When considering the art of any given issue of The Observer — a motley collection of photos, illustrations and whatever else we can think to squeeze inside our pages—one piece weighs heavier than all others. The cover.

Besides all the usual concerns common to any publication (newsstand sales, “making it pop”), part of that weight comes from our distinct history with cover art. As The Observer came into its own in the ’90s, a poker and prodder and jovial court-jester-cum-chronicler of the city’s cultural elite, we set ourselves apart visually by leading our covers with caricatures and illustration.

“During a period when current-affairs caricature had few outlets,” wrote noted design historian Steven Heller in a 2009 Print magazine article, “the Observer was an oasis.”

It continues to be so today. The strategy allows us to be a little chummy and fun, while still skewering those powerful characters who populate our city. The idea was not merely to illustrate a story, but to evoke some nuance that took the story beyond the black-and-pink of the words on the page.

Most of the images above are by four artists, who worked as a rotating cast through the majority of our history: Philip Burke, Drew Friedman, Robert Grossman and Victor Juhasz. In recent years, that list has expanded, but the reasoning behind our cover art remains the same.

It’s not The Observer if it’s not pink. And it’s not The Observer if it doesn’t lead with an illustration.

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Credits:

Steve Jobs by Robert Grossman

Monica Lewinsky by Robert Grossman

Norman Mailer by Drew Friedman

George W. Bush et al. by Robert Grossman

Popeye McCain by Drew Friedman

Woody Allen and Larry David by Philip Burke

Gay Talese by Philip Burke

Conan O’Brien by Drew Friedman

Woody Allen with Knick by Drew Friedman

Hillary Clinton by Philip Burke

Dick Cheney and Bloomberg by Drew Friedman

Big Bad Rupert Murdoch by Victor Juhasz

Madame Bloomberg by Robert Grossman

Monica Lewinsky and Bill Clinton by Drew Friedman

McCain and Obama by Drew Friedman

Osama bin Laden and CNN News Crew by Robert Grossman

Daniel Libeskind and David Childs by Robert Grossman

Luminaries at Elaine’s by Drew Friedman

Bloomberg and Murdoch by Jason Seiler

Jerry Seinfeld by Philip Burke

Charles Rangel by Dale Stephanos

Occupy Wallstreet-ers by Zina Saunders

Harvey Weinstein, Rudy Giuliani and Robert De Niro by Drew Friedman

2013 Mayoral Candidates by Victor Juhasz

Anthony Weiner by Drew Friedman