Bob Hope And Bing Crosby Were The Perfect Pair, But They Weren’t Always Pals Behind The Scenes

To generations of moviegoers, Bob Hope and Bing Crosby will be forever remembered as best buddies. Because over several decades they established a cinematic partnership that would go down in legend. But when the cameras were turned off, things were quite different. And the slaps on the back, chuckles and smiles between the two on the screen, didn’t necessarily translate off of the screen.

It’s easy to understate nowadays but Hope and Crosby were both genuine titans of the entertainment industry. As a comedic pairing, they were one of the most successful double acts in cinema history, ringing in huge box-office receipts. But in their own ways, they also helped lay the groundwork for stand-up comedy and big band singing.

PBS’ American Masters credited Hope in 2017 with being the man who invented stand-up as it is today, for example. He came out of the vaudeville scene in the 1920s. But while there were comedians before him, his act was new in that it addressed events of the day and had a spontaneous, off-the-cuff approach. “The modern stand-up comedy monologue was essentially his creation,” PBS said. So what about Crosby’s impact?

According to NPR in 2013, “Bing Crosby’s influence on modern singing is so huge, we barely notice it anymore.” His style, which adopted a “laid back jazz influence,” made him a star so massive that even a young Frank Sinatra was his biggest fan. And at the height of his powers Crosby had an astonishing 50 million people listening to him on the radio every week.

Yet despite being two of the most popular entertainers of all time, both Hope and Crosby left complicated legacies. In 2014 Richard Zoglin published the biography Hope: Entertainer of the Century, which included some bombshells about Hope’s private life. He reportedly cheated on wife Dolores countless times during their marriage, for one thing.

Zoglin told the Express newspaper, “Bob Hope had affairs with chorus girls, beauty queens, singers and showbiz wannabes up into his 70s. He had a different girl on his arm every night. He was still having affairs into his 80s.” Zoglin claimed that Dolores knew full well what her husband was doing but had an arrangement with him.

“Dolores came to an understanding with Hope,” said Zoglin. “He could play around as long as he never brought his mistresses home and never embarrassed her publicly.” Zoglin added, “He had women in every port. He had affairs with Ethel Merman and Doris Day, but usually it was not his co-stars but starlets that he bedded.”

And Hope’s serial infidelity, coupled with the fact that he was always travelling for work, made him an absentee father. Zoglin said, “It was hard for all his children. They felt his absence. He just wasn’t home much. And when he was home, it felt more like a star visiting, rather than a loving father. He was always emotionally detached and insular.”

Even regarding his legacy as an entertainer, in some eyes Hope became a dinosaur who clung to the public eye for too long. In the 1970s his old fashioned views clashed with those of the younger generations. As Zoglin told Terry Gross on the Fresh Air podcast, “Bob Hope was the establishment. Bob Hope was friends with Nixon.”

Hope spoke out in favor of the Vietnam War, and was disparaging about the feminist movement, the LGBT community, and racial minorities. Zoglin admitted, “He was clueless at that time.” Hope, overall, had become a powerful man, and this made it harder and harder for him to be a relevant comedian in his later years. Because, after all, a comedian’s job is usually to skewer those in power.

Hope died in 2003 at the age of 100, meaning he long outlived his co-star Crosby, who passed in 1977. Crosby’s reputation would take a hit posthumously, too, when his son Gary wrote a tell-all 1983 autobiography called Going My Own Way. Within its explosive pages, he accused his father of both physically and mentally abusing his children.

But Philip, another of Crosby’s sons, denied these claims, saying, “My dad was not the monster my lying brother said he was. He was strict, but my father never beat us black and blue, and my brother Gary was a vicious, no-good liar for saying so.” He did admit that Crosby believed in corporal punishment when it came to child-rearing, though, yet this wasn’t uncommon for the time.

While Zoglin’s biography wrestled with the difficult aspects of Hope’s life and career, the author also paid tribute to his remarkable on-screen partnership with Crosby. In their much loved Road film series, they usually played con men on an adventure in a far-flung exotic location. It was here that they did things no one had ever seen on-screen before.

Because in the movies Hope would regularly break the fourth wall by looking at – and speaking to – the audience. He would even reference Hollywood censors, and had a running gag in which he over-acted in an attempt to win an Oscar. This approach to filmmaking was unheard of in the 1940s, and it would have been incredibly exciting to watch.

Plus Hope and Crosby took a semi-improvisational approach to the jokes in the Road movies. While they didn’t make things up on the spot, they did try different takes on the gags and would see which ones worked out best. This idea of the script being turned around was, again, unheard of back then.

So while Hope and Crosby’s off-screen lives came to be questioned in later years, their time as movie stars was unimpeachable. When he appeared on Fresh Air, Zoglin began by recounting how the two entertainers first linked up. He revealed, “Bob worked with Bing for the first time in 1932 at the Capitol Theater in New York.”

Crosby was the bigger star at the time, and he was headlining the show at the Capitol Theater solo. Zoglin said, “They actually, to entertain themselves, they just decided to do some bits together on-stage. Just some funny, silly little bits together. And they worked so well together – they really loved working together.”

But the pair weren’t positioned to capitalize on their duo potential straight away. As Zoglin revealed to Fresh Air, “Then they didn’t see each other for five years because Bing went back to Hollywood where he was making movies and Bob stayed on Broadway for another five years.” They did reconnect, however, when Hope moved to Hollywood after signing up to star in The Big Broadcast of 1938.

“When Bob went out to Hollywood in 1937, he got friendly again with Crosby on the Paramount lot and they became good friends,” explained Zoglin. Yup, the two began entertaining as a duo at the Del Mar racetrack, which Crosby co-owned with other actors, including Oliver Hardy and Gary Cooper. It was here that Paramount executives saw the potential of the pairing.

Zoglin revealed that, as soon as the execs saw Hope and Crosby trading jokes on-stage, they said to themselves, “Hey, these guys might work together in a movie.” This led to their first film collaboration, Road to Singapore, which became a huge hit in 1940. It spawned the long-running Road franchise, with the seventh and final entry hitting screens in 1962.

As Zoglin explained to Fresh Air, “The audience responded instantly to the chemistry of the two of them on-screen together. They were relaxed, informal – they seemed to be friends authentically, not just movie characters.” He added, “Nobody thought it was going to be anything more than a one-shot when it was made, but it became the first of what was probably the greatest buddy series in movie history.”

The Road series crystallized the screen personas of Hope and Crosby in the eyes of audiences. Zoglin explained, “Bob was kind of the patsy, the nervous guy, the guy who chased women but never got them. He was always afraid. His sort of cowardly character was really developed there.”

By contrast, “Bing was the cool customer, the schemer, the guy who always got the women. So, there was this comradery, but this rivalry. It had tension, but it had real affection. It was just a terrific combination.” Yet the relationship between Hope and Crosby in real life, sadly, seemed to have far more tension than affection.

Zoglin admitted to Fresh Air that, while the two men were friends off-screen, they weren’t close by any stretch of the imagination. He explained, “They were very different personality types, not – they were clashing in a sense – not in the way they were in the movies, but in this sense.” The biographer then explained the fundamental difference in Hope and Crosby’s personalities.

“Bob was someone who loved being famous and loved being out there as a star,” said Zoglin. “And he loved talking to fans, and he was basically a happy guy. Bing was much more ambivalent about his stardom, I think. He was more reclusive. He didn’t like the Hollywood scene. He moved up to Northern California halfway through his career.”

Crosby reportedly hated having to attend Hollywood events, and there was one in particular where his absence hurt Hope. As Zoglin revealed to Fresh Air, “There was a famous Friar’s Club roast for Bob Hope in the late 1940s, and every major, you know, comedy star from, you know, Milton Berle, George Jessel etc were there on the dais. Bing was supposed to be there, and he didn’t show up.”

This wasn’t the only time that Crosby’s cold aloofness bothered Hope. According to Zoglin, Hope told a colleague later in life that Crosby never once invited he and wife Dolores for dinner at his home. Considering they knew each other for so many years, it’s understandable that Hope was upset by that.

“You know, I think there was a little – a slight bit of resentment there,” admitted Zoglin. “And I think, also, Bob envied Bing in the early years, particularly. Bing was more successful, and Bing was a smart businessman. Bob learned a lot from him. And I think that there was a little bit of a rivalry, and maybe some of that rivalry is reflected in the Road pictures.”

Despite these elements of conflict, though, Zoglin was quick to point out that the two men still sought to collaborate until late in their careers. He said, “But, you know, the bottom line was they loved working together. They kept trying to work together, even to the end.”

“There were seven Road pictures,” continued Zoglin to Fresh Aid. “The last one was made in 1962 and probably shouldn’t have been made because it wasn’t very good.” Yet Hope and Crosby were still trying to get an eighth instalment off the ground in 1977, but then Crosby passed away. Zoglin felt, “Any team that, you know, enjoys working together that much is pretty great.”

Yet Zoglin reflected more bluntly on Hope and Crosby’s relationship when he spoke to the Express newspaper in 2014. He said, “They were not close friends and even when living nearby they rarely socialised. Bob told a friend he simply didn’t like Bing very much.” He then claimed that their long time Road co-star Dorothy Lamour grew to hate both men.

“Bob and Bing formed a production company in 1947 to produce subsequent Road movies and didn’t include Lamour in the deal,” revealed Zoglin. “She was very upset. When the last Road movie was filmed in 1961, Bob and Bing decided Lamour was too old, even though she was younger than both of them, and hired Joan Collins instead, giving Dorothy just a small cameo.”

Perhaps this is an illustration of how, even though they weren’t best pals in real life, Hope and Crosby were savvy enough to keep their working relationship close. Together they were industry-conquering heroes, so they saw to it that they were in control of the Road movies. But it came at their female co-star’s expense, unfortunately.

There was another thing that united the two men aside from their work, though. They both adored golf. And Bing was the better player by most accounts, with a handicap of three compared to Hope’s eight. The two would play exhibition matches with each other for charity, which routinely raised thousands of dollars.

Indeed, when Crosby died of a heart attack it was while on a golf course in Spain. Then when Hope wrote a tribute to his co-star, it came in the pages of his 1985 book Bob Hope’s Confessions of a Hooker: My Lifelong Love Affair with Golf. Despite any private resentments that may have existed, Hope wrote warmly about Crosby.

Hope stated that when he heard of Crosby’s passing, “The shock and sorrow were so overwhelming I couldn’t describe it.” He was so shaken that he canceled his appearance at a show that evening, a rare thing for him to do. He had been in New Jersey for the show but flew home to California immediately.

The iconic comedian wrote in Bob Hope’s Confessions of a Hooker: My Lifelong Love Affair with Golf, “I knew that Bing, despite the fact he had still been very active, was not in the best of health.” He then described hearing about how Crosby defied doctor’s orders to do what he loved. Hope wrote, “Sometime after his death I heard that a doctor in England told him to play only nine holes because of his heart.”

“Bing had finished 18 that day,” continued Hope, “and was walking up the hill to the clubhouse when he collapsed and died. A part of my life went with Bing. I still miss him and always will, just like the rest of the world. I remember the good times with him, and they’ll be with me always.”

So while Hope and Crosby mightn’t have been as close as they appeared, there was still a lot of affection between them. And while there were things that divided them, too, this is hardly unusual for entertainers from Hollywood’s Golden Age. Plus it’s their cinematic output that will live longer in the memory when compared to anything else.

In 2020 The Guardian reviewed Road To Bali when it began streaming on Amazon, and highly praised the double act. “Hope and Crosby are a match made in Hollywood heaven,” wrote Stephen Snart. “As much as there’s an ongoing rat-a-tat competition between the two characters, there’s a sweetness to their relationship, which one can imagine is true of the performers as it is the characters.”