Take his entry on Billy Strayhorn’s bitter, lovely, transcendent “Lush Life” (1936). It’s clear from Gioia’s out-on-a-limb encomium (“If I were allowed to steal a single song from the twentieth century and make it my own, without a question it would be ‘Lush Life’ ”) that he grasps the singularity of Strayhorn’s triumph (a triumph achieved before the composer was 21), and his characterization of that triumph—“the sheer audacity of … a love song that denounces romance with such vehemence”—is at once spot-on and as eccentric as the song itself. For his handful of recommended recordings, he naturally enough lists the classic covers, the most famous of which are John Coltrane’s two versions, including his celebrated (and to my mind overpraised) recording with the singer Johnny Hartman. But Gioia also astutely selects Carmen McRae’s relatively obscure rendition, one of the finest vocal versions, and in fact rightly elevates it above the far-better-known versions by Ella Fitzgerald and Sarah Vaughan. Moreover, with great discernment he singles out Stan Getz’s brief, understated, overlooked recording.

VIDEO: Benjamin Schwarz shares some of the greatest jazz recordings of all time, from Frank Sinatra to Billy Strayhorn.

Still, the most impressive aspect of the entry is Gioia’s assessment of a single word. Strayhorn was openly homosexual, a fact that has led many commentators to somewhat reductively define him as a gay composer, and to congratulate themselves on their knowingness by seizing upon the first lines of “Lush Life” (“I used to visit all the very gay places”) as evidence of supposedly hidden messages in his work. But in a sensible, mild, elegant corrective, Gioia, who studied English at Stanford and is undoubtedly familiar with William Empson’s Seven Types of Ambiguity, observes:

Scholars have debated the semantic resonance of the term “gay” back in the Great Depression … In a song already rich with multiple meanings—even the title “Lush Life” can be taken two ways—the hypothesis that a coded additional level of signification resides in the lyrics cannot be resolved with any finality; yet even if Strayhorn intended this, I suspect he also felt confident that his song lost little in its overall impact when heard by audiences who missed the innuendo.

This perforce thumbnail appraisal of the song can’t match the depth and sophistication of the definitive analysis—Friedwald’s 23-page chapter devoted to “Lush Life” in Stardust Melodies (in which Friedwald amply proves his thesis that “it’s hard to think of another piece of music that has anything at all in common with ‘Lush Life’ ”). Yet Gioia’s entry, in its own way definitive, is but one of a quarter-thousand assessments in this monument to taste and scholarship.

To be sure, in any compilation like this one, the reader is bound to quarrel with the selection of some items and to bemoan the exclusion of others—and I question Gioia’s neglect of four songs in particular. All are pop songs of the period, written by white composers, that began on Broadway or Hollywood but acquired new, and much longer, life by having been played, and importantly transformed, by jazz musicians both black and white. The first is Richard Rodgers and Lorenz Hart’s “Where or When.” The finest version of that song, and among the earliest—the pared-down recording that Peggy Lee and the Benny Goodman Sextet made in a New York studio on Christmas Eve 1941, barely two weeks after America entered the Second World War—speaks to the quavering uncertainty of that historical moment and remains, for me, the most poignant jazz record ever made. Surely that rendition, along with the versions by Artie Shaw, Clifford Brown, Ella Fitzgerald, Sonny Rollins, Sinatra with Count Basie, and, more recently, the too-often unnoticed Tierney Sutton have earned the song an important place in the jazz repertoire. The same goes for three Cole Porter compositions: “In the Still of the Night” (recorded by Charlie Parker, Billy Eckstine, Charles Mingus, Miles Davis, and Oscar Peterson, among many, many other jazz musicians of the first rank), “Begin the Beguine” (Artie Shaw’s version is among the most popular records in jazz history; Django Reinhardt, Parker, Dizzy Gillespie, Coleman Hawkins, and Erroll Garner also recorded it), and “I’ve Got You Under My Skin” (important covers include those by Cab Calloway, Parker, Clifford Brown, Stan Getz, Bill Evans, and Earl Hines—and of course, Sinatra’s is one of the most swinging recordings ever produced).