In case you missed it, Jack Klugman died on Christmas Eve at the age of 90. The actor was beloved for his high-profile television roles, but I always most adored Klugman as an archetypal New Yorker (even if he was born in Philadelphia, died in California, and filmed The Odd Couple in LA): there was something rumpled-hatted about him even when he was cleaned up; he looked like he’d had a few even when he was sober. He was the personification of “urban” in the old-fashioned sense—of rainy streets, fedoras, night clubs, loneliness. Klugman was like a character out of an Edward Hopper painting or a Frank Sinatra song. Here are some of his best roles that exemplify that.