My 2 favorites:
1.
At a convention in Montreal somewhere around 2002, a friend and I sat at the bar and came up with an affiliate program idea to be developed on crackpays.com. The idea was to create an entire line of paysites around crack whores and the like... including reality show type sites. The professional feedback from one well-known affiliate program owner? "It's not worth creating a program around just one genre."
I believe it was sometime in 2003 that Dirty D came out with his stuff and I don't know when that black vagina guy came out... but needless to say I felt like someone had been listening in on our conversation that day in the bar and taking notes.
2.
I never really made plans for this domain, but it's my favorite domain purchase ever: asianbangcock.com