Though Robertson had been a professional musician since the late 1950s, notably a founder of and primary songwriter for The Band, this was his first solo album.

The album includes contributions from Rick Danko and Garth Hudson of The Band, as well as U2 and Peter Gabriel, both of whom had worked with Lanois.

U2's contributions are heard in the song "Sweet Fire of Love", a duet of sorts between Robertson and U2 lead singer Bono, and in "Testimony" again featuring backing by U2.

[2] Film producer Art Linson encouraged Robertson to focus on creating a solo record when the two vacationed together in Rome that same year.

[3] Robertson then began conceptualizing the idea, starting with creating a setting called "The Shadowland" where the songs in the album would take place.

Robertson also brought in The BoDeans to provide group vocals for some of the tracks on the album, most notably on "Showdown at Big Sky".

Robertson and U2 lead singer Bono then improvised a set of lyrics in the studio while the band's instrumentalists played behind them, creating a 22-minute track that was edited into the song "Sweet Fire of Love".

Robertson attributed the direction he was taking to the recent passing of fellow Band alumnus Richard Manuel, who had committed suicide in a hotel room in Florida in March 1986,[8] and dedicated the song to him.

At Bearsville Studios, Robertson worked on a version of "What About Now" that was withheld from the final release of the album, as well the track "American Roulette," which was inspired by a screenplay he had written.

[19] The album did receive negative criticism as well, with Greil Marcus later deriding it as "draped in curtains of overproduction" with "themes so elaborated and vocals so disguised it was hard to discern an actual human being behind any of it.

"[20] Robert Christgau wrote that it "took some guts for such an unrepentant Americana-monger [like Robertson] to risk Anglophobe wrath" by collaborating with Gabriel and Bono, but he was very disappointed with the results and graded the album with a C+.

[21] Barney Hoskyns dismissed it as sounding "bloated and grandiose," with Robertson "overreaching himself and getting lost in flights of airy verbosity.

"[22] Elvis Costello, a lifelong fan of The Band, said he "didn't like it at all," and that "it was like [Robertson] decided to make a Peter Gabriel album, whereas his songwriting was much more interesting and enigmatic when he was working on that smaller scale.

When asked about the inspiration for the album's single "Somewhere Down the Crazy River", Lanois commented, "Robbie Robertson was describing what it was like to hang out in Arkansas with Levon Helm in his old neighbourhood.

"[30] This song is notable as Robertson's only solo hit in the United Kingdom, reaching number 15 on the UK Singles Chart.

Because of the popularity of the BoDeans in their home state of Wisconsin, "Showdown at Big Sky" received significant airplay on Milwaukee AOR radio.