1. How the show started:
2. When he was asked if he'd ever date someone older than him.
3. When Hugh caught Andy completely off-guard by asking him about an old hook-up.
4. When he tried to defend the fascination with Pippa Middleton's butt but then failed spectacularly.
...Or maybe never?
5. When a caller asked if he's "still close" with Julia Roberts.
6. And when Andy called him out for his remarks about it "being difficult to kiss her because the size of her mouth."
7. When he insulted Andy Cohen during a Notting Hill reenactment.
8. On why he and Elizabeth Hurley's relationship didn't work:
9. To Sarah Jessica Parker after Andy Cohen brought up how she used to clip his toenails on set:
10. And then when this happened.
