Ted Gioia has written a book called The Jazz Standards, which is an encyclopedic approach to the most popular jazz songs since it started in New Orleans at the turn of the previous century. Most of the articles are fairly short and readable though sometimes they can get quite technical, as in this from Gioia's article on “Stella by Starlight.”
"The structure is conventional in length, with the melody filling up the expected 32 bars. But everything else about it breaks the rules. Instead of the usual repeats found in American popular song, “Stella by Starlight” is a masterpiece of through-composed misdirection. At bar eight, where one would normally get a repeat of the A theme in most Tin Pan Alley songs, we do go to the tonic chord, but this is actually its first appearance in the piece. We might now expect that the repeat will come in bar 16, but here Young has another surprise in store—a gut-wrenching modulation, in which the melody is held on an altered note of the chord for a full bar. The final eight bars are as close as we will get to a recapitulation of the main theme, but even here Young tinkers with his melody and chords, only lingering on the familiar opening motif for two bars before heading off toward a different path to a final resolve.”*" You can find versions of the song by Miles Davis, Ella Fitzgerald, Frank Sinatra, Ray Charles, Anita O'Day, and The Bill Evans Trio on Youtube.
*Ted Gioia, The Jazz Standards: A Guide to the Repertoire, 400.
Not everything is as technical as the article on Stella. In the article on Hoagy Carmichael's greatest hit we learn, for example, that it should be “Star Dust,” not “Stardust.” We also learn the history of “The Lady is a Tramp” and that in one film in which it was featured, the 1948 biopic Words and Music, the white music director, Lennie Hayton, decided to feature his black wife, Lena Horne, singing the song. While inter-racial marriage is more common than it used to be, thanks to the Loving decision, it was pretty uncommon in the 1940s, and was definitely frowned upon. We also learn that Lena's segment was filmed in such a way that it could be excised when the film played in the South. The article on “Love for Sale,” which is a record I remember my father playing back in the '50s, discusses the bawdy nature of the song. I had always thought that “Take Five” was a Dave Brubeck composition, but Gioia says it was composed by Paul Desmond at Dave's suggestion. He comments on how the tune is sometimes performed very badly by groups just starting out. He also mentions, and I had not known this, that when Desmond died in 1977 his will provided that royalties from it go to the American Red Cross, which has received about $6,000,000 from it, and named a room in its D.C. headquarters after Desmond.
Much of the background on the songs is fascinating, and if you're over your head, as I am, when he discusses tonics and bars, unless we're talking alcohol, you can either read that material, or skim over it to the history and the recommended versions.
As I said, it's encyclopedic, so you can just flip around at any time, and find something interesting.
Next up, a David Weber book about treecats.