Top 5: James Kaplan

Writer James Kaplan of Hastings-on-Hudson, whose work has appeared in the New Yorker, the New York Times Magazine, Vanity Fair, and New York, has just written a biography of legendary crooner Frank Sinatra simply titled Frank: The Voice. Here, the author chooses five of his favorite songs by the incomparable Ol’ Blue Eyes.

Photo by Erinn Hartman

“Night and Day” This 1942 recording of the great Cole Porter song was made when Sinatra was still with the Tommy Dorsey Orchestra. “Note the beautiful diction—the crisply separate Ds of ‘and’ and ‘day,’” Kaplan says. “But, especially, note that gorgeously yearning Sinatra voice.”

“Day In-Day Out” Sinatra actually recorded this Johnny Mercer/Rube Bloom love song three times with three different arrangers over the course of his career. Kaplan’s favorite version? The 1954 arrangement by the renowned Nelson Riddle. “It is, quite simply, one of the sexiest tunes ever recorded,” he says.

“Here’s That Rainy Day” Recorded by the singer in 1959 with a lush string arrangement by Gordon Jenkins, this, says Kaplan, is the greatest song crafted by Johnny Burke and Jimmy Van Heusen, its lyricist and composer, respectively. “Everyone should care about this magnificent number—one of the monuments of the American popular song.”

“The Tender Trap” Kaplan describes this song as a “lightly satirical, pre-politically correct hymn to marriage.” It is, he says, a prime example of the upbeat body of work created by Sammy Cahn and Jimmy Van Heusen for Sinatra that “emphasized his well-deserved image as a ring-a-ding-ding swinger.”

“The Best Is Yet to Come” Carolyn Leigh and Cy Coleman crafted this great number, which Kaplan describes as “an infectious yet moving finger-snapper of a love song, filled with optimism,” In 1964. But Coleman’s clever chord modulations, Kaplan notes, make this the most difficult Sinatra tune for amateurs to croon in the shower.