Freedom to Love (Freiheit für die Liebe) 54 years old

It is a sex education film of sorts dedicated to all forms of human sexuality.

Credits

Name	Character
Hugh Hefner He was 43, 91 years old when he died	as Himself
Paula Shaw She was 28, now 82 years old	as Sandy
John Bowen He was 171, 72 years old when he died	as Himself
Daniel D. Halleck He was 23, now 78 years old	as Hank
Sacha Kraamwinkel	as Brigitte
Kenneth Tynan He was 42, 53 years old when he died	as Himself
Richard Bright He was 32, 68 years old when he died	as Billy the Kid
Monique Kraamwinkel	as Christine
Billie Dixon	as Jean Harlow
Marie Antoinette She was 213, 37 years old when she died	as Deborah

Name	Department
Reginald Puhl as Producer. He was 38 (85) years old when He died	Production