I think the highlight of my DJ career was after thoroughly rocking the back room of the student disco, using an array of drum 'n' bass records that I had just purchased for way too much money the previous day, a girl told me that it was quite good, and I got paid a fiver (there were four of us DJ-ing and we divvied it up).
The low point was probably being asked to DJ at a mate's wedding earlier in the year. I know there are a different set of rules in effect on such occasions, but I still decided to see whether I could get away with playing a tasteful set of funk, hip hop and soul with a few recognisable cover versions thrown in (e.g. Mary Wells's awesome version of "Satisfaction") By the third song only two people were dancing – my girlfriend and a bloke wearing lederhosen.