10 of the Funniest American Essayists of Our Time

Like many of you, this week we were saddened to hear of the death of phenomenal and darkly comic essayist David Rakoff, who had been battling cancer for many years. To celebrate his life and the great literature he left us with, we’ve put together a list of some of the funniest modern essayists, who like Rakoff, are following in the giant footsteps of Mark Twain, Dorothy Parker and James Thurber as America’s great humorists. We’ve tried to limit ourselves to purely contemporary writers, but since we’ve lost several hilarious and essential voices all too recently, we’ve cheated just a bit. Read through our list after the jump, and since these are only our personal preferences plucked from a very long list, be sure to add your own favorites in the comments.

David Rakoff

Rakoff was probably the most melancholic comedy writer of this or any time, his essays often as charmingly cranky as many of his peers’, but laced with a deeper, if lightly applied, sadness that made even the funniest hit home, especially when he wrote about his real life struggles with cancer. As Hilton Als reflected at Page-Turner, “[Rakoff’s work] combined the best aspects of reporting—a gimlet eye and an open heart—with a philosophical point of view that skipped ahead of any claim of self-indulgence.” He will be missed.

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