Young Brad Pitt
I'm sure Brad Pitt wishes this photoshoot never happened. Even stars probably cringe at their adolescent selves being horribly awkward. Brad Pitt at least still went on to have an insanely successful career.
No Scurvy For Leo
Okay, if Brad Pitt was cringe, you might want to look away. Leonardo DiCaprio subjected himself to this insane photoshoot, impersonating Carmen Miranda. However, the worst part of the shoot is definitely those jeans.