February 17, 2015 4:35 PM EST

There are few magazine-world traditions as instantly recognizable as the cover of the New Yorker, a space that’s only grown in prestige the further it moves from the actual contents of the magazine.

Most magazines use their covers to advertise a particular story within the issue, but the New Yorker—which is celebrating its 90th anniversary this week with nine different covers—uses its often-jokey covers to promote a general sensibility: Tuned-in but as often as not divorced from the news cycle, witty in an often absurd way, self-consciously erudite.

From the magazine’s first cover, which featured the foppish mascot Eustace B. Tilley, through editor Tina Brown’s announcing her buzzy presence with a cover depicting a Hasidic man kissing a black woman amidst racial tensions in Brooklyn’s Crown Heights, on to the recent era of sharply critical engagement with stereotypes around the Obamas and the misdeeds of Anthony Weiner and Chris Christie, the magazine’s cover has crystallized both the news and something more ineffable: The culture.

Here are some of the most memorable moments of artistic greatness from the New Yorker‘s history.

Contact us at letters@time.com.

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