Cover of Esquire (March 1952)

Esquire Magazine

Esquire is an American men’s magazine founded in 1933 by Hearst Communications. It flourished during the Great Depression and World War II and has more than 20 international editions. Syd contributed over 300 cartoon spanning nearly four decades from 1934-1968.

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Businessmen discuss dissolving partnership.

"Let's dissolve partnership, Max. I'm sick of dividing two into nothing every week." (May 1934)

Black and white cartoon of baseball players arguing.

"But I could have sworn it was a strike." (July 1934)

Man in bed with doctor and woman.

“For my part he can drop dead, Doctor. I begged him to wear rubbers” (Feb. 1935)

Angry mother yelling at son to wake up as father looks on

“Get up, you dirty aristocrat!” (Jan 1935)

Witness is sworn-in at trial

"– – so help me God!" (July 1935)

Father complains to wife about daughter

“For the last time—tell her to stop psychoanalyzing me!” (July 1935)

Woman laments alone on fire-escape as distraught husband looks on from within

“O, Romeo, wherefore art thou, Romeo?” (July 1935)

Black and white cartoon of a man giving a trophy to a woman.

"The landlord sent this, Mrs. Kantor. You’re the only tenant that pays her rent" (Oct. 1935)

Santa tells woman he'll be back at six.

"I'll be through at six, babe!" (Dec. 1935)

A man stopped by a police officer in a tank.

"I got it for Sunday driving, Officer" (June 1936)

Two prisoners in jail talk about a bank robbery.

"So you robbed the bank—well, glad to meecha, I'm its founder!" (July 1936)

Cartoon of two police officers and a violin case.

“It is a violin!” (Sep. 1936)

Woman teaches her kids traffic safety (Esquire Feb. 1937)

“Always wait for the red light—then if you get hit you can sue” (Feb. 1937)

Boy wakes sleeping father with a hammer.

"No, Junior! It’s Sunday morning—wake papa up gently" (Apr. 1937)

Two fencers clash during a lesson.

"That's the sort of thing we're trying to discourage" (May 1937)

Two men in hammocks on a ship.

"It's your turn to sing me to sleep!" (June 1937)

Black and white cartoon of a couple embracing.

"With my eyes shut, Meyer, I wouldn't know you from Gable" (Dec. 1937)

Two men on raft, one pointing.

"Let's paddle—who knows, there may be two gorgeous shipwrecked blondes over yon" (Sep. 1940)

Suitor argues with girl's father

"Did you ever stop to consider that perhaps I'm the best she can do?" (Apr. 1950)

Cartoon of a woman in a cake at a wedding.

"OOPS! Wrong party!" (Apr. 1950)

Man in coat whispers to book seller.

"Suppressed Book-of-the-Month!" (Nov. 1950)

Father confronts smooching boyfriend

“I don't mind your kissing my daughter, but would you mind not pressing her against the bell?” (Feb. 1951)

Cartoon of couple on flooded rooftop.

"How can you think of such a thing at a time like this?" (Apr. 1951)

A cartoon of a dentist tying up a patient.

"Just relax—this isn't going to hurt a bit." (May 1951)

Freshly engaged woman tells-off ex on phone (Esquire, vol. 37, no. 1, Jan 1952)

“Hello, Peter. You can go to hell now” (Jan. 1952)

Cartoon of mechanic asking for bill.

"Okay, Andy, bring the gentleman his bill" (Apr. 1952)

A mother lectures her daughter (Esquire, May 1952)

"At your age, Louise, I was living it—not reading it." (May 1952)

Defendant pleads with judge in courtroom.

"How about making it 40 or nothing, Judge?" (June 1952)

Wife recalling a dream or her husband as a young suitor?

". . . then he reached down from his white horse and swept me into his arms" (Feb. 1953)

Man disappointed saloon closed on Tuesdays.

[Palace Saloon – Closed Tuesdays] (Mar. 1953)

Couple in run-down apartment sitting at kitchen table, husband with newspaper griping.

"I never promised you gracious living." (May 1953)

Jurors losing their patience with a hold-out

"Oh, for heaven's sake, forget the evidence and think for yourselves!" (Aug. 1955)

Black and white cartoon of a couple arguing.

"You want to make up already? Give me a break—you only got angry two days ago!" (Jan. 1956)

Man holding fabric, showing customer DIY suit.

"Now, here's the very latest in low-overhead tailoring—a do-it-yourself suit" (Feb. 1956)

Handwriting expert working at suggestion box.

"This is Mr. Simmons, a handwriting expert; he'll be working here a few days. In the meantime, all of you go right on dropping notes in the suggestion box!" (Mar. 1956)

Baseball player returns to dugout.

"I love his hustle-notice how quickly he gets back to the dugout after he strikes out." (May 1956)

Black and white cartoon of a driving school.

"I'm a parking-lot attendant—some of the night customers are chipping in for my course" (June 1956)

Man staring at a pinup while wife irons his shirt

“Why don’t you ask her to iron your shirts for you?” (Jan. 1957)

Woman asks man how he wants his argument.

"How do you want your argument this morning?" (July 1957)

Smaller drunk asks larger drunk to step outside a bar.

"When I told you to step outside and say that, I didn't mean I was coming with you!" (Jan. 1958)

Man at the IRS with income tax forms.

"Money! Money! Money! That's all you ever think about!" (Apr. 1958)

Man tells wife about hot golf round.

"Went around the course in ninety-five today—that was the temperature, you undertand" (Aug. 1958)

Cartoon of a couple arguing about taxes.

"Don't you dare list me as a dependent!" (Oct. 1958)

Cartoon of man carrying woman in water.

"Don't do that again, Mother. . . I promise to write you more often" (Oct. 1961)

Husband's advances rebuffed (Esquire Nov. 1961)

"Please, John, don’t ruin a wonderful evening!" (Nov. 1961)

Cartoon of a man bowing to a woman.

"I yield to the Speaker of the House" (Dec. 1961)

Prison guard tells visitor bad news.

"He said to tell you he was hanged this morning." (Jan. 1962)

Cartoon of people reacting to doomsday.

"So long, Gus, see you tomorrow!" (Mar. 1962)

Doctor gives woman prescription for sleeping pills

"Your husband needs peace and quiet. I want you to take one of those sleeping pills every night before he goes to bed" (May 1962)

Man on phone in locker room cartoon.

It's the cereal company... they want you to say you don't use their product" (June 1962)

Fortune teller reads man's future.

"Who was that lady I saw you with tomorrow night?" (July 1962)

Woman in robe yells at her reflection.

"You lie!" (Dec. 1962)

Couple on beach, man looking away.

"I wish you'd look at me when you talk!" (Mar. 1963)

Man on phone interrupted at dinner.

"Who shall I say is interrupting my dinner?" (Aug. 1963)

Couple in marriage counseling session.

"How long has it been since you swept her into your arms and told her she's beautiful?" (July 1964)

Cartoon of parents yelling at son.

"William, don't your own parents mean anything to you?" (June 1965)

Cartoon of a dad meeting his daughter's boyfriend.

"Well, Dad, how do you like him?" (Apr. 1968)