5. Lindsay Lohan’s Courtroom Contour Catastrophe
Court appearances can be stressful enough without the added drama of bad makeup, but sadly, Lindsay overlooked this. In 2011, she showed up to court with a contour so off, it looked like she’d been playing with finger paints in the backseat of the car.
The shade was way too gray for her skin tone, and it was applied in this weird stripe that sat awkwardly low on her cheeks—like, not even pretending to follow the natural bone structure. Instead of lifting her face, it kind of dragged everything down. Not ideal when you’re already under a microscope.
6. Drew Barrymore’s Press Tour Powder Puff
During the press run for Charlie’s Angels: Full Throttle in 2003, Drew Barrymore had one particularly rough red carpet moment. Her setting powder was so reflective under the flash, it looked like she’d dunked her face into powdered sugar—especially around her eyes, temples, and even in her hairline.
Then there was the yellow eyeshadow she wore to a press event in Australia. It covered her whole eyelid, all the way into the inner corners, and was paired with a bright red lip. On their own, maybe those elements could’ve worked. Together? It felt more chaotic than cohesive.
