His father Jacobus Heesters (1865–1946) was a salesman and his mother Geertruida Jacoba van den Heuvel (1866–1951), a homemaker.

His signature role was Count Danilo Danilovich in Franz Lehár's Die Lustige Witwe (The Merry Widow).

During his time in Germany, he performed for Adolf Hitler and visited the Dachau concentration camp, which made him a controversial figure for many Dutch.

[3] Joseph Goebbels placed Heesters on the Gottbegnadeten list as an artist considered crucial to Nazi culture; he was the only non-German included.

[8][9] At the same time, Heesters was idolized by the Swingboy subculture, who admired his pale face and combed long black hair and tried to copy his attire.

[13][14] According to German writer Jürgen Trimborn however, the interview with Matejka may not be reliable as it occurred some 50 years after the performance was said to have taken place.

In its ruling, the German court did not find whether Kühn's allegations were true, but rather that too much time had passed for an accurate determination of fact to be made.

[citation needed] On 13 December 2008, at the age of 105, Heesters apologised for calling Adolf Hitler a "good chap" on the popular German TV show Wetten, dass..?.

[20] Heesters played smaller roles in his last years, as he began to lose his eyesight due to macular degeneration and could not perform on stage for long periods of times.

His younger daughter Nicole Heesters is a well-known actress in the German-speaking world, as is his granddaughter Saskia Fischer.

[26] He was fitted with a heart pacemaker and following a good recovery was allowed to go home less than a week later on 4th December 2011 just in time to spend his 108th birthday the next day with family.

He did not feel strong enough to make the planned stage appearance to sing in celebration of his birthday and also had missed the premiere of his last film, Ten.