The Traditional Ballad Index doesn't shed light on any really old versions of the song (earliest is 1927, from Sandburg's American Songbag, but I think the entry is worth posting:

Jerry, Go and Ile that Car [Laws H30]

DESCRIPTION: Larry Sullivan has spent forty years maintaining the railroads; he is proud of the state of the tracks and of never having had a wreck. As he lies dying, he asks to be buried by the tracks. His last words are, "Jerry, go and ile that car."
AUTHOR: unknown
EARLIEST DATE: 1927 (Sandburg)
KEYWORDS: train death work
FOUND IN: US(So,SW)
REFERENCES (6 citations):
Laws H30, "Jerry, Go and Ile that Car"
Belden, pp. 445-446, "The Old Section Boss" (1 text, very defective)
Sandburg, pp. 360-361, "Jerry, Go an' Ile That Car" (1 text, 1 tune)
Lomax-FSNA 216, "Jerry, Go and Ile that Car" (1 text, 1 tune)
Botkin-RailFolklr, p. 441, "Jerry, Go and Ile That Car" (1 text, 1 tune)
DT 691, JERRYILE
Roud #2192
RECORDINGS:
Warde H. Ford, "Jerry, will you ile that car" [fragment] (AFS 4215 B2, 1939; on LC61, in AMMEM/Cowell)
Harry "Mac" McClintock, "Jerry, Go Ile That Car" (Victor 21521, 1928; on RRinFS)
Art Thieme, "Jerry, Go & Oil That Car" (on Thieme06)
File: LH30

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The Ballad Index Copyright 2005 by Robert B. Waltz and David G. Engle.