We could ask the artists directly, of course. In interviews, Johns Flansburgh and Linnell have always expressed disinterest in the sexist machismo that runs through a lot of rock culture. (This may be why They've attracted a pretty gender-diverse following over the years; They/Them pronouns featuring prominently in the band's branding can't have hurt, either.) Or we could look through the Gender Issues theme on TMBW and draw some conclusions there.
But I believe that even more interesting than an artist's intentional statements are their work's unintentional ones. This page is for musing on some patterns I've observed between songs, considering how they might fit together and reveal underlying philosophies.
Songs written by John Linnell are usually quite gender-neutral. Gender is, outside of the rare private romantic context, mostly only useful to note when a new set of pronouns introduces a new character. Female and male characters are balanced in number and importance.
Most flaws, goals, and anxieties are universal. (This is something like the philosophy of equality feminism.)
In these songs, we're often introduced to a series of characters, all representing instances of the same experience or idea. Each new set of pronouns indicates a new character, another example:
Gender is most useful for keeping track of who's speaking in an unnamed pair of people. (Grammatical gender, that is.)
In these songs, male-female pairs usually represent troubled romantic relationships, but any difference in gender roles is barely acknowledged:
The song Women and Men is, on the surface, probably the most immediately identifiable song that John Linnell has ever written "about gender". However, while the narration may believe the world is divided into "momen and men", these categories are only ever mentioned together, as halves of a whole. No statement about love or human behavior is made exclusive to one or the other.
It's most accurate to say that "woman" and "man" refer to sex here: the only remotely "gendered" assumption is that romantic pairings lead to sexual reproduction. Even so, any social or even biological difference in roles in reproduction or child-rearing is unimportant; that happens off in the jungle.
The sex or gender of the singer is irrelevant. Ultimately, this song is really an observation on humankind's history of migration and population growth. Both sexes are equally necessary for this process. This is more of a scientific statement than a social one.
In songs written by John Flansburgh, gender tends to be much more important. A character's gender comes up as a way to describe their behavior, obligations, or plans, and may be a source of anxiety or pride. The experiences of male and female characters aren't symmetrical; these groups are under different societal pressures.
Gender is a role that must be learned and a title that must be earned. (This is particularly true of fragile masculinity.) To these songs' narrators, "being a man" requires putting in active work to live up to social standards:
Gender may change to describe the role someone is playing at the moment. (Instead of being fixed, based on sex.) It's usually female characters in these songs who try on male-ness for fun or empowerment:
Gendered action is planned with help from others in the same category. (The sociological term for this is homosociality.) Characters in these songs find special cameraderie with others who share their gender, or at least their gendered goals, particularly when deciding how to work with or against the 'opposite' gender:
The song How Can I Sing Like A Girl is probably the most immediately identifiable song "about gender" that John Flansburgh has written, and it is very literally about a performance.
The song hangs on the idea that even outside the world of romance and reproduction, an action can be done "like a girl" regardless of the sex of who does it. This is not a symmetrical equation: being seen as girl-like comes with potential stigma, and being seen as a girl comes with objectification. The song's meaning would shift if we didn't see the singer as a man.
The song title seeks advice from the listener. "How?" isn't asking if it's possible to perform against type, but instead anxiously looking for help with getting away with it. The narrator wants to find community with those with shared gender-goals, to never be alone: a social solution to a social problem.
These songs are an odd pair for comparison—one off a 2000s kids' educational album, the other off a 90s solo album. But both are structured around listing pairs of things, and the way this is handled provides a particularly clear illustration of the "neutral binary category" / "meaningful interactive role" approaches to gender.
from Even NumbersSkip all the numbers that are not even
Leave out the odd ones
Leave out the odd; you're left with the even
Skip all the odd ones
Skip the first number and the second one's even
Skip the third and the next one's even as well
Skip the next, take the next, skip the next
Take, skip, take
You like French fries
But you don't like French fries
You've got socks on
But you don't have socks on
You're a girl, but you're a boy
Girl, boy, girl
Yes, no, yes, no, yes, no, yes, no, red, green
Red, green, red, green, red
She loves me, she loves me not, she loves me
She loves me not, she
from Mr. Hughes SaysTell your sister and your brother
Tell the alien and the chimp
Tell the corpse and tell the killer
Tell the pilot and the blimp
Tell the wind and tell the phone
Tell the birds and tell the fly
Tell the streetlights and the car
Tell the stars and tell the sky
Mr. Hughes says, "Live and learn.
Dig and be dug in return."
Tell the boxer and the fist
Tell the logo and the lid
Tell the ladies and the lords
Tell the goats and tell the kid
Tell the stylus and the disc
Tell the dust and tell the breeze
Tell the needles and the wool
Tell the locks and tell the keys
Even Numbers includes "girl/boy" among its examples of equal opposites: even/odd, red/green, take/skip, yes/no. "You're a girl but you're a boy" expects this equal-oppositeness to be so obvious that the listener understands it's flipping between addressing two different people, but that wouldn't be a given from a mutable-gender perspective!
Gender isn't completely irrelevant in this song about basic math; the "she" in "she loves me not" is presumably picked because we know that the singer is a "he". But it's still just the symmetry of the pair that matters; no point is being made about the gender of the action. It's easy to imagine that if sung by a "she", the lyric could be flipped to "he loves me not" with no sense of subversion or shift in meaning.
Mr. Hughes Says lists "ladies/lords" among asymmetrical pairs which not only act on each other, but often require the existence of the other to serve their purpose: pilot/blimp, streetlights/car, boxer/fist, stylus/disc, needles/wool, locks/keys. Many of these roles are not fixed opposites: goat/kid (and possibly alien/chimp, by 2001: A Space Odyssey logic) represent two stages of the same thing, and a killer can easily become the next corpse.
The chorus of "Dig and be dug in return" emphasizes the reciprocal relationships between these pairs. The idea that people serve different roles in a relationship according to their gender is strong, but isn't limited to a romantic context: "sister/brother" is another example used here.
One of the inspirations for the ideas on this page was listening to the Don't Let's Start fan podcast discussion (in eps 65 & 66) on John and John's torch songs, written in the 80s for the Watchface project "More Songs of Desire and Despair". These songs were written for singer Iris Rose, and they raise an interesting angle on gender: what does it mean to write/perform a love song for a "woman's point of view"?
Plain As The Lie On Your Lips by John Linnell
As Jordan Cooper rather recursively says, "Linnell's song is kind of like a Linnell song." I would agree: there isn't a strong difference in tone, lyricism, or delivery between the demo and final product... or between this and many of John Linnell's other Love Gone Sour songs. I might compare the themes or the delivery to songs such as Museum Of Idiots or Stormy Pinkness (both of which leave the narrator and addressee's gender undefined).
A familiar symbol for male/female relationships does appear here, the lock and the key; a more Freudian analysis might find meaning in the choice of female lock vs. male key. But in context, it's the cage and the entrapment that feels like the focus of the metaphor. The words "boy" and "girl" could easily be swapped, and the biggest casualty would be the three-way rhyme with "toy" and "destroy" in the bridge.
The gender-agnosticism here is strong enough that the DLS hosts switch (seemingly without noticing) to interpreting the lyrics as a man addressing a woman, even after catching themselves on that point during the bridge!
Don't I Have The Right by John Flansburgh
As Jordan says, "Flansburgh really transformed himself." Again, I would agree: both demos have put-on, decidedly gendered character-performance aspects. The hosts never confuse the gender of the point-of-view character when discussing these two songs, even when they're relating their personal experiences to the "female" version (or their wives' opinions to the "male" one.)
The sense that male and female experiences overlap without being 1:1 equivalent is expressed through changes in tempo, key, emotional temperature, and even main melody. The woman's lament "Never told me I'm pretty" becomes the man's disparaging "Never dressed up real pretty". The masculine character comes off as more flippant and entitled, likely as an observation of how sexist social structures encourage a man's sense that he has a "right to be loved".
Despite not being confused about either character's gender, Jordan stops to question if "we talked about rings" is 'really a line that a guy would sing'. In Dave's opinion, it is; the two men settle on it being a personal thing. Still, debating that question seems like a reaction to the Flansburgh-character effort to pick 'appropriate' words and actions for a gender role.