Classic Movies of Legendary Couple, Errol Flynn and Olivia de Havilland

Today, let’s talk Classic Movies of Legendary Couple-Errol Flynn and Olivia de Havilland! We previously talked about their performances apart, but today’s post is all about their wonderful movies together. Whether in swashbuckler, Western, or modern setting, Flynn and de Havilland are indeed one of the best-loved of all screen couples and their films are always enjoyable entertainment. The eight screen classics this dynamic duo made together, usually under the capable direction of Michael Curtiz, are as follows:

Captain Blood (1935) was their first romantic pairing. It is a fabulous sea-faring swashbuckler that includes an exciting seaside swordfight between Errol Flynn and Basil Rathbone (not the last time these two amazing swordsmen would meet on film). Flynn and de Havilland are youthfully enchanting and their on-screen chemistry is clearly apparent throughout the movie.

The Charge of the Light Brigade (1936), loosely based upon the classic poem by Alfred, Lord Tennyson, depicts the disastrous British Cavalry charge against Russian forces during the Battle of Balaclava in the Crimean War in 1854. Errol Flynn and Patric Knowles portray soldier brothers in love with the same girl (de Havilland) in this story that culminates with the infamous cavalry charge also known as “the magnificent blunder”. Don’t expect historical accuracy in this film, but do expect rousing adventure, romance, and a surprising outcome for our dynamic duo.

The Adventures of Robin Hood (1938) is our favorite of all the Flynn-de Havilland pairings and is the classic in the spotlight today. With a supporting cast that includes the considerable talents of Claude Rains, Basil Rathbone, Alan Hale, Patric Knowles, Eugene Pallette, Una O’Connor, and Ian Hunter, this tale of Robin Hood and the “merry men” of Sherwood Forest is, in our opinion, the most enjoyable of all “Robin Hood” films to date. There is just something about the brilliance of Technicolor, the magnificent musical score by Erich Wolfgang Korngold, and the presence of dashing Errol Flynn as Robin Hood and beautiful Olivia de Havilland as Maid Marian that cannot be recaptured by today’s versions. Robin’s exchanges with Little John (Hale), Friar Tuck (Pallette), and Prince John (Rains) are amusing, often sarcastic, and great fun to watch. The archery competition is exciting and the climactic swordfight between Robin and Sir Guy (Rathbone), as they descend a spiraling stairway, is spectacular. Errol Flynn and Olivia de Havilland absolutely light up the screen as their characters fall in love, despite a somewhat dubious beginning. We adore The Adventures of Robin Hood and recommend it highly to anyone who enjoys action-packed drama mixed with romance and humor.

Four’s A Crowd (1938), co-starring Rosalind Russell and Patric Knowles, is a screwball romantic-comedy that we have never had the pleasure of seeing, but we do hope to remedy that soon. After watching several clips of this film, we think it looks very entertaining and a delightful change-of-pace for Flynn and de Havilland. We intend to check on the availability of this film with Netflix or Blockbuster (see our banner ads on this blog for classic movie rentals or purchases).

The Private Lives of Elizabeth and Essex (1939) stars Bette Davis as Queen Elizabeth, Errol Flynn as the Earl of Essex, and Olivia de Havilland as Lady Penelope Gray. This opulent costume drama is beautifully filmed in Technicolor and tells the tale of the middle-aged Queen and her love for the younger, dashing and very ambitious Essex. Lady Penelope Gray is also in love with Essex, but his heart belongs to Elizabeth. The story’s plot is one of complicated intrigue that results in heartbreaking decision-making by Queen Elizabeth who must put her love of country before her love for Essex. The talented supporting cast includes Vincent Price, Alan Hale, Donald Crisp, Judith Anderson, and young Nanette Fabray.

Dodge City (1939) pairs Flynn and de Havilland in a Western for the first time. Alan Hale and Guinn “Big Boy” Williams are Flynn’s humorous sidekicks in this film that has hero, Wade Hatton (Flynn), cleaning up the “wild and woolly” town of Dodge City, Kansas. As he attempts to make the town a decent place for women and children, Hatton also attempts to win the affection of Abbie Irving (de Havilland), with whom he got off to a very rocky start. With a cast of excellent supporting actors including Ann Sheridan, Bruce Cabot, Frank McHugh, Victor Jory, Henry Travers, and Henry O’Neill, Dodge City is classic Western adventure Flynn and de Havilland style!

Santa Fe Trail (1940) is another Western outing for Errol Flynn and Olivia de Havilland. In this film, Flynn portrays “Jeb” Stuart while Ronald Reagan portrays George Custer, seven years before the Civil War begins and directly after their graduation from West Point. Along with several classmates, Stuart and Custer are sent out to the U.S. Cavalry’s “suicide station” in Ft. Leavenworth where they hope to free “bloody Kansas” from the abolitionist raids led by John Brown (Raymond Massey is sensational as the fanatical anti-slavery leader). The chase for Brown begins in Kansas, but eventually moves east to Harper’s Ferry, Maryland for the final showdown. Along the way, Flynn’s “Jeb Stuart” not only falls in love with de Havilland’s “Kit Halliday”, but is joined by Alan Hale and Guinn “Big Boy” Williams as humorous “wanna be” soldiers. Although much of the story is historically inaccurate, it is still wonderfully entertaining and rather thought-provoking, especially where John Brown’s motives and beliefs are concerned.

They Died With Their Boots On (1941), is the last of the Flynn and de Havilland pairings and was one of the top grossing pictures of 1941, despite its many historical inaccuracies. The film follows the life of George Armstrong Custer (Flynn) from West Point cadet, to Civil War general, to leader of the famous 7th Cavalry, to his disastrous defeat at the Battle of Little Bighorn. They Died With Their Boots On also shows the private life of General Custer and his abiding love for Elizabeth “Libby” Bacon Custer (de Havilland) until his battlefield death in 1876. The outstanding supporting cast includes veteran character actor Gene Lockhart, the very versatile Arthur Kennedy, and a young Anthony Quinn as Crazy Horse. As always, the chemistry between Flynn and de Havilland is in full force, making this movie another enduring classic by one of our favorite on-screen couples.

There is a ninth film in which both Flynn and de Havilland appear, but it is one of those studio extravaganzas that put all the major stars at Warner Brothers together for cameos or musical numbers. This was done to promote morale during World War II. The picture’s title is Thank Your Lucky Stars (1943) and although both Flynn and de Havilland are in it, they are appearing as “themselves” and not in the same scenes. We have never had the privilege of viewing this picture, but have enjoyed several films of this type in the past.

Trivia Question for Today: Can you name the amazing child actor in Dodge City who gets dragged by runaway horses while trying to help Abbie (de Havilland)? Check our next post for the answer. Don’t forget to read Let’s Talk Classic Movies every Monday, Wednesday, and Friday.

Trivia Answer for Previous Post: Olivia de Havilland’s younger sister is actress, Joan Fontaine, who won a best actress Oscar for Hitchcock’s Suspicion in 1941. (Fontaine has the distinction of being the only actor, male or female, who ever won an Oscar for a Hitchcock film.) Although both sisters are still living, they have sadly been estranged for many years.