My list for the Tillerman, the greatest dinghies of all time (that I have sailed):

1. 505.  The greatest doublehanded racing dinghy of all time, indisputably, as well as the prettiest.  Not to mention one of the toughest classes.  I raced in the 505 Worlds in, um, 1990 (had to think about that), in Kingston Ontario, finished about 50th in a fleet of 100 boats, and rate that one of my best regattas ever (that was back when I could sail).
   
   
2. Laser.  The greatest singlehanded racing dinghy of all time, although the Finn would have a case, too.  Certainly the most popular; there are Lasers everywhere.  I've never had any success racing Lasers, exception in local fleets, the class is just too tough.  I've owned three lasers including Locomotive Breath, my current one, which is eight years old; I'm guessing I've had one for over half my life, and hope to keep that going...
   
   
3. C-15.  This is my sentimental favorite, as I've owned my current C-15 It's the Water for 30 years, and have won three national championships in it.  Of course the C-15 isn't as fast as a lot of other doublehanded boats, but it is built better and they last.  (And in enough wind, they do manage to get out of their own way :)  Probably the high point of my sailing career was winning the C-15 International Championship in Japan, in 1978.  Yeah, I was 19; I peaked early...
   
   
4. Snipe.  As the Laser is the most popular singlehander, the Snipe would have to be the most popular doublehander; you can find them all over the world.  They are not fast, but they're fun to sail and durable, and they have a feature which has ensured their popularity: they can be sailed by a guy with his girlfriend.  I owned a Snipe for about ten years, finally donated it to the Alamitos Bay Yacht Club when garage space became more important to me than sailing :)
   
   
5. Hobie 16.  The most popular catamaran of all time, by far; you can find them all over the world on every beach.  They're simple and fun and fast, and at one time there was a huge racing fleet which was amazingly competitive (seems to have died out a bit in recent years).  I raced them off Malibu, and enjoyed their speed and ease of sailing as much as the competition.  They are as happy sitting on a beach as they are in the water.
   

Assembling this list gave me a strong sense of nostalgia.  Nothing is as worthwhile as spending time sailing; my father used to say God did not count time on the water against your allotted days on the Earth.  I need to spent more time "out there"... maybe next weekend, with my daughter (the Westlake Cup Regatta, which I first won in a Cyclone at age 17), or a bit later, the High Sierra Regatta, fixture of the C-15 Class calendar, my first "out of town" race when I was a young teen, wide-eyed with wonder at seeing so many boats from so many places, and Huntington Lake is still one of the best places to sail anywhere.  Stay tuned!