tense standoff between Meghan and the Goodie Barrette Company reaches its nerve-racking 181st day.


Stoners and the Prom Queens Who Love Them: Next on Jerry Springer!


Morphing into psychotic Billy Bob Thornton in 3... 2... 1...


Palinitis, n- An overmastering desire to use shiny, reflective surfaces to turn oneself into a human palindrome.


Justin's 20/20 vision and non-special needs look always made him feel like the Marilyn Munster of the Farkle family.


Earl and Bubba always looked forward to Portrait Day, the one time of the year when their parents would let them out of the attic. But during the rough patches, plaid always united them.


Boy, I remember the first time I stepped into virtual reality during an Olin Mills Portrait.


If you feel the need to color-coordinate your shirt, jacket and tie with your facial hair... you're a redneck.


So, if one kid wins the National Spelling Bee, are all you kids going to win the National Spelling Bee, too?


.oO They have to feed me, clothe me, pay money to photograph me and open the door for me 20 times a day. So who's the planet's superior life form again? Oo.


Yet, amazingly, even after college, Harry remained unmarried. And celibate. And unkissed.


"I can out-nerd anyone in this whole mall!"


That's right, ladies. You can unwrap Chad all day long on Christmas morning. Just be careful when you pull off the stick-on bow (not seen).


Poor Wayne and Jeffery had the misfortune of getting the only child photographer in North America who focused his young clients with a headless rabbit.


I don't know what's creeping out poor Mr. Toonces more: Getting his skeletal structure crushed or the wildly, ineffably redundant mullet.


This was the guy who had Quarterdeck watch the night the USS Cole was bombed. Think it's about time he got a new AA sponsor?


Who needs putas, right, homies?


No, this wasn't taken at a wedding. This is how everyone looked every day in 1988.


"Say, 'Magic Mushroom!'"