I first heard “Ace in the Hole” on Dave Van Ronk’s 1963 album with the Red Onion Jazz Band, In the Tradition. It was written around 1909 by a couple of obscure songwriters, James Dempsey and George Mitchell, and is a musical evocation of the New York borderline underworld limned by Damon Runyon in the stories that inspired Guys and Dolls. Dave was a devotee of this kind of New Yorkiana — his rock band, the Hudson Dusters, was named for a notorious street gang of the 1800s — so he naturally jumped on it.

I’m pretty sure Dave picked it up from Lu Watters’s Yerba Buena Jazz Band, a San Francisco group that was one of the first and best white trad revival bands, who recorded it in the 1940s with the New Orleans trumpeter Bunk Johnson — Watters’s outfit is not well remembered these days, but Dave was a dedicated “moldy fig” traditionalist in his teens, devoted to Bunk’s work, and developed an appreciation for the San Francisco bands during a shore visit in his brief period as a merchant seaman.

I’d heard Dave’s version and knew that provenance, but thought of it as an obscurity until I did some research for this post and found it was recorded by over a hundred groups and artists, starting with a bunch of minor white jazz bands in the 1920s, including one in Berlin, then various western and hillbilly swing bands, then Frankie Laine, Connie Francis, Bobby Darin and Johnny Mercer, Judy Henske, and a lot of others, including a bizarre version from 1969 by the honky-tonk singer Hank Thompson, rewritten as a critique of hippies, protesters, and other good folks of that time, which could easily be revived by the Trump crowd today. (I’m not linking it, but it’s available online if you want to check it out.)

Dave’s original recording only had the one verse and one and a half choruses, with the rest of the space taken up by solos from the band, and he never played it solo until near the end of his life. Then he worked up a really nice guitar chart, wrote a second verse, and filled out the second chorus — as I’ve noted in my posts for “That’ll Never Happen No More” and “Somebody Else, Not Me,” he regularly wrote additional lyrics for songs he thought needed some help. I never learned his new verse, but use his extra lyric for the second chorus, though I’ve changed one line that didn’t seem to fit the theme, staying true to his memory by using the term clydes, meaning “squares,” which I learned from him.

Speaking of archaic hipster argot: a Missouri bankroll was a roll of one dollar bills (or sometimes paper cut to the same size) with a couple of high-denomination bills on the outside, flashed to create the illusion that the bearer was loaded. Tenderloin was a common term in the late 19th and early 20th century for prostitution districts, extrapolated from the original Tenderloin, the Manhattan prostitution district running from about 14th to 42th Streets between 6th and 8th Avenues, so named (according to a popular legend) when a new police captain was assigned to that district, which like all such districts was famous for bribery, and commented that he’d been eating chuck steak all his life and was looking forward to some tenderloin.

I started playing this when Sandrine and I were living in New Orleans in the early 2000s, staying with David and Roselyn, and jamming with them and whoever else dropped by in the evenings. They had a fake book with this in it, and no one else knew it until one night a trumpet player showed up who was from the Bay Area, so we played it and I’ve been messing with it ever since.