In 1991, she wrote her third children's book, The Fisherman's Song, which was based on the song of the same name from her 1990 album Have You Seen Me Lately. That same year, Simon performed a duet with Plácido Domingo on the song "The Last Night of the World" (from the stage musical Miss Saigon) on Domingo's album The Broadway I Love. In 1992, Simon wrote the music for the Nora Ephron film This Is My Life, and the soundtrack album was released shortly thereafter. It includes the song "Love of My Life", a No. 16 Adult Contemporary hit. In 1993, she contributed her performance of "In the Wee Small Hours of the Morning", from her 1990 album My Romance, to the Nora Ephron film Sleepless in Seattle. It was also included on the film's soundtrack album. Simon recorded the same song in combination with "Guess I'll Hang My Tears Out to Dry" with Frank Sinatra for his album Duets (1993). By this point, Sinatra's health was too poor for him to record, so the feat was accomplished by producers lifting an isolated prerecorded vocal track from an earlier performance and laying a new background – and Simon – behind it. The album later earned a nomination for Best Traditional Pop Vocal Performance at the 37th Annual Grammy Awards.
in 1991 she wrote her third children's book the fisherman's song which was based on the song of the same name from her 1990 album have you seen me lately that same year simon performed a duet with plácido domingo on the song "the last night of the world" (from the stage musical miss saigon) on domingo's album the broadway i love in 1992 simon wrote the music for the nora ephron film this is my life and the soundtrack album was released shortly thereafter it includes the song "love of my life" a no 16 adult contemporary hit in 1993 she contributed her performance of "in the wee small hours of the morning" from her 1990 album my romance to the nora ephron film sleepless in seattle it was also included on the film's soundtrack album simon recorded the same song in combination with "guess i'll hang my tears out to dry" with frank sinatra for his album duets (1993) by this point sinatra's health was too poor for him to record so the feat was accomplished by producers lifting an isolated prerecorded vocal track from an earlier performance and laying a new background – and simon – behind it the album later earned a nomination for best traditional pop vocal performance at the 37th annual grammy awards