Rough Harvest is a collection of alternate, acoustic arrangements of John Mellencamp's favorite tracks, as well as several covers. Recorded mostly in 1997 (with the exception of "Under the Boardwalk," which was recorded in 1986, and "Wild Night" in 1994), the album fulfilled Mellencamp's contractual obligation with Mercury Records.
"It was very easy for me," Mellencamp told the St. Louis Post-Dispatch's Kevin C. Johnson of the acoustic arrangements on Rough Harvest in a September 30, 1999 article. "Actually, every song I ever wrote I wrote on acoustic guitar first. That's pretty much how the songs sound before I put electricity to them. When I start arranging, it's a big step when you have to add a band to the song."
On his cover of "Under the Boardwalk," which was originally the B-side of his 1986 hit "R.O.C.K. in the U.S.A." and was performed live on the Scarecrow Tour and The Lonesome Jubilee Tour, Mellencamp told the Post-Dispatch: "God bless the Drifters, but I thought the song was a little slow. I think that suited the times very well. I was a kid at the time, and that groove was a very urban groove, a very black groove, and what I did was take that groove and record it with a rock groove."