Will Colbert is one of my favorite cameos on the show as he was played by Brad Pitt who was married to Jennifer Aniston at the time.

He plays a school friend of Ross and Monica all grown up. He was apparently obese like Monica was and (just like his friend) had made a remarkable glow up in his 30s.

When he reunites with Ross, he brings up Rachel Green whom they both organized a hate group for. Will hated Rachel for bullying him back in school and Ross “hated” her for not dating him back in the day. Ross really is the worst person.

And of course, Rachel is kind of oblivious about the whole past with Will. Which would definitely infuriate somebody who had been in Will’s position.

But he kind of gets his revenge when Rachel’s told that Will and Ross had come up with the rumor that Rachel had been born hermaphrodite and that rumor stuck pretty big that even Chandler knew about it and he didn’t even go to the same school.