I'm going to question this immediately after posting, but fuck it:
(in chronological order)
1. Bob Dylan, Visions of Johanna (1966)
Believe it or not, this wasn't a lock. I went back and forth between Dylan and Joni, wondering not which made my tastes look more unique, but who could also stand-in for other contenders. By including Dylan's distinct poetic and impressionistic words and atypical vocal delivery, I do manage to pick up some Joni's merits (along with other vaulted singer-songwriters) and Dylan also represents an appreciation for at least some sector of classic rock. It's not a totally deep cut, but also not a "single" or one that is well known outside people who at least are familiar with Dylan's work; identifying myself as a "beyond the hits" Dylan fan will for some people reveal a certain level of music nerd status, even if they don't know how steeped I am in "Dylanology". Last, by including Dylan, it seemed slightly unnecessary to also list a couple of my other favorite artists, Pavement and Steely Dan, mainly for the intelligence, humor, and defiant snarl of the lyrics and their delivery. With so many songs to choose from, this took some time and might not be the best option, but I wanted something prettier and longer, while still containing a good melody and personality/not overly serious.
2. New Order, Temptation (1987 version)
Listing this right after Dylan is a pretty big 180, which tells whoever is listening to the tracks I have some variety. It was important for me to choose a song that had a big electronic presence, but still contained guitar elements, in order to fully cover the New Wave of the 80s. New Order represents not only my appreciation for Depeche Mode and The Cure and others of this era, but also the rest of the electronic music I was into the rest of the 80s and early 90s, and one could extrapolate "hey this guy might also be into LCD Soundsystem, Cut Copy, Wild Nothing, Chromatics, etc."
3. Prince, Alphabet St. (1988 album version)
Took me a while to land on this, maybe if I took even longer I'd find something even better. While it probably wouldn't make my Prince Top 10 (tho it would be close), it seems to have a little of everything Prince came to be known for: a distinct groove (though not overly so to falsely advertise myself as a huge funk fan) with a modest but memorable guitar part, some horns peppered in, organ and toy piano sounds in the later sections, female backing vocals including a brief rap, male call-and-response b.vox, sampling, some guitar shredding that's a little low in the mix but enough to dirty it up, and also a catchy melody that illustrates his gifts as a pop songwriter. It's a sonic smorgasbord that manages to avoid sounding overstuffed or directionless. While I hate to try and fit all genres of music dominated by African Americans under the banner of one artist, at heart I'm still a rock and roll fan above all and it's more important to me to show how much variety within that sphere I enjoy more than trying to prove that I'm down with hip hop, soul, funk, or jazz (this song should be at least a step into most of those). I had originally hoped to partially tick off the latter box by listing Steely Dan but it wasn't worth it.
4. Bettie Serveert, Keepsake (1995)
Many candidates for who would represent my beloved "Matador in the 90s" era, and for a while I just assumed that would be Pavement. I wanted something lo-fi, maybe a little druggy. When I decided to drop Joni, I started thinking Liz Phair could pick up that slack of personal, intelligent lyrics, unique guitar tunings, etc. but it was hard to find the right song, and I wanted to make sure that my list in general had more "jammy" or soloing guitar work. This isn't my top song of the Betties in that regard, but Peter Visser does get to shred, it has the right Matador aesthetic, a combination of slow and driving rhythms, and the female vocals of Carol van Dyk, who may not be Joni or Liz in the lyrics department but still has her own odd perspective.
5. Carly Rae Jepsen, Boy Problems (2015)
A big 20 year jump here, but to I need to tell a stranger that I'm into the "return of rock" from the early 2000s? Or that I love Radiohead? This entry could have been a number of other recent pop acts, but there's nothing special about saying I'm another of Rihanna's legion of fans, nor did I opt for the brainy, intersectional Janelle Monae. In a sense, this is here to say, "I can enjoy 'shallow' pop music too if it's done well", and also means I can cover some territory missed by not including Madonna, whom I love. And it's also important to say that however far back or diverse my tastes go, I'm not totally oblivious to current music. CRJ may not be the perfect choice here but she's representative enough, and like Kabigon, I went with one of her deeper cuts (which is my fav on the album anyway).
