We could ask the artists directly, of course. In interviews, Johns Flansburgh and Linnell have always expressed disinterest and disapproval in the sexist machismo that runs through a lot of rock culture. And since the late 2010s when it became a hot-button topic, the entire band has been been pointedly supportive of the transgender community. (The band's history of branding with THEY pronouns can't have hurt the gender-diversity of their following, either.)
We could also look through the Gender Issues theme on TMBW for how these beliefs might come through in their songwriting. But personally, I believe that even more interesting than an artist's intentional statements are their work's unintentional ones. This page is for musing on patterns I've observed between songs, considering how they might fit together to reveal underlying philosophies, occasionally diving into individual songs that provide particularly clear examples.
Many songs written by John Linnell are remarkably gender-agnostic: characters' genders could be swapped without much subversion or change in meaning. Grammatical gender often shapes these songs' lyrical structure without making much of a statement about social gender differences. Female and male characters are generally balanced in number and importance.
Linguistically, gendered pronouns are useful for differentiating unnamed people in a world full of male-female pairs.
Traditionally, but not necessarily, romantic couples. The pair's dynamic is often troubled, but it's only rarely and vaguely implied that the tension comes from any gendered difference:
Ultimately, most human flaws, goals, and anxieties are (or should be) universal across gender categories.
These songs frequently present a leveled playing field where a series of characters all represent the same experience or idea. Each new set of pronouns acts mainly as a bullet point for each new example:
*(We'll come back to places where this extends to nonhuman characters, with the neuter/inanimate "it" pronoun, in a later section.)
Women and Men is probably John Linnell's most immediately identifiable song "about gender". However, while the song divides the world into "women 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 actually more accurate to say that "woman" and "man" refer to sex category here: the strongest "gendered" declaration is that these pairings generally lead to sexual reproduction. But any social or even biological difference in roles in reproduction or child-rearing is left out as unimportant; that happens off in the jungle. While women and men were traditionally expected to serve drastically different roles when it comes to exploration or sea travel, that element, too, is ignored (or maybe corrected for).
The sex/gender of the person who sings this song is equally irrelevant. Ultimately, it's an observation on humankind's tendency towards migration and population growth, ignoring social factors in favor of simply focusing on the logistical necessity of both sexes in order for this ancient process to continue.
In many songs written by John Flansburgh, the experiences of men and women are much more visibly asymmetrical. Social gender helps describe characters' actions, plans, obligations, or role in a relationship. The ability to perform according to (or against) gender roles may be a conscious source of anxiety or pride.
Socially, gender describes actions that must be learned and titles that must be earned.
Performing gender takes effort! Characters in these songs may feel pressured, particularly in the world of romance, to prove that they deserve the "job title" of being a boy or man:
It's possible to play roles and earn titles that cross expected gender categories.
In these songs, these don't fully replace the character's sex-assigned gender, but stack on top without contradiction. It's mostly women who take on masculine roles for fun or empowerment:
Gendered action is often planned between people who share a gender category.
Characters in these songs may find special comfort and cameraderie in socializing with others who share their gender-goals, particularly when discussing romance:
How Can I Sing Like A Girl is probably John Flansburgh's most immediately identifiable song "about gender", and it is explicitly about performance anxiety.
The song depends on the idea that even outside the world of romance and reproduction, an action can be done "like a girl" regardless of the sex or even gender of the person doing it. This is decidedly not a symmetrical equation; the song's meaning would shift if we didn't see the singer as a man. The song recognizes that there's a unique insult inherent to the phrase "like a girl" (versus "like a man" or even "like a lady").
The song's title addresses the listener, seeking advice. "How can I?" isn't asking if it's possible to perform against type, but instead anxiously looking for help in getting away with it. The narrator wants to find community with those with shared gender-goals and never be alone: a social solution to this social problem.
These songs are an odd pair to compare—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.
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" in the male demo is 'really a line that a guy would sing'. In Dave's opinion, it is; the two men settle on it being an arbitrary personal thing. Taking the time to debate that question, though, feels like taking part in the very visible Flansburgh-character effort to pick 'appropriate' words and actions for a gender role.