The Jack O' Diamonds is a hard (unlucky) card to hold. Big Joe Williams uses that expression in his Baby Please Don't Go.
Riley Puckett & Clayton McMichen [as A Corn Licker Still In Georgia]
Jules Verne Allen [real Texan cowboy]
Tex Ritter [as Rye Whiskey in film Song Of The Gringo]
Mance Lipscomb [as Jack O' Diamonds Is A Hard Card To Play]
Big Brother & The Holding Company [in Coo Coo]
Walkers [as Jack O' Diamond, hit NL]
Blue Mountain [as Rye Whiskey]
Waylon Jennings [posthumous; recorded in the mid 90s]
Dave Matthews Band [as Rye Whiskey]
Gambler's song with deep English roots. Related to folk standard The Cuckoo and Irish ballad Bunclody. Also became an American fiddle warhorse as Drunken Hiccups, related to The Wagoner's Lad. Not to be confused, neither with Sippie Wallace's song for OKeh in '26 (with Louis Armstong) nor with Ben Carruthers' Jack O' Diamonds (see there). Ruth Brown's Jack-o-Diamonds ('54) was a Leiber/Stoller composition fist released by Jacki Fontaine (Forecast - '54).