Al Jolson was probably the single most acclaimed musical-theater singer of his generation at the time, but his work has come under a shadow of disrepute because he performed most of his roles in blackface. But it has to be remembered that blackface didn’t always have the implications back then that it invariably has now (it’s worth remembering that even actual Black performers like Bert Williams indulged in it fairly frequently). Although some blackface performance engaged in mean-spirited caricature that even then was questionable at best, apart from perhaps a few of his late-career movie roles (like the “Goin’ to Heaven on a Mule” number in Wonder Bar), Jolson tended to use the paint more as the equivalent of a Commedia dell’arte mask than an attempt at racial caricature (and let’s remember that the Harlequin mask in the Commedia dell’Arte had some racist implications itself in the beginning). I understand why Jolson’s performing persona wouldn’t be considered remotely acceptable today, but the fact remains that he was a marvelous singer and one of the greatest showbiz personalities of his era, and his work still holds up today. And one of the strongest indicators of his lack of genuine racism is his extreme fondness for the songs of Stephen Foster…indeed, the last thing Jolson ever recorded was an album of Foster songs. And Foster, while he often wrote songs for the Minstrel Shows of the 1800s, was actually an exceptionally progressive thinker for the period, and he used his compositions to subvert the ugly caricature of the Minstrel Show by writing dignified and touching songs for Black characters. This particular song, if you can get past the title that no-one would use today, is a perfect example, a moving and human depiction of a man facing death with dignity set to one of Foster’s greatest melodies. And if Jolson’s performance of it is, like most of his work, a trifle overacted, there’s still certainly nothing of caricature or even disrespect in it, and if you played it for a listener who had never seen an image of Jolson performing, I highly doubt they would find anything to reproach about it.
Verdict: I understand why people are bothered by Jolson’s performing style, but if you ignore historical context altogether, almost every great artist of the past would seem offensive. And in any case, great music is great music.