Leyendecker Paintings Ranked by How Bad They Make Me Want To Move to a Mansion by the Sea With My Boyfriend And Throw Extravagant Parties

Let’s talk about J. C. Leyendecker.

One Mr. Joseph Christian Leyendecker.

Specifically, how his paintings make me feel a sort of way.

If you know J. C. Leyendecker at all, it’s probably from his iconic image of the Arrow Collar Man who defined American masculinity for decades.


Perhaps you have seen him in a poster (left) or that brief moment he showed up in The Great Gatsby (2013) directed by Baz Luhrmann (right)

Yes, the Arrow Collar Man is certainly attractive, but is that all I have? Oh no, gentle reader, that is not. It gets better.

What if I told you that the Arrow Collar Man was a real person, Charles Beach?

What if I told you that the Arrow Collar Man, Charles Beach, that bastion of American Heterosexual Masculinity, was J. C. Leyendecker’s longtime lover?

And they were known for throwing extravagant yet elegant parties.

In a mansion by the sea.

Specifically this mansion:


You would be wholly appreciative of the position J. C. Leyendecker’s paintings put me in, wouldn’t you?

So, without further delay, on to the paintings, rated purely by their ability to throw me into full-blown, flapper-infused hallucinations replete with Jazz Age soundtrack.



The men watch each other watching and there’s a tension in the space between their gazes. As much as the figures crowd each other, each remains alone. The overall composition suggests fleeting association, without background or context to ground the image — You can often feel lost in the hustle and bustle of modern life. Although you’ve caught the eye of the dandy to your right, he’s just another one of those smooth-talking boys who never stay. The city, the lights, him: that’s not what you need, you know it. You long for true companionship and a place apart from it all.

Rating: Moderate, but things are just getting warmed up.



The studied book. The monocle looped lazily around a finger. The ROBE. This has all the makings of gay malaise. You know it, I know it. It’s only a shock that literally the entire 20th century overlooked it — The evening is dark and the candles have burned low upon the mantel. Restless nights are consumed by the deafening quiet of the house and you read, but only in the most perfunctory way. Your eyes graze the words while your mind is elsewhere. You pine for the day you will meet him. But oh boy do you pine in style. 

Rating: Yep, we’re getting closer. I can see the contours of life coming into focus: the quiet nights, the dinners, a view of the sea through plate glass.



Gone is the tension and isolation of the earlier scenes, replaced by the comfortable recline of easy conversation — He’s in the common room and you begin to talk. Soon you learn he’s on the golf team, freshly returned from practice. You pick up a club and examine it. As the conversation lulls, you make some comment that betrays your deep ignorance of the sport; you can’t help it, you just want him to like you. Embarrassed, you try to pass the club back, but he tells you to hold onto it. He’ll meet you at the range tomorrow.

Rating: The downpayment on the mortgage has been made and I am currently loading up our vintage roadster with matching luggage cases.


Winyan Soo Hoo

This painting is what Dark Academia dreams are made of — You and your boyfriend sit in the study at night, him reading the day’s newspaper in an armchair while you assume a rakish position on the desk because why not. You begin to leaf through the pages of a book you have resolved to finish, looking for your place. He finds a particularly interesting article in the paper and asks to read it aloud. You oblige him. He does this every night, but you know he loves to and so you let him read on. Your book can wait. Oh the domesticity of it all!

Rating: The gardens have been immaculately manicured, the glasses are filled with Champagne, and we peer out the window into the darkness, waiting for the headlights of our guests to crest the hill.



To come down from the high of fantasizing about living the life of a queer and emotionally-fulfilled Jay Gatsby for just a moment, this painting is the realest shit.

I’ve never particularly liked playing golf, but after seeing this painting, I have never wanted to do something more in my life. Not to play the game itself, but to have the promise of a day spent out together, sealed with a glance. That’s where the heart of this painting lies, it’s in the glance, the sureness of it. The clubs they hold look almost like half-forgotten props in the drama of their shared connection. The painting captures a golden afternoon of endless possibility.

But, as is too often the case with queer life and love, history is harsher than we hope. Following the Stock Market Crash of 1929, the demand for paintings of Definitely Not Gay™ men dried up, crippling J. C. and Charles’ finances. Leyendecker also became increasingly reclusive in the final few decades of his life. Norman Rockwell, a huge Leyendecker fanboy, claimed it was all Beach’s fault (for this opinion I will now forever be suspicious of Norman Rockwell, a shame). Others said it was caused by the untimely death of Leyendecker’s younger brother, Frank. Either way, when J. C. died in 1951, and Charles soon after, things looked grim. 

Will that stop me from daydreaming about living with my boyfriend in our mansion by the sea where we throw extravagant yet elegant parties? Certainly not. But reality hems the fantasy conjured by Leyendecker’s paintings. An imagined queer past lived in richly painted hues is near intoxicating, but the quiet transgression of J. C. and Charles’ actual life together, despite its tragic notes, represents something fiction cannot provide.

The glance shared by the figures is sure, but it also suggests something else: this is a stolen moment. The woman’s momentary distraction creates space for the locking of eyes and the communication of things that cannot be said aloud. J. C. and Charles lived and died in a society that, despite idolizing the Arrow Collar Man, denigrated his creators. Yet even a life lived in stolen glances can have its golden afternoons and so, perhaps, we too can weather society’s scorn and, someday, find our own mansions by the sea.

Rating: I. Am. Ready.

2 thoughts on “Leyendecker Paintings Ranked by How Bad They Make Me Want To Move to a Mansion by the Sea With My Boyfriend And Throw Extravagant Parties

  1. ED says:

    #4. This fellow looks so very, very much like the archetypical escapee from Oscar Wilde that I have dark suspicions he’s actually a rambunctious heterosexual adopting protective colouring to throw off all those angry husbands …

    #1. I’m deeply amused by the fact that my only impression from this piece was “Such a nice doggy! Such a pal!” (I keep having to remind myself that there are four people in this particular illustration, which may say something about my mindset).


  2. ED says:

    Well, three people and a dog, strictly speaking – I have no objection to a dog being treated as a family member, but LOATHE seeing them babied.


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