Guenter de Bruyn has arguably become the most successful former East German author since the Wende. The present study traces his career from his earliest literary publications in the 1960s, paying close attention to the impact cultural attitudes in the GDR at that time have subsequently had on the development of his writing. In addition to an examination of his creative work, de Bruyn’s extensive research into Germany’s cultural heritage, as exemplified by his acclaimed biography of Jean Paul, is also considered, revealing the fullness of his contribution as both author and literary historian.