Green’s Dictionary of Slang

(US black) serious, with no leniency.

1926		E. Richard ‘Whip It to a Jelly’ 🎵 Just like Anne, long and slim, when she whip it it’s too bad Jim / Lord she whip it to a jelly, and stir it in a bowl / Now you whip it to a jelly if you like good jelly roll .
1929		‘Barbecue Bob’ ‘It’s Just Too Bad’ 🎵 Tell me pretty mama why you fool around with him, / I cant tell you papa, it will be too bad Jim.
1930		Blake & Razaf ‘My Handy Man Ain’t Handy No More’ 🎵 The way he used to handle things was too bad Jim / That man was so efficient, full of pep and vim.
1941		Y. Rachell ‘Peach Tree Blues’ lyrics] I’m gonna get my step-ladder, I’m gonna climb up on your top limb; / If I get among your yaller peaches, you know It’s gon’ be too bad, Jim.
1954		(con. 1920s–30s) J.O. Killens Youngblood (1956) 422: Next time you here I ain’t gonna let you off so easy. It’s gon be too-bad-Jim.
1997		R.L. Burnside [song title] Too Bad Jim.