Five Good Covers presents five cross-genre reinterpretations of an oft-covered song.

Many folk and blues songs derive from other songs, since so often they were originally transmitted by oral tradition and not sheet music or recordings. Performers would hear a song, and change it for artistic purposes, or because they misremembered what they heard, creating a big version of the game “Telephone.” So, when a song’s origins are unclear, how do you determine what is the “original” version, and what are “covers?” That’s the issue that we get when discussing “St. James Infirmary,” a song whose origin is shrouded in mystery. There’s even a book about its roots, a blog, and a number of essays, but there doesn’t appear to be any universally accepted conclusion.
Some believe that the song derives from a tune called “The Unfortunate Lad” or “The Unfortunate Rake,” about a man dying of a venereal disease. Although that theory appears to be losing favor, and that song may actually be more closely related to “Streets of Laredo,” a cowboy song. Another song, “Those Gambler’s Blues,” (or just “Gambler’s Blues”), may be the source material, because, like the more modern versions of “St. James Infirmary,” it initially focuses not on the narrator, but on his sweetheart, who is dead in the hospital. (And some posit other source material.) The first sheet music for “Gambler’s Blues” was published in 1925 by Carl Moore and Phil Baxter, and the poet Carl Sandburg published a book, The American Songbag, in 1927 with two different versions of “Gambler’s Blues.” The same year, Fess Williams and his Royal Flush Orchestra released the first recording of the song.
In 1928, Louis Armstrong and his Savoy Ballroom Five recorded a version of the song, as “St. James’ Infirmary,” erroneously crediting the song to Don Redman, a musician who had arranged the song for Armstrong, and had briefly joined his band. Subsequent releases of the song, however, credited “Joe Primrose” as the writer, which was a pseudonym for music publisher Irving Mills. This version, a slow blues in a minor key, is also the version of the song that seems to be the most influential to later covers, so, for the purposes of this post, we will consider this version the “original.”
However, due to the song’s uncertain lineage, over the years performers have taken liberties with the lyrics, adding, subtracting and moving around sections as they see fit.
Cab Calloway — St. James Infirmary
In 1931, Cab Calloway released a version of the song that was more theatrical and uptempo than the Armstrong version. It charted at no. 3, not quite as high as his more famous song, “Minnie the Moocher,” which topped the charts that year. Calloway was a huge star in the pre-WWII era, as a musician and in films. He was the first Black American both to sell a million copies of a record and to have a nationally syndicated radio show. He remained popular for decades, mostly on the coattails of “Minnie the Moocher,” which he introduced to new audiences in 1980’s The Blues Brothers. But back in 1933, Calloway contributed a version of “St. James Infirmary” to a Betty Boop cartoon, Snow White, in which he sings, and his dancing was rotoscoped into the film, including what is definitely a proto-moonwalk, decades before Michael Jackson was born.
Josh White — St. James Infirmary
Josh White was a folk and blues musician who appeared in films and on stage, was a civil rights activist who was blacklisted during the McCarthy Era and had a career that lasted from the 1920s to the late 1960s, ending not long before his death in 1969. His talent, good looks, and charm allowed him to crossover from his early days releasing “race” records to popularity with white audiences. He even forged a friendship with President Franklin Roosevelt and First Lady Eleanor, who were the godparents to his son, Josh White, Jr., also a musician (who died earlier this year). For whatever reason, White’s memory seems to have faded a little in comparison to some of his contemporaries. White’s version of the song is a folky blues, with original lyrics, and is very different from the more jazz-based approaches of Armstrong or Calloway.
Sly and the Family Stone — St. James Infirmary
We recently lost Sly Stone, a man whose genius continued to be acknowledged long after he stopped making chart-topping hits. Part of his brilliance was acknowledging and incorporating diverse musical and social influences into his music, which is why his multi-racial, mixed gender band was fluent in rock, jazz, soul, R&B, pop, funk and probably other genres that I’m not thinking of. So, if you went to the Fillmore East on October 4, 1968—for the early show—in addition to some of their already recorded songs, and some works in progress, you would have been treated to a relaxed, jazzy, funky, instrumental version of “St. James Infirmary” that featured the trumpet playing of band member Cynthia Robinson, one of the first female trumpeters in a major American rock band. It does not appear that they ever played it again.
Lily Tomlin with Howard Shore and His All-Nurse Band — St. James Infirmary
After all the hoopla about Saturday Night Live’s 50th season, it might be hard to remember that SNL was not always a venerable mainstay of late-night television, and that it did not always follow the current formulaic format. I’m old enough to remember watching the first episode back in 1975, and much, if not all, of the first season, when shows often had more than one musical guest (and sometimes none), and when many of the musical guests (and hosts) were not big stars (and the show wasn’t even called SNL). Episode 6, which aired on November 22, 1975, was hosted by Lily Tomlin, best known as a comedian who had starred on Rowan and Martin’s Laugh-In and who had released a number of hit comedy records. In 1975, she showed a different side of her talents, with a dramatic role in Robert Altman’s Nashville, for which she was nominated for an Academy Award and a Golden Globe. But on SNL, she also showcased her singing ability, as the only musical guest. She sang a sultry, jazzy version of “St. James Infirmary,” supported by the show’s band, billed as Howard Shore and His All-Nurse Band (all in appropriate costume). That’s Paul Shaffer on piano. Her version starts with lyrics that appear to have been added by Lou Rawls in his cover.
Silkroad Ensemble featuring Rhiannon Giddens — St. James Infirmary Blues
Speaking of multi-talented women, I give you Rhiannon Giddens. Multi-instrumentalist, classically trained singer, songwriter, musicologist, music historian, festival organizer, actress, TV host, and activist, she’s written operas, ballets, and songs in many popular (and less-popular) genres. And she’s a MacArthur Fellow, to boot. I’m a big fan, if you haven’t guessed. In 2016, she sang “St. James Infirmary,” as a guest vocalist with The Silkroad Ensemble, a multi-cultural collective of brilliant musicians and other artists who perform in various configurations, creating amazing cross-cultural music on their album Sing Me Home. If you just listen to Giddens’ vocals in isolation, you’d hear a jazz-blues take that owes a lot to Cab Calloway. But the music is very different. Starting with Artistic Director Yo-Yo Ma’s classically based cello, which is joined by accordion (not a combo that you often hear in classical music), it ultimately includes elements of klezmer, New Orleans jazz, South American music, and, oh, yeah, a Japanese flute and a Chinese yanquin (like a hammered dulcimer). Which sounds like it could be a mess, but in these musicians’ hands (and mouths), is remarkable. (Giddens had previously covered it with Tom Jones on Jools Holland’s BBC TV show in late 2015, in a more conventional arrangement).
Yo-Yo Ma, who occasionally ventured into other genres beyond classical, retired as Artistic Director in 2017, and Giddens succeeded him in 2020. I saw her perform the song with Silkroad live in 2022, and it was incredible.




Hugh Laurie’s version is also quite good: https://www.youtube.com/watch?v=AzEBH6DZJVk