The Evolution of Men's Underwear

Scary chastity underwear. "The New Order" indeed.

Men's underpants can be both mysterious and confounding. Selling them in magazines obviously posed problems of context and decency. In an effort to keep things light, many ads ended up going to dark and fetid places. Places you should avoid. Other ads went deep into the wedgie of the double entendre, hopefully blindly. And some ads are simply fun to gawk over. Enjoy!

Inches? A nudist colony? Mild support? Looks like a locker room dust-up about to explode!

Really, Hank, you don't have to play the towel-snapping game now. No one else is here. As soon as I fasten this garter I am going to kiss you with great vigor.

Sometimes I like to light up a cigar and wash my underwear at night. I try to be in the moment.

Judd Hirsch's career was floundering a bit before the 'Taxi' gig.

Warning, white, when wet becomes transparent. But Sebastian didn't tell you that when he dragged you into the water with all those boys looking, did he?

Bob? Why are you out there in the middle of the night in your Munsingwear stretchy-seat underpants digging a ditch? Bob? I am asking you a question, Bob.

Mary mother of God, what is going on here?

My X-ray specs that I ordered in the back of that 'Archie' comic book work. But only sort of.

Show-off. All the boys can see your dirty pillows.

There is something terrible about to happen here with a flipper. Really terrible. And all the men are wearing Lilly Pulitzer skorts.

Just going to pass on this one, OK? The heavy lifting is already done here.

Bunny Bixler and I were in the semifinals

— the very semifinals, mind you — of the badminton tournament at the club and this ghastly thing happened. We were both playing way over our heads and the score was 29-28. And we had this really terrific volley and I stepped back to get this really terrific shot. And I stepped on the shuttlecock! I just squashed it to bits. And then Bunny and I ran to the closet of the game room to get another shuttlecock and the closet was locked! Imagine? We had to call the whole thing off. Well, it was ghastly. Well, it was just ghastly.

Have you ever seen a grown man's rapier, Timmy?

Sure, what could go wrong?

OK, fatigue from what? Hauling around the family jewels all day? Really?

Leave it to the Japanese to make the only not-weird underwear ad. Of course we can't read the copy.

Omigod, Bennet, doesn't it feel good to just light up and cross your fucking legs?

Boys! Boys! The only way this dispute can be settled is with a wrestling mat and some Wesson Oil!

No.

Oh, Leonard, let's just do something quite insane and take off all our quality undergarments and then ... switch! Sheer madness!

Get a room.

Perhaps you didn't know that Walt Disney had a side job as men's intimate wear model. With his son, Dizzy.

Take another photo, Danny, the first one had 2,073 likes on Facebook!