(I'm guessing that the top pic is a gay vacation boat. Otherwise, it would seem that symbolically the figurehead is a female being "ridden" by the ship).
When I was a kid, we had a cabin cruiser at our summer home. It hardly ever ran. Seemed like my father and brother were constantly trying to remove barnacles and pump the bilge, having trouble getting it started. On the occasions it ran, we tooled around Mobjack Bay on the Chesapeake and visited the abandoned lighthouse on the rock island.
I used to complain to my father our boat needed a figurehead. I tied my Barbie to the front of it one whole summer and no one ever even saw her there. I did. I watched the wind blow her hair and thought--I want to be her!
It's been an obsession ever since. Some day, I would really like to acquire a weather worn one and have it jutting out of the wall over my fireplace. I also would love to get a nice shot of myself as a figurehead some time. It's ambitious, but I think it'd be really fun to pose, hair whipping around me and immortalize myself as one of my favorite inanimate objects. Hell, when I modeled I already posed as a mannequin in a store window, so all I need to do is dress up as a ventriloquist doll and a clown and I'll have covered some of my creepy obsessions.
What started the figurehead craze? It began in the 16th century on the galleons. Viking ships had some nasty ones that warded off evil, but the ornate ones we recognize nowadays come from the baroque period when the ornaments got so large that they could weigh tons! They were used to show name/status of the ship. This affected the sailing abilities of the ships and were costly, so during the 18th century they began to make smaller half-figures. The clipper ships of the 1850s and 1860s customarily had full figureheads, but these were relatively small and light.
It doesn't take much stretch of the imagination to figure out how the term "figurehead" came to be when describing someone with a position of prominence but no actual useful purpose. Yeah, sort of like Dale the Doll is the figurehead of GHT!