In 1982, several years after his initial invitation from Sonny Rollins, Broom would rejoin him to work with the jazz legend for five years of touring and the recordings No Problem and Reel Life. In 1987, Broom worked with Kenny Burrell in his Jazz Guitar Band and recorded Generation live at the Village Vanguard for Blue Note Records. That same year he was also invited to join Miles Davis' band, which lasted for a handful of performances. Broom relocated to Chicago in 1984, where he would eventually form his own trio and co-lead the Deep Blue Organ Trio (with Chris Foreman and Greg Rockingham). It was also where he would come full circle in meeting and working with Charles Earland, another newly transplanted Chicago resident. Together they recorded Front Burner and Third Degree Burn. Just before his untimely death in 1999, Earland had planned to form a trio with Broom and drummer Rockingham. During the '90s Broom collaborated with Dr. John, touring and making recordings, including Duke Elegant, which he co-produced.

Over the years Broom also became active in jazz education, beginning in 1982 when he taught for Jackie McLean's jazz program at the University of Hartford. He completed graduate work in jazz pedagogy at Northwestern University in 2005, and teaches at DePaul University. Also in 2005, after 20 years, Broom resumed work with his old boss and mentor Sonny Rollins. Bobby Broom's notable recordings include No Hype Blues (1995), Waitin' and Waitin' (1997), Modern Man and Stand! (both 2001), and the Deep Blue Organ Trio's Deep Blue Bruise and Goin' to Town.