Stern's solo debut, "Upside Downside", with Jaco Pastorius, David Sanborn, and Bob Berg, was released on Atlantic Records in 1986. From 1986 through 1988, he was a member of Michael Brecker's quintet, appearing on "Don't Try This at Home." His second Atlantic album, 1988's "Time in Place", featured Peter Erskine on drums, Jim Beard on keyboards, Jeff Andrews on bass, Don Alias on percussion and Don Grolnick on organ. His next album, "Jigsaw", was produced by guitarist Steve Khan and included the song "Chief", Stern's tribute to Miles Davis.