Hildebrandt was born in Bunzlau, Lower Silesia, Weimar Germany (now Boleslawiec, Poland) where he attended school.

In World War II he became a Flakhelfer of the Luftwaffe but after four months was conscripted to the German Wehrmacht, in the same role.

In June 2007, a year after the Günter Grass Waffen-SS revelations, documents were released which showed that some prominent German intellectuals like Siegfried Lenz, Martin Walser and Dieter Hildebrandt had been members of the Nazi Party.

After finishing his studies Hildebrandt worked with Sammy Drechsel to found and develop the Münchner Lach- und Schießgesellschaft, a successful kabarett where he worked alongside cabaret artists such as Klaus Havenstein and Bruno Jonas.

From 1973 until 1979 Hildebrandt was the presenter and author of the cabaret show "Notizen aus der Provinz" (Notes From The Province), which was broadcast by ZDF.