It takes tons of hard work and a phenomenal sense of humor to land yourself on the “Funniest People of All Time” list. Only the perfect arsenal of jokes will hit the right “funny” nerve with a wide range of crowds. But for Bob Hope, it was all in a day’s work.

Hope cemented himself in the pantheon of stellar comedians the world will never forget. He was beloved by audiences everywhere, especially troops overseas, but the man who set the stage ablaze wherever he went was much more complex than we thought.

1. There’s a reason the Guinness Book of World Records dubbed Bob Hope the “most honored entertainer in the world”: Over his career, he received over 2,000 awards, including 54 honorary doctorates.

HFPA Archives

2. To name a few others, he received the Congressional Gold Medal, Presidential Medal of Freedom, the Air Force Order of the Sword, Most Excellent Order of the British Empire, and the Pontifical Equestrian Order of St. Gregory the Great.

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3. Even though Hope was celebrated by Americans and didn’t have an accent, he wasn’t actually from the United States! He was born in a county in London called Well Hall in 1903.

Library of Congress

4. It was at the age of five when Hope and his family moved to Cleveland, Ohio, where they lived for many more years. They even had to pass through Ellis Island before finally settling down.

5. Hope always knew the value of things around him and never took anything for granted. Long before fame hit, he actually sold two-cent newspapers when he was young to earn an extra buck. His parents instilled this work ethic.

6. Many entertainers got their interest in the stage from their parents. Hope’s father worked as a stonemason, but his mother did some light opera singing. So, entertainment was in his blood.

7. Even though getting a solid education is super important, Hope didn’t get too far in school. It seems like someone with such accolades would have made it through at least high school, but Hope dropped out!

CBS

8. Like many celebs, once Hope got famous he took on a pseudonym as opposed to using his actual name. He wasn’t born Bob; his parents named him Leslie Townes.

Wikipedia

9. In 1928, Hope had his first solo act at Chicago’s Stratford Theatre. He went by “Bob” because he felt it sounded “chummier.” After his stint at the theater, he toured Midwestern cities performing in vaudeville shows.

10. When Hope met actor and singer Bing Crosby in 1932, the two became best buds. They clicked over their similar personalities and acting styles, and they went on to perform song and dance routines together in films.

Wikipedia

11. Hope and The Brady Bunch are connected. A struggling college student named Sherwood Schwartz landed a gig to write jokes for Hope part time. This tiny gig resulted in massive success.

12. Schwartz eventually went on to create The Brady Bunch and Gilligan’s Island. Even late in life, Schwartz described his rise to fame in Hollywood as a total accident, and he had Hope to thank for everything.

13. The Ukrainian comedian Yakov Smirnoff made a career off of the “Russian Reversal” series of bits like, “In Soviet Russia, TV watches YOU!” During the 30th Academy Awards in 1958, Hope was the first to drop this punchline.

14. Bob Hope may never have had a career in professional sports, but he was linked to the famous Harlem Globetrotters. He was named an honorary member of the team, along with a few other celebs.

15. When fame starts to ramp up, it can be tough to stay loyal to a spouse when a lot of people begin taking interest in you suddenly. However, Hope was dedicated to one woman his whole life: Dolores Reade.

16. War is a tough time for everyone involved, especially those who fight on the front lines to protect our freedom. Hope knew how difficult it was and took plenty of trips overseas to visit troops.

17. The troops quickly grew to adore Hope. He was a beacon of positivity and humor during such troubling times, and performing never seemed like work for him. Bob was more than happy to put smiles on soldiers’ faces.

18. It’s one thing to be awarded medals for going above and beyond the call of duty, but man, Hope had so many medals you needed more than one hand to count them!

Library of Congress

19. In 1997, the United States Congress wanted to recognize all of the of work Hope did for America and the troops overseas. So, Congress named him an “Honorary Veteran.”

Wikipedia

20. Hope was so beloved by the military that he actually has a setup inside Kettering Hall at the National Museum of the United States Air Force. Visitors can watch footage of the man in action.

21. Amazingly, Hope met Tiger Woods when the golfer was only two years old! The toddler was featured on an episode of The Mike Douglas Show in 1978 and had a putting competition against Hope.

As a standout in the world of comedy and entertainment, Bob Hope made friends across the entire industry. He appeared on the very first episode of fellow comedian Jerry Lewis’s talk show. The two had a lot to talk about.

1. During a 1965 performance in Las Vegas, Jerry Lewis took a severe tumble off a piano while doing his routine. It was so bad he almost suffered permanent paralyzation. Luckily, he made a full recovery.

2. Even though Lewis recovered from the piano fall, the recovery led to a brutal addiction to painkillers. For 13 years he lived in the dark depths of opioid addiction but finally kicked it in 1978.

3. As much as Lewis did for comedy, he also did a lot for filmmaking. He invented a “video-assist” feature that allowed for footage review immediately after filming. This saved so much money and time on editing.

4. As much as Lewis loved comedy, he also had one hobby he was obsessed with: He would cut and edit other people’s home movies for his own personal use. Then, if they wanted to watch, they saw his edited version.

The Delicate Delinquent

5. From an early age, Lewis took an interest in the theater. In fact, his father was a vaudeville entertainer who performed constantly, and his mother played the piano for a local radio station.

6. At the ripe young age of five, Lewis began performing on stage in New York’s Catskill Mountains with his parents. This was the same place where legends like Jerry Stiller and Lenny Bruce got their start.

Everett Collection

7. Lewis’ parents had such hectic schedules as entertainers they frequently left their son home alone while they performed gigs. This lonely time was likely where Lewis developed his need for attention, which turned into his desire to perform for audiences.

8. Like a lot of famous funny faces, Lewis spent a chunk of time as a child puling pranks on friends. Even as a teenager, he would break into homes and steal things like pies out of refrigerators.

Paramount Pictures

9. The name Jerry Lewis was just a stage name he went by. However, there’s a lot of mystery surrounding his actual name. His autobiography revealed his name was Joseph Levitch, but other documents claim it’s Jerome Levitch. Interesting…

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10. Even though so many people loved Lewis throughout his career, his son Gary told a much different story. He referred to his father as “a mean and evil person.”

11. As beloved an entertainer as Lewis was, his romantic life was tarnished by serial infidelity. He frequently cheated on his wives, and he would even openly brag about the affairs onstage without shame.

Wikimedia Commons

12. In 2009, Inside Edition explored a rumor Lewis had an illegitimate child with a model named Lynn Dixon. After discovering he likely was the father, Lewis ordered her to never contact him.

13. Everyone has their own quirks, and Lewis definitely had some odd ones. One thing he required his personal aides to do was arrange the bills in his wallet based on serial numbers.

14. One thing Lewis treated himself to once he hit mega-stardom was new socks. The guy literally wore a new pair of socks every single day because he loved the way the new material felt on his feet.

15. At just 15 years old, Lewis developed an act now considered one of his most famous. It was called “Record Act,” and it basically involved him lip-syncing a song and totally over-exaggerating the dance moves.

16. For 44 years in a row, Lewis hosted his ultra-popular Labor Day Telethon. The telethon raised money for the Muscular Dystrophy Association, which he was a national chairman for. So far, the telethon’s raised over $2 billion!

17. Even though Lewis graced plenty of stages, he always wanted to appear on Broadway. He finally got his chance in 1995 to fill in for a role in Damn Yankees. Whew, at last!

18. The Eddie Murphy film The Nutty Professor was actually a remake of the famous Lewis movie of the same name. Plus, Lewis himself was actually one of the executive producers!

Paramount Pictures

19. Everyone knew Lewis as a world-renowned funnyman, but he flipped the script for a Martin Scorsese film called King of Comedy in 1983. Critics and audiences were floored by the comedian’s serious side.

Embassy International Pictures

20. A lot of comedians are one half of a famous duo, and Lewis was no different; his celebrity partner-in-crime was Dean Martin. The two men were just getting their start when they first met and lept into stardom together.

Hal Wallis Productions

Dean Martin was known as the “king of cool,” and it’s easy to see why: His crooning, relaxed nature made him a popular performer on the stage and on the screen. It was his effortlessly cool personality that catapulted him to fame…

And it also resulted in salacious rumors about the Rat Pack. It may sound silly now, but these suave swingers were considered the manliest men in show business. They epitomized a slick kind of appeal that women apparently went nuts for.

Imagine growing up with these kinds of rumors swirling around your own father — this is exactly what Deana Martin went through as a young girl. Though the Rat Pack was once envied by all, Deana isn’t sure they’d be as admired today.  

When asked if the Rat Pack would have avoided controversy in the #MeToo movement, Deana didn’t skip a beat. “I think they would have only because they were so cute at it…” she started to say, but then she stopped, seemingly unable to answer.

VOAMusic

“He’s just being cute” is a common defense for harassment, in and out of Hollywood. This once-tolerated “cuteness” really doesn’t fly any longer, and with this in mind, Deana re-thought her answer to the question. 

After all, allegations of sexual harassment coming from this “glamorous” lifestyle is nothing new. The Friars Club — the exclusive, male-dominated club made famous by the Rat Pack and more recently by Harvey Weinstein — is, for example, no stranger to controversy.

Everett Collection

Deana Martin knew this, but she also knew how important the Friars Club was to her family. The reason she was talking about Dean and the #MeToo movement at all was because she was honored by the Friars Club in 2018… 

Stephen Sorokoff

And so, Deana Martin decided to answer honestly. “Well, now that I’m thinking about it, I don’t know if they would have survived,” she admitted. But when it came to her father’s drinking, smoking, and philandering ways, Deana was adamant about one thing.

The Dean Martin Show put the swinger in a less-than-flattering light, at least by today’s standards: Dean was the overly-tanned, slurring star of the show. He always held an Old-Fashioned glass, and if he flubbed a line from a cue-card, he never re-taped.

Despite his drunken demeanor, Dean was a huge success — but decades later, his daughter claimed that everything the public knew and loved about Dean wasn’t as real as anyone thought. Everything was, according to Deana, an act.

“The cigarettes, the womanizing, that was his shtick,” Deana said. In fact, it’s believed that the glass he held was actually filled with apple juice. She claimed that Dean was “go with the flow,” but would that fly today?

She thought that her father’s likability would have protected him during #MeToo, but she wasn’t totally sure. “I don’t really know [how he would be received] these days,” she admitted. But a different Rat Packer isn’t such a question mark.

“Frank…would have gone on with what he wanted to do,” she said of Frank Sinatra. Dean, on the other hand, wouldn’t “stay up with Uncle Frank and Uncle Sammy.” He was more of a family man than anyone knew…

Some Rat Pack members even spoke out against the rumors surrounding the group of playboys. “I never saw Frank, Dean Martin, [or] Sammy…drunk during performances,” Joey Bishop, a Rat Pack member, once revealed, along with other surprising claims. 

According to the comedian, the group’s drunken, womanizing reputation was “only a gag! And do you believe these guys had to chase broads? They had to chase ‘em away!” Joey claimed. As Deana said, maybe it was all truly an act…

“Dad was so handsome, so debonair,” Deana explained. “Every man wanted to be him, and every woman wanted to be with him.” Even with this reputation, Deana emphasized how “he was so different from what everybody thought he was.” 

And when it comes to whether or not the legendary group would survive in the #MeToo movement, Deana would rather look towards the future — especially towards her own version of her father’s famous celebrity roasts.

“I’ve been to these Friars Club roasts and [it gets] pretty vulgar,” she admitted. “For the Deana Martin Celebrity roasts…they’re not…racist, or anything like that,” she said. For Deana, being inducted into the Friars Club wasn’t something to be ashamed of…

Carol LoRicco

 “We could be the Cat Pack!” she said of her joining Liza Minnelli, Barbra Streisand, Dionne Warwick, and Kristin Chenoweth as the only women inducted. With or without his old fashioned, we think Dean Martin would have been proud of his record-breaking daughter!

While Dean’s life was filled with controversy in hindsight, another rat pack member stirred up trouble nearly every day. But Sammy Davis Jr. was born a world away from the glitz and glamour of Las Vegas. His life actually began Harlem, New York.

Davis’ dad was a singer and his mom was a tap dancer, so young Sammy had show biz in his blood. Before long, he was performing with the rest of his family.

In 1943, however, Davis Jr. was almost forced to change careers. He was drafted into the the United States Army, where he served as an entertainment specialist, performing for his fellow soldiers.

After he was discharged from service, Davis Jr. returned to the performance circuit. He rejoined his family dance troupe and recorded a few songs under various pseudonyms. Something bigger was coming, though.

Sammy Davis Jr.

In 1959, Davis Jr.’s reputation as a performer had grown. He was so well regarded that he famously joined the Rat Pack, linking up with Frank Sinatra, Dean Martin, and several others.

Biography.com

The group’s shows became the stuff of Las Vegas legend. Tourists and high rollers alike would flock to the Sands Hotel, hoping to hear even a single song or witty retort from the iconic performers.

The Rat Pack was a hit with the ladies, too. But a couple of years earlier, one particular woman had already caught Sammy’s eye. Their relationship, however, would be anything but straight forward.

One night in 1957, Davis Jr. was at Chicago’s Chez Paree night club. When he looked up from his table, he spotted actress Kim Novak sitting nearby. He was immediately struck by her beauty.

At the time, Novak was at the peak of her career. She had just starred in Alfred Hitchcock’s Vertigo and, while she didn’t love her performance, critics thought it was excellent.

Later that evening, Davis Jr. and Novak met at an after-party. The pair quickly became inseparable. In fact, their interactions even caught the eyes of some local newspaper reporters.

Before long, they had made the gossip column. One reporter coyly wondered, “Which top female (K.N) is seriously dating which big-name entertainer (S.D)?” Everyone knew who the writer was alluding to.

Word got back to Harry Cohn, the head of Columbia Pictures. The demanding boss couldn’t believe what he was reading; he was outraged that Novak had made the news in such a manner.

Los Angeles Times

Cohn felt that he had created Novak’s image as a Hollywood star. If the actress was in an interracial relationship, he believed, she would throw away her career…and Paramount’s share of the profits.

He ordered Novak to stop seeing Sammy. In addition to his status as a studio executive, Cohn also had mob connections; he wasn’t a man who you could simply disobey.

But Novak and Davis Jr. did just that. The couple continued to see each other, even going to some near-comical lengths to keep their relationship alive in the face of serious consequences.

When the couple met at a friend’s beach house, for example, Novak would arrive normally. Davis Jr., however, would hide under a pile of blankets so the paparazzi couldn’t spot him.

Cohn grew increasingly frustrated with the couple, even dispatching body guards to keep Sammy away from Novak’s home. Nothing worked, though. Eventually, the executive decided to call in the heavy artillery.

One day, Sammy Davis Sr. received a phone call from the crime boss Micky Cohen. The mobster explained that he wanted one simple message delivered to Davis Jr. in Las Vegas.

If Davis Jr. didn’t marry an African-American woman within 48 hours, Cohen explained, there would be serious consequences. The mob was prepared to break his legs and take his one good eye. For once, the singer wasn’t laughing…

Sammy knew the jig was up, so he made a quick phone call to singer Loray White. The pair had briefly dated but, this time, Davis Jr. had a different proposal.

Los Angeles Times

Davis Jr. told White that he would pay her $10,000 to marry him and pretend to be his wife. After things had settled down, he explained, they would divorce and forget the whole thing had ever happened.

She agreed, and the couple promptly tied the knot at the Sands Hotel. The mob and Cohn were satisfied and, true to their word, Davis Jr. and White would separate soon after.

Smithsonian Magazine

At that point, both Novak and Davis Jr. moved on with their lives. The couple never forgot their time together, though, and managed to reunite for one final sentimental moment.

Biography.com

In 1990, Davis Jr. was dying of throat cancer when Novak visited him at the Cedars-Sinai Medical Center . After years apart, they were able to properly say goodbye to each other one last time.

Performing in the heart of Las Vegas had some perks for the Rat Pack — money, fame, love. The absolute insanity of the city, however, drew the wrong kind of people. Sinatra got wrapped up with them, too.

Hailed as one of the greatest entertainers of all time, Frank Sinatra was the kind of man every woman wanted and every man wanted to be (at least, that’s what they say). But behind his sharp style and million-dollar smile, some believed “Ol’ Blue Eyes” was actually more dangerous than he led on.

SoundHound Inc.

It all began in the 1940s when “Sinatramania” was running wild across America. Teenage girls flocked to the young crooner like moths to a flame, and in the midst of the hysteria, another group of individuals began following him just as closely: the FBI.

The Rake

In the bureau’s mind, the kind of influence Sinatra could exert over an audience was dangerous, comparable to the blind devotion that WWII had made them all too familiar with. But this was just paranoia — after all, how dangerous could a singer really be?

The FBI attempted to shake their suspicions about Sinatra, but shortly after he was declared ineligible for the draft, a rumor spread that Sinatra had allegedly paid a doctor $40,000 to deem him unfit to serve. The bureau couldn’t ignore the whispers.

But after looking further into the tip, the FBI ultimately found that the reason for Sinatra’s exemption – a punctured eardrum and “psychological issues” – was legitimate. Still, something about the singer just didn’t sit right with the agency.

All About History

From very early on in his career, Sinatra associated with some very unsavory individuals, namely high-ranking members of the Mafia. Though Sinatra fervently denied being a mobster himself, his friendships painted an entirely different picture of a man so beloved.

Sam Giancana, the notorious leader of the Chicago Outfit, was one of the singer’s closest friends, and it was Sinatra who supposedly introduced him to then-senator John F. Kennedy in a bid to secure union votes for his presidency. Sinatra then worked gigs at Giancana’s nightclubs as payment for such favors.

Sinatra also introduced Kennedy to Judith Campbell Exner, Giancana’s girlfriend, who allegedly became one of JFK’s mistresses. She allegedly served as a liaison between Kennedy and Giancana during the CIA’s alleged plot to have the Mafia assassinate Cuban president Fidel Castro.

Biography.com

But Sinatra’s mob ties didn’t end there. FBI records give accounts of gifts from Chicago gambling bosses Joseph and Charles Fischetti (below), and Sinatra even performed at an Atlantic City club on behalf of Philadelphia mobster Angelo Bruno. His own godfather, Willie Moretti, exerted pressure to get him out of a 1951 contract.

All the while, the FBI was keeping tabs on Sinatra’s every move, including his frequent rendezvous with Detroit mobsters Anthony and Vito Giacalone. The evidence they collected didn’t look great for the singer.

“It was like clockwork,” recalled retired FBI agent Sam Ruffino. “A few times a year, we’d trail the Giacalones to the airport to pick up Sinatra. They’d spend the weekend together socializing before and after his shows.”

“Almost every night, [the police] shut the place down,” Ruffino continued. “And he didn’t make any apologies for it. Those were his friends. The fact that they were known hoodlums and murderers didn’t matter to him. He didn’t care, he was going to hang around with who he wanted to hang around with.”

Only the FBI seemed to care, however, until word got out that he had attended the infamous Havana Conference in Cuba alongside the Fischettis and Lucky Luciano. Then, newspapers across the country printed headlines condemning the singer and his actions.

Classic Driver

Still, Sinatra was never charged with criminal behavior, though his mob ties weren’t the only thing the government perceived as a threat. The FBI’s file on Sinatra is filled with additional accounts of “suspicious activity,” most of which revolved around his political sympathies.

Sinatra was an outspoken supporter of liberal policies and publicly condemned systematic racism and discrimination. His close association with JFK was also viewed as suspicious, and some in Washington even accused Sinatra of having ties to Communism.

Indeed, Sinatra defended individuals accused of being Communist, especially those in Hollywood. He helped found the Committee for the First Amendment, a group that supported writers and directors who were blacklisted during the Red Scare.

But Sinatra’s file didn’t solely serve as a means to build a criminal case against him. The FBI also kept records of the threats of extortion, blackmail, and violence made against him and was integral in advising him after his son, Frank Sinatra Jr., was kidnapped in 1963.

All along, however, Sinatra knew the FBI was watching him, and in both 1979 and 1980, the singer received copies of his file through the Freedom of Information Act. Though nothing ever came of the file, it speaks volumes about the lengths the government was willing to go to put Sinatra behind bars.

“Sinatra’s FBI dossier reveals a dismaying situation,” historian Gerald Meyer wrote in 2002. “At no time does it contain anything that even hints at an activity disallowed by the Bill of Rights.”

Despite this fact, the FBI kept Sinatra’s file open for nearly five decades, closing it only upon his death in 1998. During this time, the bureau amassed a staggering 2,403 pages on every word he spoke and move he made.