We Love Pirates Blogathon: Errol Flynn’s Pirate Films

Of course I’d pick the blogathon button with my boyfriend, Errol Flynn (This photo is from “The Sea Hawk”)

Ah Errol Flynn. My boyfriend, Errol Flynn. While proved himself an adept actor in dramas, comedies, sports films, adventure… He’s best known today for his swashbucklers. Many of Flynn’s swashbuckler films involved him wielding a sword, such as in Captain Blood, The Sea Hawk, The Adventures of Don Juan, Against All Flags, and his best-known film, The Adventures of Robin Hood. In Flynn’s films, he always played the rogue hero. A man who displayed massive amounts of bravado and heroism, but could also make women weak in the knees with one flash of his megawatt smile. Flynn could swagger into the room and cut the villain down to size with one cutting remark. He always played a charismatic leader, one whom others looked up to and wanted to support. In this article, I’m going to focus on Flynn’s pirate films, it is Pirate Week, after all.

Two great stars are born in “Captain Blood,” Errol Flynn & Olivia de Havilland

Captain Blood (1935). This film was Errol Flynn’s big break. While he’d appeared in two films prior to Captain Blood, in one film, he played a corpse (The Case of the Curious Bride) and in another (Don’t Bet on Blondes), he had the small role as a boyfriend–nothing that was going to catapult him into stardom. For ‘Blood,’ Warner Brothers had wanted to cast Robert Donat, but he turned the film down, fearing that it’d be too strenuous for his asthma. Finally, the studio settled on the unknown Australian, Errol Flynn, and cast him alongside the equally unknown, 19-year old Olivia de Havilland. This would prove to be a monumental film for both actors.

While I’m not in love with his hair, I would pay 10 pounds to have Errol Flynn be my slave.

In this film, Flynn plays the titular, Captain Peter Blood, a 17th century British doctor who is arrested and accused of treason against King James II after treating Lord Gilroy. The judge sentences him to death, but the King sees an opportunity for profit, and opts to transfer Peter and other rebellious men to the West Indies to be sold into slavery. After landing in Port Royal, the men are put up on the block to be sold to the wealthy landowners. When it’s Peter’s turn, he is purchased for 10 pounds by Arabella Bishop (Olivia de Havilland), the wealthy niece of the local military commander, Colonel Bishop. Arabella is charmed by Peter’s rebellious nature and let’s face it, he was the most attractive of all the slaves. Peter resents having been purchased like he was a piece of meat. To improve his situation, Arabella recommends Peter for the job of her uncle’s personal physician. It seems that Colonel Bishop suffers from the gout. The conflict of the film occurs when Peter puts together a plan for himself and his fellow slave men to escape. They do and thus begin their life of piracy.

Errol Flynn in a costume test for “The Sea Hawk.” He looks a little mangy, but I wouldn’t turn him down

The Sea Hawk (1941) In this pirate film, Flynn plays Captain Geoffrey Thorpe, a British subject of Queen Elizabeth I (Flora Robson). He and his crew capture a Spanish ship, helmed by the Spanish Ambassador, Don Alvarez (Claude Rains), who along with his daughter, Dona Maria (Brenda Marshall), were sent to Britain by King Phillip II of Spain, to quell Elizabeth I’s suspicions that he’s trying to put together an Armada Fleet. However, after Thorpe captures their ship, he takes Don and Dona to Britain with him. And because he’s ladykiller Errol Flynn, Thorpe wins the affections of Dona Maria by returning her jewelry that he and his crew had stolen. While Queen Elizabeth I doesn’t approve of Thorpe’s crew’s activities as it endangers Britain and Spain’s peace treaty, she hesitantly allows Thorpe to go forward with his plan to seize a Spanish Treasure Fleet.

See? Errol Flynn and his monkey. This really was Flynn’s pets. He loved all animals and had quite the menagerie at his home

At one point in the film Flynn and his crew are captured by the Spanish and made to work as slaves in the Galley. They are chained to each other and to the boat and forced to provide the ship’s power. Let me just get this out of the way: I am here for scantily-clad slave Errol Flynn. Of course, the men need to figure out a way to escape. Later, Flynn charms Queen Elizabeth I with his monkey (no, that’s not a euphemism. He really does have a monkey) and continues to woo Dona Maria. This is a really great film, probably Flynn’s best pirate film, in my opinion. I wish they’d cast a leading lady with a little more personality, as Brenda Marshall is a little bland, but over all, she is fine. Flora Robson is also much more effective as Queen Elizabeth I, than my personal Queen, Bette Davis. Yes, I said it.

Against All Flags (1952). This film features an older Errol Flynn. No he’s not has lithe as he was previously. He’s a little more haggard. He isn’t quite the same vivacious Errol Flynn of the past as his demons were quickly catching up with him; but because it’s Errol Flynn, he is still attractive and still has panache. In this film, Flynn plays Lieutenant Brian Hawke, who works aboard the British ship, The Monsoon. He volunteers for a dangerous mission to infiltrate the pirate’s base on the coast of Madagascar. He plans to pose as a deserter. When Hawke arrives at the pirates’ base, he immediately arouses suspicion in Captain Roc Brasillano (Anthony Quinn). Brasillano says that he will bring Hawke in front of a pirates’ council to decide his fate. If they don’t like him, he’ll be executed.

Maureen O’Hara and Errol Flynn in “Against All Flags”

At the same time, because it’s Errol Flynn, he’s attracted the attention of Spitfire Stevens (Maureen O’Hara), the only female pirate aboard ship. She is one of the Captains of the ship and inherited the position from her father. At the council, Hawke ends up dueling one of the pirates and winning. He’s invited to join the pirates on a tentative basis, as he still needs to prove his worth. At some point, after taking over another ship, another woman is taken on board. She becomes immediately smitten with Hawke, much to the chagrin of Spitfire, even though she pretends not to like Hawke. Eventually, because it’s Errol Flynn, he ends up in a love triangle with himself, Brasillano and Spitfire, with an offshoot of a small triangle between himself, the other woman, and Spitfire. Hawke himself has no interest in the other woman, he only has eyes for Spitfire.

This is a beautiful looking film. One cannot go wrong with Maureen O’Hara. She was also known for her pirate films. It is definitely a treat to have two major figures of Pirate Cinema: Flynn and O’Hara, in the same film.

Has anyone looked better in Technicolor than Maureen O’Hara? The woman in pink is the “other woman” who is in love with Flynn. We’ll just ignore whatever is going on with Flynn’s hair, and focus on his great costume!

Claude Rains Blogathon- “The Adventures of Robin Hood” (1938)

I love Claude Rains. He definitely deserves to be more well-known. He appeared in just as many important films as his peers who attained “legend” status long after their passing. Perhaps it’s because he doesn’t have the typical leading man good looks. He was short. But so was Edward G. Robinson, and he’s considerably more well known than Rains. For the record, while I wouldn’t say that I found Rains “hot,” in some films, I think he’s quite attractive. And that voice!

Rains played the leading role in films like Mr. Skeffington, The Invisible Man, The Unsuspected, Here Comes Mr. Jordan, and The Clairvoyant. And he often played the supporting lead in A-list films like: Casablanca, Now Voyager, Notorious, Mr. Smith Goes to Washington, and my personal favorite, The Adventures of Robin Hood.

Prince John (Claude Rains) tries to butter up Maid Marian (Olivia de Havilland)

The Adventures of Robin Hood, while a career-defining role for stars Errol Flynn and Olivia de Havilland, it was also a remarkable role for Rains. As Prince John, Rains deviates from his typical sophisticated, dignified persona. Prince John is a despicable villain, drunk with power, eager to rob his subjects blind while his brother, King Richard the Lionheart, is fighting in the Crusades.

Claude Rains as Prince John assumes King Richard’s place on the throne.

Rains’ Prince John is quite flamboyant and a bit of a dandy. He is vain and wears a red-Prince Valiant-style haircut and flashy medieval garb with large embroidered velvet capes and bright colors. He enjoys sitting on Richard’s throne, holding Richard’s scepter. Prince John is a horrible person, very sadistic. He arranges an entire archery tournament with the sole purpose of luring Robin Hood out of hiding and setting up his execution. Prince John seems to relish watching “The Tall Tinker” (i.e. Robin Hood) and the other contestants shoot arrow after arrow, knowing that he’ll have his man at the conclusion of the tournament.

Despite how horrible Prince John is, Rains imbues him with so much panache and so much life that not only is it fun to watch Prince John attempt to ruin the Saxon’s lives, but it’s also fun to watch Robin Hood get the best of him each and every time. Prince John is hilarious, such as the scene when Robin Hood enters the banquet hall with one of Prince John’s royal deer (deceased) draped around his shoulders. I love the scene when Prince John is so excited to see “The Tall Tinker.”

Prince John (Claude Rains) (center) admires his striking Prince Valiant hairdo while The Sheriff of Nottingham (Melville Cooper) (left) and Sir Guy of Gisbourne (Basil Rathbone) (right) look on in bemusement.

Then of course, Prince John’s undoing at the end of the film is fun to watch as well. For someone who let power go to his head so fast and so hard, he sure gave up easily when Richard banishes him. If one wants to see Rains give a performance like no other, then watch The Adventures of Robin Hood. Plus, you’ll get to see the lovely Olivia de Havilland and my boyfriend, Errol Flynn.

Robin Hood (Errol Flynn) makes his triumphant entrance carrying one of Prince John’s prized royal deer.

In Memoriam: Dame Olivia de Havilland 1916-2020

Olivia, looking amazing

Just a few weeks ago, I participated in the Olivia de Havilland blogathon, celebrating her 104th birthday on July 1. In that post, I discussed her nine films with her most frequent co-star, the gorgeous Errol Flynn. It brings me great sadness to have to write a memorial post about Olivia. Last weekend, she passed away in her sleep of natural causes in her Paris townhouse at the age of 104.

While this news is not unexpected, I cannot help but feel sorrow over Olivia’s passing. She was the last surviving major Hollywood star from the golden age. When I was growing up in the mid-80s through early-00s, many of the classic Hollywood stars were still alive. Some were even still working! While I am too young to remember the passings of Fred Astaire and Rita Hayworth in 1987 (I was in preschool then), and thank god I wasn’t aware of Lucille Ball at the age of 5 when she passed in 1989 (if that had happened just a few years later, or even now, I would have been devastated). I remember being in middle school when Gene Kelly, Ginger Rogers, Robert Mitchum, and James Stewart passed.

Olivia and sister Joan Fontaine

People like Katharine Hepburn and Bob Hope were old when I was born, they were still old throughout all of my formative years. When they both died within a month of one another, I was sad as they were enduring symbols of old Hollywood, immortal as far as I was concerned. Kirk Douglas was always there. Doris Day was too. Joan Fontaine seemed like she would last forever. Shirley Temple was just a child! Surely she would be around forever. Then, there was my queen, Olivia de Havilland.

Now, they’re all gone.

It is moments like this when people start making lists of people from the Golden Age who are still alive. I cannot bring myself to make such a list. To me, that seems like bad luck. It seems like chronicling those who are blessed with longevity is just asking to have a hex placed on them. So I will refrain.

Olivia, looking fierce

Olivia de Havilland’s death represents the final door closing on the Golden Era. She was the last tangible link to this amazing period of filmmaking where everything was in its infancy, numerous techniques, camera angles, acting styles, etc. were pioneered every day during this period of great innovation. Olivia de Havilland was a woman who could recall working with people like: my boyfriend Errol Flynn, Montgomery Clift, Clark Gable, Vivien Leigh, the amazing Hattie McDaniel, James Cagney, Rita Hayworth, Rosalind Russell, Dick Powell, Charles Boyer, Bette Davis… legendary Hollywood personalities who had long since passed.

Olivia had an infamous feud with her sister, Joan Fontaine. It’s a shame that the two ladies could not get along and share their respective good fortunes with one another, but that isn’t anyone’s business but Olivia and Joan’s. What was the feud about? Who knows? Both ladies must have had their reasons.

Can you imagine if What Ever Happened to Baby Jane? had been made with Olivia and Joan instead?

Olivia was also not afraid to put herself on the line to speak out about perceived injustices both she and her peers faced. In 1943, Olivia sued Warner Brothers for violating California Labor Codes. During the early days of the studio system, contract players were signed to seven-year contracts. The studios viewed actors as employees, they were no different than the cameraman, the set designer, the electricians, or the propmen. The actors would be assigned to specific projects and were expected to fulfill their end of the contract and make the film.

L to R: Hattie McDaniel, Olivia, Vivien Leigh in “Gone with the Wind.”

However, many of the performers believed that they should have a say over their projects–especially if their appearance in a film was proven to make money for the studio. Many actors, such as Bette Davis, were trying to hone their craft and also take on challenging parts. These performers didn’t want to hurt their box office clout and essentially, their marketability by taking on crappy parts. The studios believed that they were allowed to suspend actors for refusing parts. Then, after the film was completed with a different actor, the length of the production time would be added to the actor’s existing contract.

In 1943, Olivia reached the end of her 7-year contract at Warner Brothers. She was then informed that she owed them an additional 6 months time to make up for the parts she refused. Olivia sued Warner Brothers to be released from her contract and won the lawsuit! Warner Brothers tried to appeal, but lost. The California Superior Court upheld the “seven-year contract” labor ruling and named this law the “de Havilland Law,” a law that is still in place today. Even sister Joan Fontaine gave Olivia kudos stating “Hollywood owes Olivia a great deal.”

Of course, Warner Brothers, being petty, managed to get Olivia blacklisted in Hollywood for two years.

In 1945, Olivia signed a two-picture deal with Paramount. She immediately went to work on To Each Her Own.

She won the Best Actress Oscar.

Olivia as Catherine Sloper in “The Heiress.”

In 1949, Olivia made The Heiress with Montgomery Clift. I just watched this film the other day. I’d seen it once prior, but didn’t really remember much about it, except for the ending. Olivia’s performance in this film is nothing but fantastic. Her transformation from meek, proper, shy Catherine to a cynical, bitter, hardened woman is nothing short of remarkable. Not only does Olivia’s portrayal change, but her entire look, her voice, the way she carries herself, everything changes. I absolutely loved it.

Olivia won a second Best Actress Oscar for her performance in The Heiress.

In the 1950s, Olivia moved to Paris, married, had two children, and continued her film career and started appearing in the theater and on television. Her career continued until 1988 when she retired. From then on, Olivia stayed active appearing in various career and film retrospectives. As the last surviving major cast member (since 1967, with the death of Vivien Leigh) of Gone With the Wind, Olivia served as an ambassador for that film. She also received numerous accolades and honors, including being appointed Dame Commander of the Order of the British Empire by Queen Elizabeth II.

Goodbye Olivia. We will miss you.

I will miss Olivia immensely. Knowing that she was still alive, healthy, and active was such a consolation–the Golden Age of Hollywood was alive and well. Now, another piece of it is gone. However, Olivia has achieved immortality. Her films, along with everyone else’s, will live on forever.

We’ll always have Paris.

Olivia de Havilland Blogathon!

Errol Flynn and Olivia de Havilland (aka “the luckiest woman in the world”)

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.

Errol and Olivia in “Dodge City.”

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 fulfills my fantasy and purchases Errol (for 10 pounds!) to be her slave in “Captain Blood.”

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.

Patric Knowles, Olivia, and Errol in the love triangle in “The Charge of the Light Brigade.” Olivia looks confused. Duh girl, pick Errol.

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.

Olivia and Errol in “The Adventures of Robin Hood.”

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.

Patric Knowles, Olivia, Rosalind Russell, Errol in “Four’s a Crowd.”

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.

Olivia and Errol 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.

Errol and Olivia in “The Private Lives of Elizabeth and Essex.”

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.

Olivia and Errol in “Santa Fe Trail.”

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)
Errol and Olivia in their last ever scene together in “They Died with Their Boots On”

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.

Olivia, George Tobias, and Ida Lupino perform “The Dreamer” in “Thank Your Lucky Stars.”

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.

Errol sings “That’s What You Jolly Well Get” in “Thank Your Lucky Stars.”