EDITING THE NEW YORKER is a little like being a controlled demolitions expert. In both jobs, you are entrusted with valuable, long-standing structures and explosive material, and given the responsibility of ensuring that targets are properly selected, and that explosions leave no collateral damage. This characterization may raise the eyebrows of anyone who automatically dismisses the weekly magazine as a bastion of upper-middle class triviality, the home of tepid and watery poetry, cartoons bafflingly dependant on Manhattan coterie knowledge, short stories that obsessively focus on the minutiae of domestic life, and mildly left-of-center political and cultural commentary. The tradition of mocking The New Yorker for being safe and bourgeois has a long intellectual pedigree. In a 1937 essay in the Partisan Review, Dwight Macdonald lamented that the typical New Yorker writer “has given up the struggle to make sense out of a world which daily grows more complicated. His stock of data is strictly limited to the inconsequential.” A decade later, another Partisan Review stalwart, Robert Warshow, pushed Macdonald’s argument a step further by arguing that

The New Yorker at its best provides the intelligent and cultured undergraduate with the most comfortable and least compromising attitude he can assume toward capitalist society without being forced into actual conflict. It rejects the vulgarity and inhumanity of the public world of politics and business and provincial morality, and sets up in opposition to this a private and pseudo-aristocratic world of good humor, intelligence, and good taste.

Macdonald and Warshow were bracingly forthright critics, but they were only half-right in their assessment of The New Yorker’s banality. It is more accurate to say that The New Yorker, from its earliest days, has had a divided soul, being a prime example of the “bourgeois-bohemian” sensibility that Wyndham Lewis first dissected in his 1917 novel Tarr (many decades before David Brooks resurrected and vulgarized the concept in his 2000 essay "Bobos in Paradise"). To pigeonhole The New Yorker as a comfy cultural consumer item for moneyed liberals — tempting as it is — ignores the magazine’s long history of publishing abrasive and subversive works of art and reportage amid more wishy-washy fare.

From the start, The New Yorker has livened up its natural blandness with bohemian spice. In finding a tone for his magazine, founding editor Harold Ross turned to a surprising source: radical publication The Masses, an anti-capitalist outlet known for printing innovative cartooning and satire. From the ranks of The Masses, Ross acquired the services of such erstwhile rabble-rousers as Max Eastman, Otto Soglow, and Howard Brubaker. As cultural historian Kenneth Lynn once noted,

Rebels had served as the research and development wing of American society, and in the 1...