I think there are 3 types of people in the world: those without nicknames, those with nicknames, and those with pretty good nicknames.
Barack Obama is definitely not a nickname kind of guy. Folks have tried silly things like “Barry” or “Bam-Bam” but they never stuck.
On the other, Bill Clinton was ripe for nicknames, and I thought “Bubba” fit pretty well.
Athletes and entertainers should be right in the nickname wheelhouse, but most come off as lazy (A-Rod, J-Lo) or more marketing hype than anything else (99% of the names on this list: http://www.pr.com/article/1020)
Personally, I’ve had a run of nicknames and all seemed to fit the moment. When I was very young, I somehow got tagged with “Snuffy.” http://en.wikipedia.org/wiki/Barney_Google_and_Snuffy_Smith I didn’t like it or hate it. It was just kind of there and lasted well into my teens.
Once I hit college, I picked up a few: Schmitty, of course, and the off-shoot, Smitty. But, mostly I got G-man, which I kind of liked. I’m not sure whether I had that before or after Mike Gminski (we were at Duke together) http://en.wikipedia.org/wiki/Mike_Gminski, but he was definitely the more famous G-man.
After college, I seemed to pick up “G” from my golfing buddies but it didn’t get wide circulation.
About the time I started writing for theStreet.com, though, I adopted Gary B. Smith as my byline (there was a Gary Smith writing for Sports Illustrated when I was writing for them and my SI editor added the “B” to my name. From then until now, “Gary B.” seems to have stuck and even Nancy calls me that at times.
Naturally spousal nicknames fall into a completely different category, most of which are endearing but silly to anyone outside the family. I call Nancy “Bunny” all the time and she calls me “Dad” a lot. I guess that’s something you pick up when you turn about 50. I find it sweet.
In looking back, I’m glad I had nicknames and really glad I never had mean or nasty ones. If “Snuffy” is the worst I’ve been called, I made out pretty good.