On his second Elektra album, recorded at the Greenwich Village nightclub One Sheridan Square during the last week of 1960, monologist Jean Shepherd offers a mixture of hipster perspective and warm nostalgia. That can be a paradoxical combination, but he pulls it off to the delight of the audience. In "The Playboy Syndrome," for example, this transplanted Chicagoan captures the attitude of a typical New Yorker when he describes the U.S. as "that gigantic country, just clinging to this little island here." But soon after, he gives away his greater affection for Midwestern life, especially the life he lived in his childhood. Although he often has his audience in stitches, Shepherd, best known for his radio monologues, is not so much a comedian as a storyteller. "My First Blind Date" and "Little Orphan Annie" are both reminiscences that end in disappointment, but what makes them work is not the twist at the conclusion of the story so much as the descriptions. Approaching the home of his blind date, for example, Shepherd refers to it as "a kneeling home," giving a sense of its size in comparison to the "linoleum house" he himself lived in. And the material also works because of the enthusiasm with which Shepherd talks, even when he is speaking with a rueful admiration of an advertisement. The effect is not exactly satirical so much as it is critically affectionate. Shepherd's audience in the Village, primed by his radio work, warmly responds to that affection even at the end, when he seems to dismiss them on the edge of a new year.
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AllMusic Review by William Ruhlmann