Not the funniest thing I've seen, but maybe the funnest.

It was late summer, 2006 and I was on the White Rock Creek MUP, here in Dallas. As I came around a bend, I saw a bunch of young ladies running in the grass, along side the path. I got closer and saw that several of them had "SMU" across the back of their shorts.
Since safety is, of course, my primary concern, I slowed waaayyy down as I went past them... Once I got by and around the next curve, wouldn't you know it? I had to stop and check my rear tire . I stayed focused on my bike so I didn't look like some perve, stalking them, (even though, I guess that's what I was doing).
After they came by, I had to pass them again. I smiled the rest of the way to work.

At work, I did a quick google and found out this was the SMU Women's Cross Country Team.
Probably one of my best commutes, ever.