During the 1980s, she worked as a cabaret singer accompanying herself on piano, performing jazz, traditional pop, and standards from the Great American Songbook.

The song appeared on Streisand's album, Higher Ground, which debuted at the top of the Billboard 200 and gave Callaway her first platinum record.

Callaway's music and lyrics have also been recorded and performed by Karrin Allyson, Liz Callaway, Barbara Carroll, Blossom Dearie, Michael Feinstein, Harvey Fierstein, Carole King, Patti LuPone, Amanda McBroom, Donna McKechnie, Liza Minnelli, Peter Nero, and Lillias White.

In September 2005, Callaway performed her song "Let the Saints Come Marching" on a national TV broadcast on the Fox News Channel.

She recorded the song with Kenny Werner, the Siddha Yoga International Choir, and five-year-old Sonali Beaven, who sang in honor of her father who died on Flight 93.

She appeared in the movie The Good Shepherd and in Volare for Jim Henson Productions, directed by Tamela D'Amico.

Her voice has been heard in TV jingles and voice-overs, including spots for Coca-Cola, Ethan Allen, and State Farm.

She produced Singer's Spotlight with Ann Hampton Callaway featuring Liza Minnelli and Christine Ebersole.