Ah, Kylie Jenner, the first of the Kardashian clan to grace this list. When Jenner came out with this wheelchair-BDSM inspired photoshoot for Interview Magazine, the disabled community was rightfully upset.
They have been marginalized from society for years, but Kylie’s attempt to capitalize on that fell flat. Sorry, Kylie, but this photoshoot will haunt you forever.
No One Wanted To See This Spread Eagle
This is one of the photos that you look at and immediately know is wrong, but you can’t stop staring. Maybe it’s Sarah Jessica Parker’s stone cold expression, or maybe it’s the awkward water bottle placement right between her spread legs. Either way, it’s one of those photos we’d be happy if we never saw again.
The next few photos celebrate the cringiest boy band photoshoots from an unforgettable era.
The Coolest NSYNC Has Ever Been
I understand that frosted tips were a trend in the late ’90s, but this is taking it a step too far. Not sure which one is better: Lance Bass’ one frosted eyebrow or Joey Fatone’s fully frosted beard.
There’s a 110% chance that this photo was taken for a teen magazine and this photo hung on the walls of thousands of teen girls bedrooms. But just because it was popular, doesn’t mean it’s right.
Praying For The Comeback Tour To Actually Work
Stay with me, because there’s a lot to unpack with this Backstreet Boys photo. A.J. looks like he’s a mob boss, but Brian is right beside him striking a pose that would be much more appropriate crouched down beside his 1983 used Chevy Impala.
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