Whitney Houston

Source: LL Cool J, Clive Davis, Randy Jackson, all in memorials
Major generational observations: "I believe the children are our future / Teach them well and let them lead the way"
Legit?: I always hated that line. "I believe the children are our future" — no shit! I also believe the future is tomorrow and the past... was yesterdaaaaaay. These are not radical beliefs. And yes, I know she didn't write the song. But she sang it! Counterpoint: she did have a nice voice.
 

Bob Dylan

Source: Bono, everyone else
Major generational observations: "Come mothers and fathers throughout the land / And don't criticize what you can't understand / Your sons and your daughters are beyond your command / Your old road is rapidly aging"
Legit?: Definitely, even if he never wanted the title. Few people have captured an era better.
 

Kurt Vonnegut

Source: A lot of people, plus Cornell Alumni Magazine
Major generational observations: "Dear future generations: please accept our apologies. We were rolling drunk on petroleum."
Legit?: Yes, I think so. His world-weariness, puckish sense of humor, and contempt for dehumanizing institutions all make him a good contender for voice of the '60s. Dylan probably gets the edge though, because he vocalized revolutionary fervor while Vonnegut was just too damn sad to really embrace that side of the era, generally distrusting fervor of all stripes. (Cf. that scene in Mother Night where the narrator finds himself standing in the street for hours because he can't think of a single reason to move.) On the other hand, given the way things have gone since the '60s, maybe Vonnegut was right.
 

Conan O'Brien

Source: Turner Entertainment head Steve Koonin
Major generational observations: "David Letterman wanted to be Johnny Carson, and was not, and as a result my generation of comedians wanted to be David Letterman. And none of us are. My peers and I have all missed that mark in a thousand different ways. But the point is this: it is our failure to become our perceived ideal that ultimately defines us and makes us unique."
Legit?: Maybe not in general, but certainly in terms of comedy; Conan anticipated the pop-culture-fuelled surrealism that's dominated the past decade of humor, and made older comedians look hacky and out-of-touch in the process.
 

Beck

Source: Allen Ginsberg, of all people
Major generational observations: "I think my whole generation's mission is to kill the cliche."
Legit?: That's a sharp quote, I've got to say. And maybe the mission of the subsequent generation is to find something to replace all the cliches that Beck and his peers killed off with their reflexive irony. This is proving to be almost impossible, incidentally.
 

F. Scott Fitzgerald

Source: Edward Weeks, in a 1942 issue of the Atlantic Monthly; many others
Major generational observations: "I'm a product of a versatile mind in a restless generation — with every reason to throw my mind and pen in with the radicals. Even if, deep in my heart, I thought we were all blind atoms in a world as limited as a stroke of a pendulum, I and my sort would struggle against tradition; try, at least, to displace old cants with new ones." (and a ton of other killer lines)
Legit?: Oh, hell yes.
 

Lena Dunham

Source: Herself, facetiously
Major generational observations: "The idea that I could speak for everyone is so absurd. But what is nice is if I could speak for me and it's resonant for people, then that's about as much as I could hope for."
Legit?: Probably too early to say, but the thoughtful, bright, self-effacing Dunham has as good a shot as anyone. Girls can only be its own story, but by dialing in so precisely on those specifics, it does manage to capture a lot about internet-age kids. Most of the things people say are insufferable about it are clearly meant to be funny, and not in a gross Andrew Dice Clay "hey feminists, where's your sense of humor?" kind of way — Dunham is usually going for laughs at her own expense. Whether she'll maintain VOAG status is up in the air, but I wouldn't mind.
 

Kanye West

Source: Himself, not facetiously
Major generational observations: Rarely talks about anyone or anything other than himself
Legit?: ...which, of course, makes him a perfect spokesman for the most narcissistic generation of all time. OF ALL TIME.

Want to meet the voice of a generation? They're probably waiting for you... on Nerve.