During his time with the band, Tilahun came into conflict with the Ethiopian government after a attempted coup d'état in December 1960 by the Imperial Bodyguard. He was arrested and put in prison for some time. Tilahun moved to the National Theater where his success continued. His tenor singing was regarded as the best Ethiopian pop voice of the 1960s. His popularity was such that he appeared three times in front of Emperor Haile Selassie I. During a visit, the Emperor advised him not to abuse his talent. Recordings made by Tilahun during the 1970s and 1980s helped raise large sums of money to aid famine victims. The majority of his recordings were in Amharic, but he did also record a few in Oromo. In 1975, Tilahun released eponymous LP Tilahun Gessesse, Amha Records served as the label. With Ethio Grooves, Tilahun released Tilahun Gessesse Vol. The third version was released in the same year. When collaborating with The Walias, they together worked to re-recording the older version of LPs since 1983 under Misrach Music Group. Tilahun released his debut single "Yehagere Shita" in 1970, accompanied with 7", mono formats and Philp Philips served as the record label.
With these formats, Tilahun continued to release singles and EPs, including "Tiz Alegn Yetintu" (1970), with Mulatu Astatke, "Kulun Manqualesh", "Min Libejegn" (1972), "Aykedashm Lebe" (1974), and "Yikir Yibelatchew / Leyito Blaskerew" (1974).
He received an Honorary Doctorate Degree from Addis Ababa University, in appreciation of his contribution to Ethiopian music. He also received an award for his lifetime achievements from the Ethiopian Fine Art and Mass Media Prize Trust. Tilahun died on 19 April 2009 in Addis Ababa as he was being taken to hospital by his wife. He had just returned to Ethiopia from the United States. He had been in poor health for several years due to diabetes.
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