1. Andy Warhol – May 1969

A celebration of the Pop art movement, the cover featured Warhol being drop at a Campbell’s soup can. According to Lois, “When this article came up, I decided to show him drowning in his own soup. He knew it was just a friendly spoof on his original claim to fame.”

Jonathan Stone for Art-Sheep

George Lois was a genius graphic designer famous for his legendary covers of Esquire magazine. Satirizing and icon-shattering, these covers commented on important issues of the ’60s. Featured here you’ll see the most popular, controversial and delightful Esquire covers and their imaginative pictures.

2. Muhammad Ali as a Martyr – April 1968

Muhammad Ali poses as a martyr for refusing to fight in the Vietnam war and the cover becomes a protest poster hung in college dorms all over America

3. The Vietnam War – October 1966

The words on the cover were from an article written by John Sack, who reported on a U.S. soldier’s reaction upon discovering they had killed a Vietnamese child during a search-and-destroy mission.

4. Ursula Andres as a symbol for domestic violence – July 1967

Bond girl Ursula Andress posed as a symbol of domestic violence that was still a taboo topic at the time.

5. A satirical cover of Nixon – May 1968

Satirizing Nixon’s run up to the 1968 election.

6. Stewardesses – February 1964

One of Esquire’s biggest selling issues on the newsstands, it features forty stewardesses from fifteen international airlines.

7. Sonny Liston as “The First Black Santa” – December 1963

“All hell broke loose when the cover came out.”

8. An homage issue – October 1968

For its 35th anniversary, Esquire featured JFK, Robert Kennedy, and Dr. Martin Luther King Jr. on its cover, watching over Arlington National Cemetery, like a “dream-like epitaph on the murder of American goodness.”

9. Claudia Cardinale – December 1966

10. A Truman Capote cover – December 1967

Commenting on Truman Capote’s infamous 1966 masked ball when he invited 540 of his closest friends!

11. The face of a hero – September 1965

A composition of all four leading heroes for every American college student of the 1960s, Bob Dylan, Malcolm X, John F. Kennedy, and Fidel Castro, creating the “Ultimate American Hero”

12. American kids growing up – May 1967

The incident as headlined on the cover was “the moment when an all-American kid started to grow up with live violence in his carpeted den, complete with an all-American hamburger and Coke,” according to Lois.

13. The masculinization of the American woman – March 1965

“Was there a point where sexual equality would end and confusion begin?” wondered Lois, influenced by the slowly growing feminist movement. Italian actress Virna Lisi posed for the cover.

14. The fashionable cover – October 1963

15. JFK several months after his assassination – June 1964

According to Lois, it “…showed the opposite symbolism-of Kennedy himself, crying for his lost destiny.”