Hitler and Hoffmann became close friends. Historian Alan Bullock succinctly described Hoffmann as an "earthy Bavarian with a weakness for drinking parties and hearty jokes", who "enjoyed the licence of a court jester" with Hitler. Hoffmann was part of the small party which drove to Landsberg Prison to meet Hitler when he was released from prison on parole on 20 December 1924, and he took Hitler's picture. Later, Hoffmann often dined with Hitler at the "Berghof" or at the Führer's favorite restaurant in Munich, the Osteria Bavaria, gossiping with him and sharing stories about the painters from Schwabing that Hoffmann knew. He accompanied Hitler on his unprecedented election campaign by air during the presidential election against Field Marshal Paul von Hindenburg in 1932.