Alright, so last time around I claimed I was ready for advanced baby name discussion. So here's an attempt:
I've been thinking recently about the concept of a "cool" name. People have all kinds of motivations for picking a particular name for their baby, but coolness is definitely one of them. But then, coolness is also generally considered to be generational...parents are inherently uncool. So how can a name picked by parents to be cool be cool?
One theory is something that I think we already kind of know....coolness really isn't that generational. Kids who are cool usually have parents who were cool (and kids who aren't cool usually have parents who weren't cool) so the cool names of any generation are going to be whatever names the cool people of the previous generation like. They teach their kids what to like, and so its a self fulfilling prophesy.
Another theory is related, but not necessarily exactly the same...there is no such thing as a cool name. Cool kids make their names cool. You can give your kid the exact same name as the most badass badass in school, and on that kid it will seem cool and on your kid it won't.
And then the last theory is that the actual cool names are normal names. Trying for coolness is doomed.
In practice, thinking this all through requires remembering what names I thought were cool when I was in elementary - high school. I'm pretty sure in elementary school, the coolest name that anyone I actually knew had was Melissa. I have no idea why I liked it. I was a dork and wanted to turn it into a name that was more unique and special, so I discovered Millicent, and that was my "favorite" name for a while...but really I liked Melissa. And then by high school, I'm pretty sure it was Joanna (plus some of the completely un-Americanized names my classmates had, but I think those have to go in a different category because liking them didn't make them part of the menu of options I had for naming my own kids, at least by my interpretation of what the "rules" are). So I guess that's overall a vote for normal-for-their-generation names. Melissa I think also hints at a preference for newer names...none of my classmates' moms were named Melissa. Joanna (the 88th most popular name in my birth year vs. number 8 for Melissa) I think shows a growing appreciation for timelessness and not being too popular. Both are three syllable, melodic names...of exactly the type I didn't have or give my daughters. Neither one is cool specifically because of the person/people I knew who had it.
I'm not going to list the uncool names, because that's just mean...but they definitely tended to be attached to just one person, and just one person I didn't think was especially cool. I can think of plenty of instances of a unusual name seeming normal because the person with it was so normal or was someone I was close to, but none where I thought someone was a complete dork but had an awesome name. I can actually kind of remember some cognitive dissonance in this area. There were names I wanted to like because they were unique or old fashioned, but I just kind of didn't. (And again, not talking about anyone I was ever close to here...this only seems to work for people who the main thing you know about them is their name).
But obviously, I wasn't really the arbitrar of cool growing up, so my sample size of one is pretty useless.
Oh, and ironically...the coolest name I ever liked as a kid by my current standards would have been the one I picked when I was about three and decided to name all my dolls Alice after my great-aunt.