Born to a Batak family in Medan, North Sumatra, Tobing moved to Jakarta in 1950 and began working in the entertainment industry.

[4] In 1942, following the Japanese occupation of the Dutch East Indies, his father came for him and brought Gordon to Plaju, Palembang, to work at the oil company.

With his uncle, Remus, and brother Douglas, Gordon established the band Rimba Boys, which played Hawaiian-style music.

[3] When the studio was producing its film Rakjat Memilih (The People Choose), Tobing was asked to find some singers to provide a soundtrack.

Tobing began boarding at the Hutabarat house in 1951, though he was told to leave in 1954 after beginning to woo the youngest daughter, Theresia.

The dancer Irawati Durban Ardjo recalled that this helped both the envoys and local organizing committees develop a sense of intimacy and familiarity.

The couple chose to elope and, on 15 August 1955, Gordon took Theresia from her home with the help of Douglas and a friend named Wim.

As Douglas left a false trail leading to Bogor to misdirect Theresia's parents, Gordon took her to Medan via Merak.

However, Tobing grew disappointed with the city, and in 1959 he and Theresia left Medan to return to Jakarta,[9] where they joined a group of non-government Indonesian artists and performers on a tour of Eastern Europe.

[2] In 1960, Tobing and his wife established the Impola vocal group; they worked with Koes Hendratmo [id] for a while, and often performed for state guests.

It describes him as surprising audiences by refusing to use a microphone and by walking off the stage and into the watching crowds, carrying his guitar and singing seemingly without any difficulty.

[2] Tobing would often take the bus rather than take a car,[12] and, when asked to perform at the Krems ad Donau music festival in Austria in September 1981, he had to seek a sponsor as he was unable to afford the ticket.