Known universally as the most abominable of all hats, no self-respecting celebrity would be caught in a fedora today. But back in the 2000s, the horrendous piece of headwear was a favorite of all your favorite (and least favorite) stars. It feels like Justin Timberlake had one for every day of the week.

So in case you were having any nostalgic warm fuzzies about the era, here are a handful of unfortunate fedora moments from the turn-of-the-millenium to set you straight.