It occurred to me recently that my two favorite pop songwriters of the last 25 years – Fiona Apple and Stephin Merritt (The Magnetic Fields) – on the surface seemingly couldn’t be more different. So why should they both be personal favorites of mine? True, both are astonishingly gifted, but there are other talented songwriters out there as well.

Part of it is just happenstance and stylistic affinity. And I have nowhere close to as broad a sense of what’s going on in the music biz, even limiting it to the relatively rock-affiliated space, as that which I had, well, let’s just say some decades ago. Nor am I (admittedly) as open to new things as I was once upon a time, and these are both among the sorts of artists who get (well-deserved) rave reviews on the apparently-soon-to-be-defunct pitchfork.com.

But then it occurred to me that there is actually an odd commonality to them, which consists in part of their responding in almost opposite ways to the same underlying problem.

Both were born in the rock era (Merritt 1965, Apple 1977), and were very influenced by it. But both are also much more broadly and eclectically grounded in popular music, including that from the pre-rock era (e.g., show tunes). But the problem to which I see them alike responding is that of writing great popular music after so many decades in which this territory has been so thoroughly covered. After the Beatles, Dylan, Carole King, Motown, Brian Wilson, Patsy Cline, Lou Reed, Ray Davies, and so much more for so long, I would think that it’s hard to avoid feeling a bit self-conscious, as well as derivative of one thing or another, when one is trying to write songs in this space.

Fiona Apple’s response is to be so raw, unfiltered, and utterly un-self-protective as to blow past the models she surely has. Try writing a memoir in the spirit that she writes her songs (at least, pre-Fetch the Bolt Cutters). It would be verging on impossible to make oneself do it, even if one had felt things as deeply as she evidently has. Now, there’s no lack of very conscious and careful artistic shaping of what she does – for example, beautiful melodies, nice piano riffs, odd and shifting time signatures, what the Beatles liked to call “middle eights,” carefully arranged intros and outros, loud-soft-loud and rough-sweet alterations, extended metaphors, and big vocabulary words. But she lays herself out there in a way that very songwriters or performers can.

I admittedly haven’t really gotten in to Bolt Cutters (rated 10.0 by Pitchfork), although I ought to give it another shot. My thought upon hearing it was that she’s happier and more contented now, which is great for her but not as good for the work. (That change is also commonly a part of growing older, and hence related to why so many great songwriters of the last six decades have failed to sustain their levels past their early thirties.)

She also may have grown tired of writing from so far out on the edge. She has commented in interviews about how tough it is to perform songs that she wrote when she was upset about something, because it forces her to relive her worst moments while on stage. That concern might inspire the self-censoring self-protectiveness that her three previous albums avoided.

Stephin Merritt’s response is to be completely self-protective. Nearly everything is layered deep in irony. 69 Love Songs, for example, is not “about” love – it’s about love songs, indeed as promised by the title’s double entendre. And not just love songs, but, through them, all the artificial or cliched or simplistic or overly self-conscious ways of thinking about love, instead of just experiencing it, to which we all fall victim given the huge cultural weight of all the “content” that we have absorbed about it.

True, he tried to fight against this in 50 Song Memoir, although part of what’s going on there is that he likes to set difficult songwriting tasks for himself (e.g., one of his albums is limited to songs that begin with the latter i, and that appear in alphabetical order). But, although I thought parts of 50 Song Memoir were great, it’s more uneven than 69 Love Songs, perhaps reflecting that this was a harder space for him to work in.