The Aviator

I know, it's not an older film. But the plot is! Howard Hughes was a producer, director, aviator beginning in the 1920s. The film stars Leonardo DiCaprio as Hughes with Gwen Stefani as Jean Harlow, Cate Blanchett as Kate Hepburn and Kate Beckinsale as Ava Gardner.

http://www.jonathanrosenbaum.com/?m=200412

The film begins with the shooting of "Hell's Angels". Production took about four years ending in 1930. Hughes completed the first film in 1928 but with the coming of sound, it was reshot for an additional $1.8 million! The finished product featured Jean Harlow, who was not in the 1928 production; it launched her career.

http://www.2blowhards.com/archives/2009/08/jean_harlow_was.html

Rosalind Russell also was given her start by Howard Hughes in "The Outlaw". She went on to star in such films as "His Girl Friday" and "Picnic".

http://www.hayinart.com/2004_03.html

One of the important aspects of the film is Hughes downward spiral as time goes on. He battled germ phobia and OCD all of his life and it finally began to take its toll in the 1940s when he began to disappear from public life.

http://panachereport.com/channels/more%20short%20stories/howardhuges.htm

Despite his ailments, Hughes always pressed on with his work. In 1946 he crashed his plane into a Beverly Hills neighborhood, suffering from a crushed collar bone, cracked ribs, crushed chest with a collapsed left lung, his heart shifted to the right side of his chest, and many third-degree burns.

http://www.pbs.org/opb

All the characters in the film made wonderful movies over the years, be sure to IMDB them and find some you like!