Commentary Magazine

The Great American Songbook: A Critical Guide

Of America’s many contributions to the arts, the most widely influential—perhaps even more influential than jazz—may ultimately prove to be the body of popular song created during the 20th century by the commercial composers and lyricists who worked on Broadway and Tin Pan Alley and in Hollywood.

The men (and a few women) who wrote these songs did not exist in a cultural or artistic vacuum. Their work was rooted in a well-known European tradition—that of light opera, or operetta. But it was from the outset distinctively American in tone, colored not only by ragtime and early jazz but also by the pungent accent of what H.L. Mencken called “the American language.” Though a few European-born musicians, including Kurt Weill, have functioned successfully in the American idiom, no European could possibly have written the words or music of such songs as “Alexander’s Ragtime Band,” “Blues in the Night,” “I Got Rhythm,” or “You’re the Top.”

Three decades ago, however, when rock-and-roll appeared to have achieved complete cultural dominance in America, it was by no means a foregone conclusion that these and other songs by (respectively) Irving Berlin, Harold Arlen, George Gershwin, and Cole Porter would have remained popular to this day. Nor was that impression altogether wrong: pre-rock American popular song is no longer “commercial,” at least not in the way it was prior to 1960. With rare exceptions like Diana Krall’s recent recording of Burt Bacharach’s “The Look of Love,” one no longer hears such songs on the radio, or sees them performed on TV

But they do continue to be performed in concert and recorded regularly, not only by singers who first came to prominence in the 1940’s and 50’s but also by a new generation of younger artists, including Krall and John Pizzarelli. And while rock and its related idioms continue to dominate commercial music, more and more younger listeners are becoming interested in what James T. Maher has called “the professional tradition in song writing”—a tradition that continues to be carried on by such contemporary songwriters as the jazz pianist-singer Dave Frishberg.1



Oddly Enough, there is no universally accepted name for the fruits of this tradition, though they are occasionally referred to by the unwieldy title of “the great American songbook,” with the constituent entries known as “standards.” But with or without a name, most listeners know a standard when they hear one, and they also sense that there are fundamental differences in kind between songs arising from this tradition and those written by rock, blues, or country musicians.

The most significant of these differences is that standard songs are compositions. That is, their music exists in a definitive, fully written-out version, usually (but not always) prepared by the composer and published as sheet music. This is not typically true of rock songs, whose “definitive” form is a recording of a particular studio performance. In rock, song and performance can be difficult to differentiate; in pre-rock popular music, by contrast, the song is a pre-existing entity that can be performed by anyone. That is why the best such songs have coalesced over time into a canon, an oeuvre from which any performer can draw.

This is not to say that performers of standards strive to sing them exactly as written, in the way, say, that a classical singer performs an art song. To the contrary, each performer, working in tandem with an accompanist or musical director, creates his own arrangement, which may be sung more or less “straight” but always with a premium on interpretative individuality. But this is the paradox of the standard: precisely because it is fully notated and has a definitive shape, one can deviate widely from that shape without undermining the song’s essential identity. Tony Bennett, Judy Garland, and Frank Sinatra sing “The Man That Got Away” very differently, but there is no question that they are singing the same song.

Not only are standards compositions, but nearly all of them conform to a rigid structural pattern, in which an introductory verse is followed by a 32-bar chorus that falls into four eight-bar phrases. The chorus works like this: the first of the phrases is repeated, then there follows a contrasting phrase, then there is another repetition—not always exact—of the first phrase. (This structure is known as AABA form, with the B strain called the “bridge” or “release.”) The results are as simple and elegant in shape as a sonnet.

The lyrics of standard songs are similarly “classical” in design. The first generation of writers patterned their work after 19th-century light verse, with its often quite elaborate rhymes and scansions.2 Most of these writers, particularly Ira Gershwin, Lorenz Hart, and Cole Porter, attained a high degree of verbal dexterity, which is one reason their work was so immediately memorable. Yet their subject matter was not normally comic: most standards are love songs, and while a good many are light in tone, even more are perfectly serious and sometimes deeply felt.

As this brief description suggests, standard songwriters were self-aware craftsmen-professionals, to use James Maher’s term. This again marks a difference from rock-and-roll: there the craft is more likely to go into the performances than into the songs, which often contain semi-improvised elements and in any case rarely have the technical finish of a standard. It is especially unusual to encounter a rock song whose lyrics employ the elaborate rhyme schemes commonly found in the work of, say, Hart, Porter, or Stephen Sondheim.



No less distinctive than American popular song is American popular singing. It is infinitely varied in style—from the lightness and grace of Fred Astaire to the intense inwardness of Frank Sinatra—and just as deserving of serious critical consideration. In fact, it is hard to separate the two, for the best singers have usually sung the best songs, and it is by their performances that we know those songs.

Partly for this reason, and partly because the number of first-class standards is unmanageably large, any effort to draw up a list of the finest American popular songs is bound to come to grief. In attempting nevertheless to do justice to the subject, I have chosen to approach it from another direction. What follows is the first installment of an alphabetical list of 50 American pop singers of the 20th century, each one performing a different song, all of them currently available on CD.

This list is neither comprehensive nor objective, but it is also not arbitrary. Above all, it reflects my own taste. These are, quite simply, some of the songs I like best, and most (though not all) of the singers. No attempt has been made to include singers primarily active in other countries (like Al Bowlly or João Gilberto) or songs originally written in other languages (although Antonio Carlos Jobim, Brazil’s greatest songwriter, is included, Brazilian music having been absorbed into the culture of American pop and jazz).

The list is arranged by singer, but it is primarily about songs, and so certain well-known jazz and blues singers are absent. In some cases this is because they are less interested in interpretation than in improvisation—a legitimate preference, but one which tends to obscure the unique qualities of the songs they sing. In other cases it is because my view of their work is at variance with received opinion. Finally, I have not sought to include every well-known standard; although there are many popular favorites here, I have been more interested in suggesting the extraordinary stylistic richness of standard songs and their interpreters.



1. Karrin Allyson: “Some Other Time.” Music by Leonard Bernstein, lyrics by Betty Comden and Adolph Green.

Except for Kurt Weill, Leonard Bernstein is the only serious classical composer to have successfully “crossed over” to the world of popular music, and four of his five musicals—On the Town, Wonderful Town, Candide, and West Side Story—continue to be revived. A half-dozen of his songs have become standards, including this wartime ballad from On the Town, which contains an unusual change of key at the bridge that reflects Bernstein’s classical training. The gentle lyric is by Betty Comden and Adolph Green, who appeared on stage in On the Town and went on to have a long partnership on Broadway and in Hollywood, writing both lyrics and scripts (among their best-known collaborations is the screenplay of the film Singin’ in the Rain).

“Some Other Time” was recorded in 1960 by the jazz pianist Bill Evans, and subsequently became popular among jazz singers. It is beautifully performed by Karrin Allyson, one of the few postwar jazz musicians to have won national recognition without living on the East or West Coast (she was still based in Kansas City when she made this recording). An imaginative improviser with a slender, sunny mezzo-soprano voice, Allyson points up the wistfulness of Bernstein’s wide-ranging melody (Azure-Té, Concord Jazz CCD-4641).



2. Louis Armstrong: “How Long Has This Been Going On?” Music by George Gershwin, lyrics by Ira Gershwin.

Most people think of the Gershwin brothers first whenever they think of American popular song. George combined classical clarity with the vitality of jazz to create a body of songs unrivaled in their consistently high quality, while the witty detachment of Ira’s elegantly crafted words virtually defined the art of lyric writing for a generation. “How Long Has This Been Going On?” is one of Ira’s more direct statements, and the deftly balanced phrases of George’s melody (pivoting on a flattened “blue” third) add expressiveness to the charming lyric.

Though better known as a trumpeter, Louis Armstrong also ranked among the most influential singers in the history of popular music—the first major jazz musician to show how a singer could improvise with as much swing and sophistication as an instrumentalist. As his trumpet embouchure deteriorated and his gravelly voice deepened in middle age, he began to devote more time to singing standard ballads, and this lovely performance from 1957, accompanied by the Oscar Peterson Quartet, is a delightful reminder of the deftness with which he could negotiate a tricky lyric (Let’s Do It: Best of the Verve Years, Verve 314 529 017-2).

3. Fred Astaire: “Cheek to Cheek.” Music and lyrics by Irving Berlin.

No popular songwriter was as stylistically diverse, or as commercially successful in so many media, as Irving Berlin. In addition to the free-standing songs of his Tin Pan Alley youth, he wrote with unfailing effectiveness for films and stage revues. When Richard Rodgers and Oscar Hammerstein II introduced the modern musical comedy, with its plot-driven, “integrated” songs, Berlin responded with Annie Get Your Gun, which contained more hit tunes than any other show in Broadway history. A musical illiterate—he could play piano only in the key of F-sharp and employed trained assistants to transcribe his work—he was nonetheless capable of producing such startlingly original songs as “Cheek to Cheek,” a 64-bar tune in AABBCA form. (Berlin also wrote his own lyrics, which were simpler than those of such virtuosos as Ira Gershwin but also more emotionally straightforward.)

“Cheek to Cheek” was written for Fred Astaire, a peerless theatrical dancer whose singing—about which he was famously modest—won him the admiration of countless songwriters. Despite the wispiness of his light tenor voice, he phrased lyrics with the same graceful touch he brought to his dancing. This studio recording, made in 1935 around the time of the filming of the movie Top Hat (in which “Cheek to Cheek” was introduced), is one of the best documents of Astaire’s singing in its prewar prime (A Portrait of Fred Astaire, Gallerie GALE 414).

4. Mildred Bailey: “St. Louis Blues.” Music and lyrics by W.C. Handy.

The traditional blues, with its lowered thirds and sevenths and twelve-bar AAB form, remains central to the jazz tradition a century after its emergence. It has also had a powerful influence on many American popular songwriters, though comparatively few have written “true” blues songs, and fewer still of these have become standards. An exception is W.C. Handy’s “St. Louis Blues,” a twelve-bar blues with a contrasting sixteen-bar, bridge-like strain set against a tango-based rhythm. Published in 1914, three years before the first jazz recordings were made, “St. Louis Blues” quickly became and has since remained one of the best-loved of all American popular songs.

Many jazz and blues singers have recorded “St. Louis Blues,” often to striking effect. This performance is by Mildred Bailey, a once-famous popular singer of the 1930’s whose recordings were largely forgotten after her death, though she is currently undergoing a critical revival. An unhealthily obese woman with a delicate, high-pitched voice and a distinctively shivery vibrato, she was one of the most creative jazz singers of her generation. On this lightly swinging performance from 1939, she is accompanied by her husband, the innovative vibraharpist and bandleader Red Norvo, and the members of the John Kirby Sextet, a dapper instrumental ensemble that frequently performed jazz versions of familiar classical pieces. (The Complete Columbia Recordings of Mildred Bailey, Mosaic MD10-204. This is a boxed set of Bailey’s recordings released last year by a mailorder firm specializing in historical reissues, and it can be ordered by calling 203-327-7111 or visiting

5. Chet Baker: “He Was Too Good to Me.” Music by Richard Rodgers, lyrics by Lorenz Hart.

Richard Rodgers collaborated with two different lyricists during his long reign as Broadway’s most successful tunesmith. Lorenz Hart, a dwarfish, self-hating homosexual, wrote astonishingly well-crafted lyrics in the W.S. Gilbert tradition, some sardonically amusing and others full of the anguish of unrequited love. Oscar Hammerstein II, a veteran who had previously collaborated with Jerome Kern on Show Boat, was more optimistic, sometimes to the point of naiveté. Rodgers and Hammerstein had bigger hits, but Rodgers and Hart usually wrote better songs—especially “He Was Too Good to Me,” an epitome of Hart’s dark view of love, set to one of Rodgers’s marvelously sweeping melodies (note especially the octave-spanning arpeggio that opens the bridge).

Like many standards, this one is designed so that it can be performed by a singer of either sex by changing the relevant pronouns. As “She Was Too Good to Me,” it was recorded in 1974 by Chet Baker, a celebrated cool-jazz trumpeter who frequently doubled as a vocalist. Baker used his thin, fragile voice with extreme sensitivity, and though he was barely a singer in the strict sense of the word, his ballad interpretations at their best have a rare poignancy. Also heard on this recording is a lyrical trumpet solo that leaves no doubt of Baker’s distinction as an instrumentalist (She Was Too Good to Me, CTI/CBS ZK 40804).

6. Tony Bennett: “I Walk a Little Faster.” Music by Cy Coleman, lyrics by Carolyn Leigh.

Cy Coleman and Carolyn Leigh were among the last traditional songwriters to win widespread recognition before the arrival of rock-and-roll. They are best known for such hard-swinging songs as “Witchcraft,” “I’ve Got Your Number,” and “The Best Is Yet to Come,” in which Coleman’s riffy, rhythmically insistent melodies (he started out as a jazz pianist) serve as an effective backdrop for Leigh’s droll, often sexually suggestive lyrics. But they also produced some of the most memorable standard ballads of the 1950’s and 60’s, among them the ruefully idealistic “I Walk a Little Faster,” whose chiseled melody opens with an unexpected leap of a ninth.

Tony Bennett, who introduced “I Walk a Little Faster,” is one of the few Italian-style tenors to sing American popular song idiomatically (though he rarely made full use of his upper register, generally preferring to stay in the high baritone range). A balladeer of utter sincerity, Bennett is also at ease with the rhythmic idiom of jazz, and has probably recorded with more distinguished jazz musicians than any other pop singer of his generation. After a period of temporary eclipse, he was rediscovered by younger listeners in the 80’s, and he continues to perform around the world as one of the last surviving icons of the great days of pre-rock popular singing (Who Can I Turn To, Columbia CK 66503).



To be continued

Except as indicated, all of these CD’s can be purchased online by viewing this article on COMMENTARY’s website:



1 American Popular Song: The Great Innovators 1900-1950 (Oxford, $40.00), written by the songwriter Alec Wilder in collaboration with Maher and originally published in 1972, remains the standard critical discussion of pre-rock American popular song. I have drawn extensively on this idiosyncratic but masterly work.

2 W.S. Gilbert, who wrote the words for the operettas of Sir Arthur Sullivan, was frequently cited by prewar songwriters as a major influence.


About the Author

Terry Teachout is COMMENTARY’s critic-at-large and the drama critic of the Wall Street JournalSatchmo at the Waldorf, his first play, runs through November 4 at Long Wharf Theatre in New Haven, Connecticut.

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