I thought this was a question that should get some funny answers! I'm looking for the whackiest job you've ever had, or the weirdest client you've dealt with. Maybe the oddest request?
For me, I used to help people create CVs and resumes, and I had one guy who was the chairman of his local VLARPing group. VLARP stands for Vampire Live Action Role Playing. I understand being the chairman of an organisation is a positive to put on your CV, but I had lengthy discussions over the fact that it could put future employers off because of the type of hobby (I've worked in recruitment, I know how quickly people can go off a resume or a CV).
The best part was, one of the women I used to work with in recruitment contacted me because she was an interviewing for a job and got him as a candidate. She told me that during the interview when he said 'role playing' she immediately assumed he meant that they did interview techniques and roleplayed as part of that (it was her only experience of roleplaying before then) and then he went into a lengthy 15 minute discussion about the Vampire Society they had, and what it was all set up as. She couldn't stop laughing while she was on the phone. He gave her their website, and we went on and the website was VERY sexually oriented...
I still wonder if he ever got a job, and where.