On July 1, 2020, Dame Olivia de Havilland celebrated her 104th (!) birthday in Paris, France. Aside from being the last surviving cast member from Gone With the Wind, she is also one of the last surviving figures from the Golden Age of Hollywood. Olivia is a two-time Oscar winner, having won the Best Actress Academy Award for her roles in Hold Back the Dawn (1941) and The Heiress (1949). However, aside from being known for her age and status as an Oscar-winner, Olivia is probably best known for her nine (!) collaborations with the incomparable Errol Flynn.
Full Disclosure: I LOVE Errol Flynn.
In his autobiography, My Wicked, Wicked Ways*, Errol admits that he fell in love with Olivia during the making of his (and her) first big studio film, Captain Blood. However, despite his infamous reputation as a panty-dropping ladies man, Errol does not kiss and tell. In fact, he states that his propensity for playing juvenile pranks on Olivia probably lost him his chance at a relationship with her. Olivia on the other hand, admits that the two of them had some sort of passionate romance, however, their relationship was never consummated. What is the real truth? The only people who know that for sure are Errol and Olivia. Errol unfortunately is no longer around (passed in 1959) and Olivia is remaining tight-lipped on the subject.
*My Wicked, Wicked Ways is an amazing book. It, along with Desi Arnaz’ A Book, is the most entertaining book I have ever read. During my first read, when I got toward the end, I actually read just one page a night because I didn’t want it to stop!
What we do know is that on-screen, Errol and Olivia’s chemistry is off the charts.
Errol and Olivia appeared in the following films together:
Captain Blood (1935). Errol and Olivia’s big break. This film made an overnight matinee idol out of Errol and opened the doors for Olivia. Errol appears as the title character, Dr. Peter Blood aka “Captain Blood.” Peter is arrested for treason while treating a patient who participated in the recent rebellion. Peter is given a break (maybe?) and instead of execution (after being sentenced to death), he is sold into slavery. Peter, along with other future slaves, are shipped off to the West Indies.
Olivia appears as Arabella Bishop, the niece of the local military commander, Colonel Bishop. Arabella fulfills every woman’s fantasy and purchases Errol… err… Peter for 10 pounds to be her slave. You got one heck of a deal, Arabella. You will not be unhappy. Peter of course, resents being sold into slavery and is cold to Arabella. Eventually Peter and the other men revolt, seize a Spanish ship and become pirates.
Peter and Arabella’s relationship follows a similar trajectory that many film romances share. Boy meets girl. Boy and girl don’t get along. Boy or girl spend much of the movie trying to get the other to like them. They fall in love at the end. However, unlike most of the romantic fluff out there, Captain Blood is exciting, entertaining, and fun. Errol and Olivia’s playful flirtation and rapport is one of the big reasons for this film’s success.
The Charge of the Light Brigade (1936)
I’ll admit that I’ve only seen this film once. It features Errol and Patric Knowles as brothers living in India during the mid-19th century. Errol is a Major and Patric is a Captain with the 27th Lancers of the British Army. The main conflict is that Patric has betrayed Errol by taking up with his fiancee, Elsa, played by Olivia.
Much of this film features battles (blah) and the love triangle between Errol, Patric, and Olivia (ooh I love love triangles). However, the animal abuse by the film production crew, and Errol’s subsequent outrage is my biggest takeaway from this film.
In his autobiography, Errol details in length the cruel tactics used to make the horses trip for the battle scenes. An animal lover and accomplished horseman, Errol was disgusted and outraged by what he saw on set. He was further incensed by director Michael Curtiz’ nonchalant attitude toward the numbers of horses injured and killed by his stunts. Errol reported the production to the ASPCA. This action led to the US Congress implementing measures to ensure that animals used in film production were not injured or killed–thus the “no animals were harmed in making this motion picture” statement that is featured in most movies today.
The Adventures of Robin Hood (1938)
This is probably Errol and Olivia’s best known film collaboration, as well it should be. This film is perfect from start to finish. It is exciting, funny, has a great cast, fun characters, beautiful costumes, everything that one wants in a film. And this film, in its glorious Technicolor, is absolutely gorgeous.
I don’t think much plot is necessary, as most people, I imagine, are familiar with the Robin Hood legend. Errol plays the titular character, Robin Hood. Robin and his gang of merrymen have been banished to Sherwood Forest after opposing Prince John (Claude Rains)’s tax raise and voicing his opposition to Prince John’s usurping his brother, King Richard the Lionheart (Ian Hunter)’s throne and his intention to restore Richard’s place in the kingdom when he returns from fighting in the Crusades. Olivia plays Maid Marian and she’s disgusted by Robin’s insolence and vigilante behavior. She also doesn’t like that Robin and his gang regularly rob the rich to pay the poor.
However, as the film progresses, Marian begins to see Prince John for who he truly is, and also realizes that Robin is a good guy and begins to fall in love with him–much to the chagrin of Sir Guy of Gisbourne (Basil Rathbone).
Four’s a Crowd (1938)
This is one of Olivia and Errol’s lighter fare. After appearing in back to back swashbucklers, Flynn was eager to do something else. Warner Brothers appeased their star by placing him in this light comedy. Honestly, this isn’t the greatest film, but it has a fantastic cast, Errol looks great, it’s amusing, and it’s fun to see Errol in a comedic part. He shows a flair for comedy. It’s a shame that he wasn’t given more opportunities.
Olivia in this film is adorable, but honestly, her character is annoying. The best pairing in this film is Errol and Rosalind Russell.
In this film, Errol plays Bob Lansford, the former editor-in-chief of the local newspaper where Jean Christy (Russell) works as a reporter. Jean is concerned that her new boss, Pat Buckley (Patric Knowles) is running the newspaper into the ground. Since leaving the paper, Bob has formed a new PR firm. Jean appeals to Bob to return to the helm of the newspaper. While initially uninterested, Bob becomes interested in this prospect when he learns that Pat’s fiancee is Lori Dillingwell (Olivia). Lori is the granddaughter to John P. Dillingwell (Walter Connolly), a millionaire who has developed a poor reputation. Bob hopes to use Lori to gain access to John P. so that he can obtain his business for his PR film.
Errol is his usual charming self in this film. Olivia on the other hand, while pretty and adorable, acts like a giggly airhead and has an irritating laugh. Patric Knowles’ character isn’t much better. The two of them together can be a little annoying at times. However, if you love Errol and love Rosalind Russell (like I do), then they are worth the time spent watching this film. I’ve watched this film numerous times, so obviously Olivia and Patric’s characters don’t keep me away from this film too much.
Dodge City (1939)
I’m not a big Westerns fan, but I love this movie. In this film, Errol plays Wade Hatton, an Irish cowboy who has ties to Dodge City is enlisted by Colonel Dodge to clean up the town. It has been overrun by Jeff Surrett (Bruce Cabot) and his gang. Wade brings his friends, Rusty (Alan Hale) and Tex (Guinn “Big Boy” Williams) to assist. Olivia plays Abbie Irving, a settler who is traveling to Dodge City with Wade and his companions. She is planning on living with her aunt and uncle who reside in Dodge City.
After initially turning down the sheriff job, Wade agrees after witnessing the tragic death of a young boy in town. Wade, Rusty and Tex are doing a good job of clearing out the riff raff, but obviously are met with opposition by Surrett and his cronies. Abbie, meanwhile, has taken a job writing for the local newspaper, headed up by Joe Clemons (Frank McHugh).
Despite being a Western, I think this is a really fun film and Olivia and Errol once again light up the screen. Alan Hale is hilarious, especially when he inadvertently joins a temperance movement. Frank McHugh is always a delight.
Ann Sheridan’s talents and personality are wasted in this film. She appears in a small part as a saloon girl. Someone of Sheridan’s caliber was not needed for this role.
The Private Lives of Elizabeth and Essex (1939)
At this point in her career, Olivia was tired of playing Errol’s girlfriend in all her films (there are worse things you could be, imo). She wanted a chance to play more challenging parts and stretch her acting chops. She had just completed one of her most famous roles, Melanie in Gone With the Wind, and hoped that this was her chance for more meaty parts. However, Jack Warner, the bigwig at Warner Brothers was afraid that this experience would go to her head. To keep her grounded, he cast her in a small part in The Private Lives of Elizabeth and Essex starring Errol and Bette Davis.
‘Elizabeth and Essex’ is Bette’s film. Olivia’s part is so insignificant, that it could have been given to anyone and not made much of a difference. Olivia is completely lost in this film, especially in the shadow of Bette’s performance as Queen Elizabeth I. This film details Elizabeth I’s relationship with the much younger Lord Essex, played by Errol. While in love with Elizabeth I, Essex also yearns for power and is frequently at odds with his lover/Queen when he defies her orders. Elizabeth I struggles with her age, vanity, and her love for Essex, but also wants to retain her power.
Olivia plays Lady Penelope, Elizabeth I’s lady in waiting. The main conflict with her character is that she’s in love with Essex as well. Elizabeth I fears losing Essex to the much younger and prettier Penelope. Penelope also schemes to break Elizabeth I and Essex up so that she can pursue him. This could possibly be a meaty part, but Bette’s performance as Elizabeth I is so intense and, frankly, it’s A LOT, that one almost forgets that Olivia is even in the film until she’s seen again.
While I love Bette, I cannot decide if I like this performance. Sometimes I think it’s amazing and other times, I can’t get past Bette’s constant fidgeting. What does make this film worth watching are the gorgeous costumes, a young Nanette Fabray in her film debut, and Errol’s thigh-high boots.
Santa Fe Trail (1940)
This film must be Errol and Olivia’s least popular. I only say that because this film is in public domain. As far as I know, it’s never received a proper studio release. I’ve only seen it a couple times, it’s not bad, but it’s not my favorite either.
In this film, Errol plays Jeb Stuart, a recent West Point graduate. He, along with his friend George Custer, played by Ronald Reagan, are sent to Fort Leavenworth, the most dangerous assignment in the Army. Both Jeb and George relish this assignment. On the way to Kansas, Jeb and George meet Cyrus Holliday who is building the railroad to Santa Fe, NM. His daughter, Kit, played by Olivia, is also accompanying him. Both Jeb and George are smitten.
Most of the remainder of the film features Raymond Massey as the villain, John Brown, and lots of battles and such. I don’t really remember the particulars.
They Died With Their Boots On (1941)
This is technically Olivia and Errol’s last film together. They have a very fitting goodbye scene toward the end of the film. While Errol’s dialogue is given within the context of a husband (who knows he will most likely die) saying a final goodbye to his wife (who knows deep-down that she won’t see her husband again), the words could apply to Errol and Olivia as well.
“Walking through life with you, ma’am, has been a very gracious thing.”George Custer (Errol Flynn) to wife, Elizabeth Bacon Custer (Olivia de Havilland)
In this film, Errol plays General George Custer. At the beginning of the film, he is arriving at West Point in a ridiculous uniform that he designed himself, with the intention of looking like a visiting foreign general. While at West Point, George racks up a series of demerits for pranks and general disregard for any protocol and rules. Despite being at the bottom of his class, George and his class graduate early so that they can report immediately to Washington, D.C. at the onset of the Civil War.
Prior to graduation, George had met Libbie Bacon (Olivia) when she approached him, asking for directions. He asks her out on a date, but is unable to meet up with her when he is forced to report to DC for his war assignment. When they finally meet up again, George has made himself very unpopular, after making a joke at Libbie’s father’s expense. Libbie and George have to meet up in secret. Libbie’s maid, Callie (Hattie McDaniel), helps the couple keep their secret.
Through a miscommunication with the War Department, George is mistakenly promoted to Brigadier General. Despite this however, his regiment, the Michigan Brigade, wins at Gettysburg.
The remainder of the film features George and Libbie’s lives leading up to that fateful day at the Battle of the Little Bighorn, where the audience knows George will meet his fate.
This is a very sweet film, though not one that I re-watch very often. War and Westerns aren’t my favorite genres, but Errol and Olivia and Hattie make this film very re-watchable. Errol’s appearance at he beginning in his outlandish military garb is hilarious.
Thank Your Lucky Stars (1942)
Errol and Olivia appeared in this film together, but they weren’t together. Both appeared as themselves in separate numbers. Thank Your Lucky Stars was made during WWII and created to serve as a fundraiser for the war effort. Every star who appeared in the film donated his or her salary to the Hollywood Canteen.
The Hollywood Canteen was an organization opened by Bette Davis and John Garfield. It was intended to serve as a club that catered only to servicemen fighting in WWII. In addition to the US servicemen, servicemen of Allied forces and women in any branch of service were invited to attend. The idea of the Hollywood Canteen was that servicemen (and servicewomen) could enter the club using their uniform as a ticket. All amenities within the club were free. The club was staffed by countless members of the entertainment industry. Everyone from the big A-list stars down to the key grips volunteered to work at the Hollywood Canteen. A serviceman could enter the canteen and have Rita Hayworth serve him lunch, only to dance with Betty Grable afterwards.
The plot of Thank Your Lucky Stars is very thin. Basically, Edward Everett Horton and SZ Sakall are trying to stage a “Cavalcade of Stars” wartime charity show, but star Eddie Cantor’s ego is threatening to take over the production. Aspiring singer Tommy (Dennis Morgan) and his songwriter girlfriend, Pat (Joan Leslie), conspire to join the production by coaxing Horton and Sakall into replacing Cantor with their look-a-like friend, Joe.
Throughout the initial part of the plot, Hollywood stars like Humphrey Bogart make non-musical appearances. At the end of the film, we’re treated to what is presumably Horton and Sakall’s “Cavalcade of Stars.” It is in this section where we’re treated to Olivia and Errol’s only on-screen musical performances. They do not appear in the same production number. Olivia is paired with Ida Lupino. Honestly, their number isn’t really that great. Errol on the other hand, has a solo number and his song is one of the best in the show. His natural charisma and good looks are on full display, despite the silliness of the number.