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Bob Hope & Bing Crosby’s Inappropriate Relationship

Comedy duos have been a mainstay of the entertainment industry since around the 1940s. On any given evening back in the day, you could flip on the tube to see the likes of Abbott and Costello meeting up Frankenstein. Or the rag-tag team Laurel and Hardy accidentally stumbling upon a hoard of German spies. But for smart-alecks, or really just about anyone with a crush on actress Dorothy Lamour. There was only one comedy team that really mattered: Crosby and Hope.

From 1940 to 1962, Bing Crosby and Bob Hope banded together to star in seven ‘Road to‘ films including hits like Road to Singapore, Road to Zanzibar, and Road to Utopia which were all met with enthusiastic reviews and broke box office records. Even to this day, that beloved franchise is still remembered as being ‘curiously modern’. And for being the spiritual grandfather of meta-comedy.

The AV Club once humorously quipped that anytime a comedian or musician winks at the character. Or puts on a front to look cool for the room that both the Hope and Crosby estates should paid a nickel.

Beyond their cash-cow film franchise, Crosby and Hope are remembered for their countless contributions to the world of cheesy Christmas music as well as the TV emcee industry. For one thing, Crosby’s recording of ‘White Christmas’ still holds the honor of being the best-selling single of all time. In fact, it’s estimated that 50 million copies have sold globally. And can you guess who holds the record for hosting the most Oscar ceremonies? Well, our boy Bob Hope has taken the reigns on that annual event a whopping 19 times.

Crosby and Hope adored by what’s been called the Greatest Generation. They were more than just media personalities. They were cultural heroes. It’s just a shame that there was nothing very delightful or whimsical about either of those men in their lives off the set and stage. Join Facts Verse to know more the details about Bob Hope & Bing Crosby’s Inappropriate Relationship.

From Nobodies to Superstars 

Crosby and Hope were born just weeks apart in 1903. But they were both on very different paths when they first joined hands to form their legendary comedy team. Crosby had aspirations of becoming a successful singer and actor. But his career was sitting at a standstill while he was trying to figure out what his next move might be.

Hope on the other hand was a rising comedy star who was just starting to hit his groove. The duo got their first chance to work alongside each other on stage at New York’s Capitol Theater in 1932. But it wouldn’t be until they showed off their material in front of a Paramount exec six years later that their first film together, Road to Singapore, given the greenlight.

It such a massive hit with audiences and critics alike that it given four sequels: Road To Zanzibar, Road to Morocco, Road to Utopia, and Road to Rio. Which all hit theaters in the 1940s.

While Paramount was busy coming up with new exotic locations for it’s wildly popular comedy team. Hope was busy chasing after women who weren’t his wife, Delores. Poor Delores.

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And don’t you dare think about going anywhere just yet. Stick around to find out what Crosby’s own son had to say about his father. You won’t believe what he revealed about the comedy icon.

Hope’s Many Mistresses

Hope’s lifelong obsession with chorus girls was an open Hollywood secret. In a hard-hitting critical Biography of his life, Groucho Marx son Arthur asserted that Bob Hope made love to more beautiful women in his lifetime than Errol Flynn. Arthur’s apparently studly Uncle Chico, and Bing Crosby combine.

Some of the women that he would bed were girlfriends like Marilyn Maxwell who was in his presence so often that folks started referring to her as ‘Mrs. Hope’. A lot of his other sexual exploits were just one-night stands. But Hope’s publicity team had one major mandate to contend with. They had to do everything in their power to keep everyone happy, paid off, and out of the press. And that task wasn’t always the easiest to pull off.

Hope shed away from sharing the intimate details of his many affairs. But he still spoke freely about his backward views towards women. In late 1970, NBC aired a shocking hour-long special called ‘Bob Hopes Looks at Women’s Lib’. And in it a lady network chief can seen dusting off the furniture before canceling the Indianapolis 500. And that’s precisely how Hope envisioned a woman in power to behave – impulsively and irrationally. 

Hope also shared some of his misogynistic views during the 1970 Miss World Beauty pageant. Hope kicked off the evening by comparing women to cows. But he took things to a whole new level when he got downright hateful after feminist protesters threw stink bombs in the middle of the event.

He told the media later that evening that ‘pretty women’ don’t involve themselves in the women’s liberation movement because they ‘don’t have those kinds of problems. Join Facts Verse to know more the details about Bob Hope & Bing Crosby’s Inappropriate Relationship.

Hope Alienated His Supporters With His Political Views

Around this same time, members of the press started quizzing Hope about his stance on the Vietnam War. Hope had performed USO shows for nearly half a century. So it came as no surprise to anyone when he toured Vietnam. But he quickly polarized his military audience after espousing his friend Richard Nixon’s ‘foolproof’ plan to come out of the war victorious.

The soldiers responded to his tone-deaf assessment by booing him. He lost even more of his younger fans when he came back to the states and proceeded to serve as Nixon’s mouthpiece.

An 8th and final ‘Road to’ film planned shortly after Hope’s cringe-worthy sexist comments at the Miss World Pageant. And his Vietnam gaffe certainly didn’t make things easier for him either. ‘Road to the Fountain of Youth’ as it was going to be called already had a script and a producer lined up by 1977. The film never ended up making it to production though because Crosby died of a heart attack before it could make it to that phase. He was laid to rest later that same year.

Crosby Wasn’t Without Blame Either 

Oh and as far as Crosby goes, you might have noticed his unmistakable absence in this discussion of Hope’s misdeeds. That’s not because he was some kind of blameless saint who just so happened to have an unfortunately problematic business partner. No, it’s because Crosby’s own laundry list of scandals and controversies weren’t revealed until 1983. It is when his son Gary published the tell-all memoir ‘Going My Own Way’.

That book made the claim that Bing was an emotionally and physically abusive monster. Who slapped insulting names on his kids like ‘Satchel Ass’ and ‘Bucket Butt’. Gary admits that he had a unique physique when he was a child. And that used to ‘annoy the hell’ of his dad who would beat him senselessly using whatever he could find – from belts to canes to planks.

Bing used to scheme up all the ‘fun new ways’ that he could think of to humiliate his boys for forgetting to do their chores. If one of them so much as left their underwear on the floor. They’d have to wear it around their neck for the remainder of the evening. Bing even coined his own term to describe this de-humanizing punishment – The Crosby Lavalier.

Gary’s siblings had very different reactions to their brother’s book. But even the volumes most outspoken critic, Phillip, confirmed that his father routinely used corporal punishment to keep his children in line.

Crosby Also Got Around More Than He Should Have 

But you know what else Crosby believed in? Yup, you guessed it, just like his buddy Bob Hope, Bing had a penchant for infidelity. He openly slept around and everyone in his orbit seemed to encourage that kind of behavior. Crosby’s friends would even gossip openly about his affairs with little regard of the fact that his kids could overhear everything that they were talking about.

After his death, Crosby’s legacy began to crumble pretty rapidly. But Hope was still alive and kicking and seemed pretty content to continue swinging his metaphorical sledgehammer around. In the 80s, he pumped the gas on his homophobic rhetoric by making an insensitive AIDS joke about the Statue of Liberty. Later on, he dropped a wildly offensive gay slur while he was a guest on The Tonight Show.

GlAAD did eventually receive an apology from him for that latter incident but by that time. Hope had already thoroughly established himself as an aging, crotchety, out-of-touch bigot. Not that that really mattered all that much to his most devoted fans. Hope was still given his own gallery at the Library of Congress just a couple of years later.

Hope lived long past his barbarous buddy Bing Crosby. He passed away on July 27, 2003, at the ripe old age of 100. But before he died, he admitted that he was ‘no angel’ and that in his life he has known ‘very few angels’, So at least he wasn’t completely out of touch with reality.

Well, here we are once again at the end of another facts-packed video. Hopefully, you’ve enjoyed going on this little joinery through the sands of time with us.

At this point, it’s probably abundantly clear that Bob Hope and Bing Crosby weren’t the light-hearted, slap-sticky, comedy duo that they appeared to be on screen. They were deeply troubled men who held some views that would get themselves run out of Hollywood by an angry mob with pitchforks in today’s socio-political environment. They very clearly represented the end of an era. What was once considered normal and even acceptable behavior in the entertainment industry. And quickly became a thing of the past but some aging stars who were clearly past their prime stubbornly held on to the old ways instead of adapting to the changing tides of society. 

That’s the real legacy that Bob Hope and Bing Crosby left behind. Sure they made some impressive accomplishments in their heyday. But they should have evolved if they wanted to hold on to their fame and keep their names untarnished.

Anyway, now’s you turn to let your voice be heard. Which half of this comedy duo did you find to be the wittiest, Hope or Crosby? Let us know in the comments section below.

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Written by Alex Carson

Alex Carson is a seasoned writer and cultural historian with a passion for the vibrant and transformative decades of the 1960s and 1970s. With a background in journalism and a deep love for music, film, and politics, Alex brings a unique perspective to the ever-evolving landscape of entertainment.

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