linguistic:paraphrasing
1988–1993: Chalk Mark in a Rain Storm and Night Ride Home

Mitchell continued experimenting with synthesizers, drum machines and sequencers for the recordings of her next album, 1988's Chalk Mark in a Rain Storm. She also collaborated with artists including Willie Nelson, Billy Idol, Wendy & Lisa, Tom Petty, Don Henley, Peter Gabriel, and Benjamin Orr of the Cars. The album's first official single, " My Secret Place ", was a duet with Gabriel, and reached the top 50 on the Canadian singles chart. The song "Lakota" was one of many songs on the album to take on larger political themes, in this case the Wounded Knee incident, the deadly battle between Native American activists and the FBI on Pine Ridge Indian Reservation in the previous decade. Musically, several songs fit into the trend of world music popularized by Gabriel during the era. Reviews were mostly favorable towards the album, and the cameos by well-known musicians brought it considerable attention. Chalk Mark ultimately improved on the chart performance of Dog Eat Dog, peaking at No. 45.

In 1990, Mitchell, who by then rarely performed live, participated in Roger Waters ' The Wall Concert in Berlin. She performed the song " Goodbye Blue Sky " and was also one of the performers on the concert's final song " The Tide Is Turning " along with Waters, Cyndi Lauper, Bryan Adams, Van Morrison and Paul Carrack.

Throughout the first half of 1990, Mitchell recorded songs that appeared on her next album. She delivered the final mixes for the new album to Geffen just before Christmas, after trying nearly a hundred different sequences for the songs. The album Night Ride Home was released in March 1991. In the United States, it premiered on Billboard ' s Top Albums chart at No. 68, moving up to No. 48 in its second week, and peaking at No. 41 in its sixth week. In the United Kingdom, the album premiered at No. 25 on the albums chart. Critically, it was better received than her 1980s work. This album was also Mitchell's first since Geffen Records was sold to MCA Inc., meaning that Night Ride Home was her first album not to be initially distributed by WEA (now Warner Music Group).