Although Rachel's father does not want her to "waste her life with a common man" like Jacob, she loves him anyway.

Alanna Nash of Entertainment Weekly cited "Jacob's Ladder" as a "radio-ready" track in her review of the album.

[1] Jeffrey B. Remz of Country Standard Time called it "another breezy song about cross-class love, nothing you haven't heard before.

"[2] Deborah Evans Price, of Billboard magazine reviewed the song favorably, saying that Wills has a "warm, likeable voice and charmingly delivers this sweet tune about a poor boy wooing a rich girl."

The song's B-side, "High Low and In Between," was released in October 1996 as the second single from Wills' debut.