He was known for his songs such as "Lidah Tak Bertulang", "Tiada Maaf Bagimu", "Tinggi Gunung Seribu Janji", and "Widuri".

He then recorded popular songs like "Tiada Maaf Bagimu" and "Tinggi Gunung Seribu Janji" with the famous Pattie Sisters.

After performing in neighboring countries like Malaysia and Singapore, Bob moved to the United States in 1969 at the invitation of the Los Angeles-based Indonesian group Venturas to record some music.

He appeared in several Indonesian films, such as Gli Innamorati Della Becak (1958), Penasaran (1977), and Sebelah Mata (2008).

[5] Bob Tutupoly died of complications from a stroke on 5 July 2022 at Mayapada Hospital in South Jakarta.