Sydney Pollack initially never considered Meryl Streep for the role of Karen Blixen as he figured she wasn't sexy enough. Streep landed the part by showing up for her meeting with the director wearing a low-cut blouse and a push-up bra.
Early in the film, Baroness Karen Blixen is introduced to her servants. Although the scene is inter-cut with close-ups and other inserts in the film, the first take was filmed as one long shot that required Streep to meet and exchange dialogue with several other characters. As soon as director Sydney Pollack yelled "Cut," Streep, wearing a high-collared shirt and snug jacket, yelled "get this thing off of me!" and ripped open her jacket. A beetle the size of Streep's hand had crawled down the front of the jacket moments after the camera rolled, yet she continued filming the scene, Much of it remains in the final film.
In one scene, Karen Blixen, travels across dangerous terrain to bring supply wagons to her husband's regiment. During the night, a lion attacks one of the oxen and Karen tries to fight it off with a whip. Meryl Streep was assured that the lion would be tethered by one of its back legs so he couldn't get too close. When the scene was shot, the lion had no restraint, and it got closer than Streep anticipated. The fear on her face is real.
Karen Blixen remains the only woman who has ever been invited to drink in the men's bar at the Muthaiga Country Club. Certain rules have been relaxed over the years, men are even allowed in certain parts of the club without jacket and tie, but the "men only" rule remains. Another bar allows women.
Robert Redford initially intended to play Denys Finch Hatton as an Englishman. Director Sydney Pollack felt it would be too distracting for audiences. Redford had to overdub some of his lines from early takes, when he used a trace of English accent.
Production designer Stephen B. Grimes spent a year building a replica of Karen Blixen's house and 1913 Nairobi. The film's sets were built not far from where Blixen had once lived, in a town now called Karen.
When Denys washes Karen's hair, he quotes from "The Rime of the Ancient Mariner" by Samuel Taylor Coleridge. One line, "He prayeth well, who loveth well both man and bird and beast," is inscribed on the real Denys Finch Hatton's gravestone.
While he was editing the picture, director Sydney Pollack used musical selections from John Barry to act as his temp track. When it came the time to actually score the film, Barry seemed like the perfect choice.
Felicity is modeled on Beryl Markham, another writer who lived in East Africa and was supposed to be another of Denys Finch Hatton lovers. Markham was also one of the first women to fly across the Atlantic. Sydney Pollack was fortunate enough to meet the elderly Markham early in pre-production.
The trivia items below may give away important plot points.
In real life, Karen and Denys' romance was slightly different. They met at a hunting club, not out on the plains. He disappeared for two years on military assignment in Egypt. He started flying and taking tourists on safaris after he moved in with Karen, not before. Karen learned of his death from some friends in Nairobi. The film never mentions that Karen miscarried their baby.
Nicolas Roeg planned to direct the film in the early 70s, using a screenplay written by Judith Rascoe. The scene where Bror informs Karen Blixen of Finch Hatton's death is a leftover from that treatment.
The man who giving the eulogy at Berkeley Cole's funeral is an actual preacher. Mike Harries, known as the Flying Preacher, is from an old, pioneer family that, among other things, brought sisal to Kenya. Mike had been hired to assist the English actor originally hired for the part. Bad weather that delayed filming, and the actor's fondness for food and drink paid for by Sydney Pollack, prompted Pollack to send him back to England and hire Mike for the small, but very important, role.