Paul Richmond: Painting Your Undies

In a world full of underwear models, skilled photographers, visual effects, makeup and more, pictures of guys in underwear are [generally] cut from the same cloth. It can be hard to find something truly unique. Paul Richmond, however, paints pictures of guys in underwear giving him a truly niche place amongst all the rest. Paul Richmond, who hosted his first solo show in 2007, recently caught our eye with his “Cheesecake Boys” collection of paintings. The gallery of artwork features over 20 men in their underwear; some of them models, some celebrities and some everyday guys as well.

Inspired by the pin-up girl art of the 1940’s and 50’s, Paul Richmond’s art has an innocence to it as well as an undeniable sexiness. In an exclusive interview, Paul tells us all about how he comes up with his ideas and how he decides what underwear to put on his painted men.

Check out our interview with the painter below, as well as more selections from his “Cheesecake Boys” gallery.

Underwear Expert: So, Paul, what would you say is your main inspiration for painting men in their underwear?

Paul Richmond: I’ve always loved pin-up girl art from the 40’s and 50’s – those crazy scenarios resulting in oh-so-titillating glimpses of a cheesecake girl’s undergarments. There’s something completely innocent and yet a little twisted about those paintings. I wondered why men were never depicted in the same way. Pin-up boys from that era – the beefcakes – sometimes showed us their skivvies too, but they were always in control of their sexy shenanigans. I thought if stray nails, gusts of wind, and other treacherous devices of fate could conspire to strip so many girls of their clothing, it should happen to men too! Plus, they always told us in art school to paint what we love.

UX: Many of your “Cheesecake Boys” simulate real celebrities and figures in their underwear such as Perez Hilton and Bobby Trendy. Is there a certain process behind deciding who wears what style, or is it totally up to you?

Paul Richmond: I’ve been lucky to collaborate with a whole host of fabulous celebs who graciously sacrificed their time (and their pants) for this series. In addition to Perez and Bobby, I also worked with Jack Mackenroth, Ari Gold, Mike Ruiz, Jesse Archer, James St. James, and a bunch more. I kick things off by brainstorming with them to dream up their perfect pin-up scenarios. Like the Cheesecake Girls, whose wardrobe malfunctions typically occurred during their daily routines of grocery shopping and cooking, I wanted the paintings to say something more about my subjects. Hence, Mike Ruiz is shown splitting his pants in the midst of a photo shoot and Ari Gold’s trousers take an untimely tumble during a concert performance. After we nail down their concept, the model poses for some hilariously incriminating reference photos. From there I will sketch it and add my own spin on things. Sometimes the undies shown in the paintings are exactly what they were wearing, and then there are cases where I take some artistic license because I think a certain color or style will work best for the image.

UX: A lot of underwear in the “Cheesecake Boys” paintings is shown in detail. Are there any specific brands or collections of underwear that you draw inspiration or guidance from when painting skivvies onto your boys?

Paul Richmond: I love the variety of underwear choices men have today. It’s not a tighty-whitey world any more, and that makes my paintings a lot of fun (and certainly more colorful!). I’ve painted a lot of different brands, and I’ve even made up underwear designs and styles of my own – especially some of the over-the-top patterned briefs I’ve used in my Christmas series. In fact, my dream is to one day develop my own line of men’s underwear with illustrated patterns. I love seeing my paintings hanging on a gallery wall, but seriously, what better canvas would there be?

UX: On your website you say that you really loved Barbie and Snow White as a child, and even set your sights on Disney Animation Studios. Do you try to incorporate any Disney or cartoon-esque looks into your art, or would you rather keep it more realistic?

Paul Richmond: I think a lot of my work, if taken in a slightly different context, could fit right into the storyline of an animated feature. Kids think underwear is hilarious! Think of all of the zany villains that get tripped up at inopportune moments by losing their pants to reveal gigantic heart-covered boxers! Of course my work is meant for a different audience, but humor and playfulness are certainly key ingredients. After all, sexuality can be silly and fun, and I don’t believe for a second that men have to be stoic in order to be attractive. Sometimes a pair of skivvies and a big goofy grin is the sexiest combo imaginable!

UX: And because we’re all dying to know, what’s the most fun part about drawing men in underwear?

Paul Richmond: I should probably say something like exploring the deep sociological undercurrents of gender identity and sexuality, but you would see right through that, huh? Honestly, dreaming up the situations is probably the most fun part. It’s not so uncommon to see men flashing their undies these days – I passed someone on the sidewalk earlier who was wearing his pants at about knee-level. But concocting whimsical, clever ways to get guys out of their clothes is a fun challenge that never gets old!

Check out some of Paul Richmond’s work below, and let us know what you think!

“Peeping Perez, Starring Perez Hilton”
“The Bear Tamer”

“The Strongman”


“Stop, Shop, and Drop, Starring Dale Levitksi”


“Dog Days”

Photo Credit: Paul Richmond

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