The King Of Cool's Dark History

1. He Came From Humble Beginnings

Dino wasn't a nickname. Dean Martin was born Dino Paul Crocetti on June 7, 1917, in Steubenville, Ohio. His father was an immigrant, recently arrived from a small commune in the south of Italy. His mother's origins are more mysterious, but she was likely from a similar region. Pops worked as a barber, and the working-class parents instilled a sense of Italian pride in their son.

But while he had a loving home life, Martin faced torment at school.

2. His School Years Were Miserable

Dean Martin didn't actually speak English until he was five years old. Before that, it was all Italian, all the time. He eventually enrolled in Steubenville's Grant Elementary, where he had to face the cruelty of other kids his age. He was the only one who spoke broken English, and his classmates pestered him ceaselessly about it.

School turned out to be completely miserable for young Martin. Maybe that's why he didn't stick around too long.

3. He Didn't Finish

School just wasn't it for Dean Martin. He made it to the 10th grade before finally dropping out for good. He'd overcome his strong Italian accent and won over the bullies, but he still thought education was a complete waste of time. It didn't help that he thought he was smarter than all of his teachers. Just like that, the teenaged Martin set out in the world to try and make a name for himself.

But he didn't end up in the spotlight right away. He had to tread a dark path first.

4. He Found An Illicit Career

Martin tried out the working-class life like his father, landing a job in a steel mill—but can you picture Dean Martin working in a steel mill? He quickly moved on to other gigs. They just happened to be on the wrong side of the law. He bootlegged liquor for a time (Prohibition was a heyday for ambitious, uneducated young men like Martin), which put him into contact with some shady characters.

It also landed him his most dangerous job yet.

5. He Knew How To Use His Fists

All throughout school, Dean Martin had to defend himself from bullies who singled him out for the way he talked. It must have been a nightmare—but at least it taught him how to defend himself. Right around the time he dropped out of school, he started prizefighting under the name Kid Crochet. The career choice bought him a broken nose, a torn-up lip, and shattered knuckles (he couldn't afford the tape boxers usually used to wrap their hands).

But fighting in the ring was one thing—he soon found an even more brutal way to make a quick buck.

6. He Needed Money

Dean Martin struck out on his own while young and moved into an NYC apartment with another young Italian man named Sonny King. Both of them dreamed of a life in show business (King later became a lounge singer and unofficial Rat Pack member), but for now, they were just two young punks who needed rent money.

They had limited skills, but both of them could take a punch. So they came up with an idea...

7. He Made It The Hard Way

Roommates Martin and King ran a secret fight club out of their apartment. They'd charge New Yorkers to come and watch them bare-knuckle box—and they made sure to put on a show. Each night, they fought until one of them knocked the other out. I have to imagine there were easier ways to make a quick buck, but fighting was all Dean Martin knew at that point.

After a while, he realized getting beaten up for a measly sum every night probably wasn't the best career choice. But he wasn't ready to go on the straight and narrow just yet.

8. He Found Where He Belonged

After boxing, Martin landed a gig working in an illicit speakeasy/casino behind a smoke shop. He worked roulette tables, dealt cards, and entertained the guests. Now that sounds a little more like the Dean Martin we know! The shady lounges of speakeasies showed this tough Italian-American teenager a new world—and he liked it.

It was time for the tough guy to take the stage.

9. He Hit The Stage

Dean Martin was used to putting on a show, and he quickly learned that singing was a lot more fun than getting punched in the face. He started singing at whatever clubs he could, legal or not. He started off mimicking other crooners like Perry Como, and the people liked it. Soon, he sang with a popular local band, earning steady paychecks and making a name for himself.

The only problem was, he was making the wrong name...

10. He Needed A New Name

The world didn't yet know Dean Martin. They barely even knew Dino Crocetti. The crooner started going by Dino Martini, but the same anti-Italian sentiment that ruined school for him once again reared its ugly head. Sadly, the name Dino Martini was holding him back—and bandleader Sammy Watkins knew it.

Watkins told young Dino he should go by Dean Martin, and the rest is history. He was ready to shoot to stardom. Unfortunately, that came with some serious complications in his personal life.

11. He Got Hitched

Martin married for the first time at 24 years old. Her name was Betty McDonald, and she married Dino Crocetti, the young and upcoming lounge singer. The pair of them had four children together, but this was no fairy tale marriage. As Dino Crocetti became Dean Martin, their relationship started to tear at the seams.

It only got worse when a new face hit the scene.

12. He Met Someone Who Changed His Life

In the mid-1940s, Dean Martin found himself in the same lineup as a boisterous young comic at New York's Glass Hat Club. The kid's name was Jerry Lewis, and right away Martin could tell there was something special about him. Neither of them knew it at the time, but this was the start of a beautiful friendship—and a terrible feud.

13. Their First Show Went Horribly

The pair decided to work together, and they debuted Martin and Lewis in Atlantic City in 1946. It was the birth of one of the greatest duos show business had ever seen. It was also a total, unmitigated disaster.

14. They Had To Think Facts

Whatever Martin and Lewis prepared, the crowd wasn't having it. The pair bombed so hard that the club's owner told them they had to come up with a better act before their second show of the night or he'd fire them. That's how Dean Martin and Jerry Lewis ended up huddling in a dark alley behind the club, frantically trying to think up anything that could save them.

Eventually, they both just said, "Screw it," and went for broke.

15. They Struck Gold

It's not like Martin and Lewis could just write an entire act before their second show. So instead, they just threw everything they had at the audience. Martin sang songs, Lewis performed skits, and the pair of them ad-libbed banter throughout. Now, if these were two normal performers, that sounds like a complete train wreck.

But this was Dean Martin and Jerry Lewis. The crowd went nuts—and the duo never looked back.

16. They Made It To The Copa

This complete Hail Mary quickly transformed into a successful act that sent Martin and Lewis all over the Eastern seaboard. They eventually brought their act to New York's legendary Copacabana. This was no small-time club; they'd reached the big time. After the Copa, there was only one place to go next. It was about time the whole world discovered Dean Martin.

17. They Hired A Legend

Martin and Louis made their TV debut in 1948 on The Ed Sullivan Show, to a rapturous reception. They were both ready to take their act out of nightclubs and into TV and film, so they hired a pair of young comedy writers to craft material with them. One of those young writers happened to be Norman Lear, who'd go on to create some of the most popular shows in television history.

But while Dean Martin's career was rising, his marriage was going up in flames.

18. His Wife Didn't Like The New Him

It seems that Betty McDonald preferred the struggling Dino Crocetti to the successful Dean Martin. The paid divorced in 1949, with Martin gaining full custody of their four children. McDonald, it seems, wasn't cut out for the spotlight; she lived out the rest of her days in obscurity in San Francisco. Meanwhile, Dean Martin's star continued to rise—and he wasted no time finding a new woman to share his bed.

19. He Moved On Really Fast

Though Martin and McDonald divorced in 1949, their marriage was probably over long before that. By the time they split, he was ready to move on again—and that he did. He married Jeanne Biegger, a former Orange Bowl Queen, mere months after his divorce from McDonald. Jeanne proved to be Martin's longest love, and they remained married for nearly 25 years, though it wasn't all wedded bliss.

For now, Martin had his career to focus on—and he was about to enter a whole new world.

20. He Made A Genius Deal

1949 was a busy year for Dean Martin. He got divorced, got married, and appeared in his first movie: My Friend Irma. Though he and Lewis earned just $75,000 between them for the film, that was peanuts compared to what was coming next. Their agent negotiated one of the best deals in Hollywood history, allowing them to produce one film a year, over which they'd have complete control.

They also had final say over all nightclub, radio, TV, and record appearances. That deal netted both Martin and Lewis millions. This dynamic duo was quickly on their way to conquering Hollywood—but this was when the cracks started to show.

21. He Resented His Partner

No one could deny the chemistry between Dean Martin and Jerry Lewis on stage—but when the curtain fell, it was a different story. While Lewis always got to be the funny man, Martin felt trapped by always playing the straight man. He wanted to mix up their formula, but both Lewis and their producing partner refused. Martin grew more and more bitter. The relationship grew tense and uncomfortable.

The camel's back was strained—but what would be the last piece of straw?

22. Critics Dragged Him

Dean Martin played second fiddle to nobody, but that was quickly becoming how people saw him. Critics heaped praise on Jerry Lewis and claimed that he was the real talent behind the duo, saying anyone could have played Martin's part in the team. Martin seethed, while Lewis basked in the adulation, unconcerned and unsympathetic.

Finally, while promoting their latest film, 1954's Living It Up, something happened that finally pushed Martin too far.

23. They Cut Him Out

Even Dean Martin grew jealous sometimes, and the critics weren't helping matters—but after the duo's 1954 photoshoot for Look magazine, he'd finally had enough. The pair of them posed for the promotional shoot, but when Martin saw the final cover, his blood ran cold. They'd completely cropped him out of the photo!

Martin was officially done with Lewis—except he still had one big problem.

24. They Wouldn't Speak to Each Other

Martin was completely ready to move on, but the pair still had to finish making their last movie together, Hollywood or Bust. Despite their playful attitude on screen, the set became excruciatingly awkward. Martin and Lewis both refused to speak to the other whenever the cameras weren't rolling. So, was Martin just being a baby, or was Lewis being a diva? Well, years later, Lewis would finally reveal the truth.

25. It Was Lewis's Fault

The Martin and Lewis feud has gone down in history, and fans all wanted to know one thing: Whose fault was it? Well, in his memoirs, Lewis placed the blame squarely on his own shoulders. The 50s saw him become one of the biggest stars in Hollywood, and all that success went straight to his head. His ego grew to the size of Texas, and he treated the people around him like dirt—Martin included.

That would at least explain the cruel words Martin spoke to him, ruining their relationship for good.

26. He Went For The Throat

Hollywood or Bust, while not particularly great on-screen, was even more of a nightmare behind the scenes. Martin was totally done with Lewis and barely even bothered to show up to work. His disinterest led to more and more vicious arguments with Lewis. Finally, Martin snapped. He looked his old partner in the eye and said, "To me, you're nothing but a ****ing dollar sign."

They somehow finished the movie, but the pair was finished too. They broke up for good in 1956, exactly 10 years after they first teamed up. Lewis likely assumed Martin would be lost without him. He never could have imagined what came next.

27. He Found A New Partner

Lucky for Dean Martin, Jerry Lewis wasn't his only friend in show business. He also happened to know another popular lounge singer, one whom he'd met back in the 40s when he was still struggling. Maybe you've heard of him: Frank Sinatra. Maybe Lewis thought Martin was finished after they split—little did he know, Martin was about to be bigger than ever.

28. He Joined The Rat Pack

From Martin and Lewis to the Rat Pack. With Sinatra and Martin at the center, this legendary group of performers included Sammy Davis Jr., Peter Lawford, Joey Bishop. Their charm, style, and banter made them legends—and they knew the perfect place to take their act: The City of Sin called to them, and they were ready to answer.

29. They Took Vegas By Storm

The Rat Pack just wouldn't be the same without Las Vegas. On any given night, you might see one, two, or all of them take the stage at one glamorous casino or another, depending on how they felt. Eventually, hotels like the Sands started putting, "DEAN MARTIN—MAYBE FRANK—MAYBE SAMMY" on their marquee. Without Jerry Lewis taking up the oxygen, Dean Martin thrived like never before.

Audiences adored his crooning, his banter, and his slapstick comedy alongside the other Rat Packers. But while America fell in love with the group, they were more scandalous than most of us realize.

30. He Pushed Boundaries

The Rat Pack reached their height in the 1960s, when America was changing. Despite their clean-cut appearance and charm, the group pushed boundaries in ways no one expected. Their jokes revolved around taboo themes like Martin's heavy drinking and Sinatra's constant womanizing. The group also delved into the world of politics, supporting the civil rights movement and refusing to perform at clubs that barred African-American or Jewish performers.

Martin and the rest risked it all to do what they wanted—and it paid off bigger than they could have imagined.

31. He Took Center Stage

Martin had made his name next to Jerry Lewis, and then next to the Rat Pack—so it was time for him to set out on his own. The Dean Martin Show began its 264-episode run in 1965. But Martin wasn't about to change just for network censors. He completely improvised every show, which often sent him down scandalous tangents. He also used Italian curse words constantly.

To most American viewers, it was just part of his charm—but speakers of the language were furious, sending a deluge of complaints NBC's way. The network tried its best to rein in the incorrigible Martin. They failed miserably. If anything, he got worse.

32. He Had A Ridiculous Contract

Despite the controversies, Martin was so popular he could continue doing whatever he wanted—and what he wanted to do was "less." When he renegotiated his contract, he included one of the strangest clauses in history: He didn't have to show up! Well, at least not for rehearsals. He improvised every show anyway, so he struck a deal that let him spend the whole week on the golf course, only showing up for tapings.

By this point, he had an infamous reputation as a drinker, and his antics only added fuel to the rumors—but audiences didn't know the truth about him.

33. His Act Was All A Lie

Dean Martin was America's most loveable drunk. From the glass of scotch that remained in his hand throughout all his performances to his vanity license plate "DRUNKY," everyone knew that Martin was the Rat Pack's boozehound. But, what people didn't realize was, it was all an act. Martin was actually probably the closest thing the Rat Pack had to a teetotaller.

The drink in his hand on stage was apple juice more often than not, and he was usually the first to call it quits at parties, preferring to spend time at home with his family. That didn't stop the rumor mill from churning, though.

34. He Was Too Good At It

Joe E. Lewis, a comedian from Martin's youth, taught him the loveable-drunk schtick, but the problem was, Martin was too good of an actor. He played the part in his act, but when he started playing drinkers on screen, people began to talk. He played an alcoholic so convincingly in movies like Some Came Running and Rio Bravo that the tabloids started writing about his not-so-secret "addiction."

They were completely wrong, of course, but Martin still took advantage of the rumor. He still had his fair share of quirks, though...

35. He Had A Crippling Fear

Whenever Martin checked into a hotel, he required them to give him a room on the first floor, no matter what. Most people probably assumed he was just a diva—but there was actually a darker reason for the request. Even into adulthood, Martin suffered from crippling claustrophobia, and more than anything, he hated stepping into an elevator. He once even walked up 18 flights of stairs rather than take one of the "coffins," as he called them.

Since Martin always kept a certain mystique around him, quirks like this started to give him a reputation. His crumbling marriage only made it worse.

36. He Had A Terrible Year

For decades, Dean Martin seemed on a constant upward trajectory. In 1972, however, he began to fall back to Earth. He filed for divorce from his wife of over 20 years. Just a week after that, the Riviera in Las Vegas canceled their contract with him because they thought he was too demanding. Now 55, Martin was in the midst of a full-blown mid-life crisis.

And what do men in mid-life crises do? They make terrible mistakes, of course!

37. He Got Married Ridiculously Quickly

Dean Martin was clearly a big wife guy. He'd married Jeanne less than a year after his first divorce, and this time around he wasted even less time. Less than a month after his 24-year marriage ended, he wed Catherine Hawn, the receptionist at a Beverly Hills hair salon. He was 55, and she was 26; a rebound from the most serious relationship of Martin's entire life.

Do you really think they got a happily ever after?

38. He Made A Series Of Bad Decisions

Unfortunately, the star-cross'd Martin and Hawn weren't so star-cross'd after all. They divorced less than three years after tying the knot. After that, Martin still hadn't learned his lesson. He proposed to Gail Renshaw, a beauty queen and former Miss World contestant. I guess he finally came to his senses, though, because they cut off the engagement before they could actually get married.

Clearly, Martin was having some trouble with the ladies—but just as his love life was crashing and burning, he was about to rekindle one of the most important relationships of his entire life.

39. He Stunned His Old Friend

Anyone who thought the Dean Martin/Jerry Lewis feud was just a brief tiff had another thing coming. After performing together for a decade, the pair hadn't spoken in private once in 20 years. So Frank Sinatra came up with a devious plan to change that. During a telethon for the Muscular Dystrophy Association, Sinatra utterly stunned Lewis by bringing Martin out on stage.

The pair hugged, the crowd went wild, and the money started pouring in—but not everyone was happy about the reunion.

40. Lewis Wasn't Thrilled

Sinatra did a good job completely keeping Lewis in the dark about the surprise—and not everyone likes surprises. Before Martin crossed the stage to embrace him, you can hear Lewis mutter, "You son of a ****..." to Sinatra under his breath. He eventually recovered from his shock, and while the duo never again became as close as they'd once been, they maintained a healthy friendship for the rest of Martin's life.

It was a happy moment, and one to remember—especially in light of the horrible tragedy that would eventually derail Dean Martin's entire life.

41. His Son Was A Golden Boy

Despite his on-stage persona, Dean Martin was a family man, first and foremost. He had eight children whom he loved and supported through all the ups and downs of his career. He named his first son with his second wife after himself, and young "Dino" Martin soon grew into the apple of his father's eye. The golden boy of the family, Dean Paul Martin took after his dad and then some.

He sang and acted, just like his pops. He also played professional tennis. As if that wasn't enough, he even became a fighter pilot and joined the California Air National Guard. Dino brought immeasurable joy into Martin's life—which made his terrible end all the more devastating.

42. His Boy Went Missing

On March 21, 1986, the 35-year-old Dean Paul Martin took part in a routine training mission over the California desert. During the exercise, Martin's plane disappeared from the radar over a particularly cloudy mountain range. Urgent calls were sent out over the radio, and yet no response was forthcoming. The son of one of America's most popular entertainers was missing, and the search was on.

43. He Started Falling Apart

Search helicopters and planes spent several tense days scouring the mountains for any sign of Dino's plane, yet came up with nothing. Ronald Reagan, then President but also a longtime friend of Martin's, even sent the nation's most advanced spy plane to join in the search. Meanwhile, Martin sat at home, frantically burning through one smoke after another, praying for the news that the search parties had found his son alive.

His worst nightmare had come to life—and he felt a pain that his close friend, Frank Sinatra, knew all too well.

44. His Friend Knew His Pain

It must have been nearly impossible for anyone to know what Martin was going through, but if someone did, it was Sinatra. A decade earlier, his mother had lost her life in a plane crash—eerily in the exact same area where Dino's plane had disappeared. Sinatra remained by Martin's side as they anxiously waited for news. Martin's daughter recalled Sinatra, voice shaking, saying, "If there's anything I can do, pal. Anything at all..."

But despite his shared grief, there wasn't anything he could do. All they could do was wait for the phone to ring. When it finally did, Martin got the news he'd been fearing this whole time.

45. He Was Willing To Try Anything

Martin was willing to do anything to find his son. He even hired two psychics to help in the search. One touched Dino's flight suit and recoiled, saying that he was dead. The other pointed them towards San Gorgonio Mountain—the very same peak where Sinatra's mother had met her fate. Three days after the plane went down, the search party approached the mountain and found what they had been looking for.

Dean Paul Martin's aircraft lay demolished on the mountainside. There were no survivors. The news devastated Martin, obviously. Still, no one could have imagined the dark spiral it sent him down.

46. His Friend Tried To Help

Anyone close to Martin could tell that he just wasn't the same man after his son passed. He was depressed, demoralized, and defeated. His longtime friend Sinatra, still seeking any way to help him, dragged him along on a massive stadium tour, hoping to take his mind off his grief. Unfortunately, his plan backfired horribly.

47. He Went On A Disastrous Tour

Sinatra had the best intentions, but his way of "helping" just made things worse. He thought the adoring crowds and late-night parties would shake Martin out of his stupor, but they had the opposite effect. Martin vastly preferred smaller, nightclub audiences, and the sea of faces in large stadiums made him miserable. He also butt heads with Sinatra almost every night.

Old Blue Eyes still wanted to party until dawn as they had in the 60s, but Martin was old, tired, and depressed. The entire tour was miserable—and that's when the public saw a side of Martin that they'd never seen before.

48. His Performances Were Disturbing

Dean Martin had spent decades cultivating a persona as a loveable boozehound—well, on this infamous tour, he dropped the loveable part. His behavior stunned the crowds who showed up to see their beloved Dino. He forgot the lyrics to his songs, stumbled through his lines, and apparently once even flicked a lit smoke into the audience in disgust.

You don't have to be a genius to tell that this wasn't going to last.

49. He Didn't Last

The tour had barely begun and Martin was already at his breaking point. After a show in New York City, the Pack returned to their hotel. Frank was ready to party, so he dragged his aging friends out of bed and down to the bar. Or at least, he tried to. Sammy Davis Jr. joined him, but Martin had had enough. Sinatra begged him to come downstairs, but Martin gave a flat, "No," and slammed the door.

Later that same night, Martin got on his private jet and flew back to LA. He'd had enough.

50. He Had Changed

Sinatra's grand plan to cheer Martin up failed spectacularly. After just a handful of miserable shows, Martin abruptly quit and went home, leaving his friends to continue the tour without him. This sort of behavior was completely unlike the King of Cool America had come to love, but as we said, his son's passing changed him forever.

Believe it or not, crooning with Sintara like the old days wasn't going to solve his woes. At least he found some solace in his remaining family.

51. His Family Kept Growing

Losing Dino hurt unbearably, but Martin still had seven other children whom he adored—and now that they were growing up, his family grew with them. He gained several famous sons- and daughters-in-law, including the Beach Boys' Carl Wilson, actress Olivia Hussey, and even Lou Costello's daughter Carole.

After his son's passing, Martin put his career on the back burner and spent as much time as possible with his growing family—unfortunately, he didn't have that much time left.

52. His Received A Terrible Diagnosis

Martin may have walked the stage with apple juice in his glass, but the smokes were real. In September 1993, doctors at Cedars Sinai diagnosed him with lung cancer. They told him that he needed surgery immediately to prolong his life. Martin's response was tragic. Maybe the man he was before losing his son would have said yes, but that man was gone.

To his family's dismay, Martin refused the surgery and resigned himself to his painful fate—which wasn't that far off.

53. He Ran Out Of Time

Martin retired from public appearances at the start of 1995 and spent his final year with family and friends. He succumbed to acute respiratory failure at his Beverly Hills home on Christmas Day, 1995. In a strange coincidence, he gave his last breath 29 years—almost to the second—after his mother had passed. He was 78.

Dean Martin, the King of Cool, would never croon again.

54. The Strip Dimmed For Him

Not much can dim the bright lights of the Las Vegas Strip, but the passing of Dean Martin did it. The casinos where he'd tread the stage for so many years all brought their lights low in his honor, a fitting tribute to the King of Cool.

55. He Had Shady Fans

When he became a singer, Dean Martin left his shady past as a bootlegger and bare-knuckle boxer behind—but that life still stalked him at every turn. His pal Frank Sinatra had mob connections all across the country, and the Rat Pack often performed for these kinds of disreputables. Though the gangsters intimidated most of the Rat Pack, Martin was a different breed.

He'd been on the wrong side of the law before, and he knew how to hold his own.

56. He Stood Up To The Mob

Martin hated the mob shows they performed, and he didn't try to hide it. After one show, a group of wiseguys approached him and said, "We want to thank you for helping us out." Most performers would be intimidated, but not Martin. He looked them square in the eye, pointed to Sinatra, and declared, "No, I did it for Frank," then stalked off.

After the illicit activities of his youth, it seemed like Dean Martin had left that life behind for good—or maybe he was just hiding something.

57. A Shocking Secret About Him Came Out

One of the most infamous mobsters with whom the Rat Pack interacted was Meyer Lansky, and Lansky had a beautiful daughter, Sandra. Though Martin managed to maintain a squeaky-clean reputation throughout most of his life, years later, Sandra dropped a bombshell in her memoirs. She claimed to have had a passionate affair with longtime family-man Dean Martin.

The details that emerged were some of the most scandalous of Martin's entire life.

58. He Was A Machine

​In her memoir, Sandra Lansky wrote rapturously of Martin's, ahem, abilities. "I had never seen anything like Dean Martin’s masculinity. We made love six times in a night that wouldn’t stop. I counted." She clearly didn't hold anything back in this book. In fact, she went even further: "With me he wanted to be fully conscious and savor every moment. Between rounds of lust, we’d split a Coke."

But that's not even the most shocking part of Lansky's account. The timing makes it so much worse.

59. He Strayed From His Family

According to Lansky, her affair with Martin occurred while his wife was pregnant with/gave birth to their daughter Gina. Lansky claimed that the pair had an "unspoken pact" to never discuss their families when they were together, so she didn't learn about this until later.

60. He Has A Connection To The Manson Family

Dean Martin also has a surprising connection to one of the most chilling crimes in the history of Hollywood. Throughout the 1960s, Martin delighted audiences as the loveable secret agent Matt Helm. Martin starred in four Matt Helm movies, culminating in 1969's The Wrecking Crew alongside up-and-coming starlet Sharon Tate.

Not long after the film's release, Tate infamously became one of the Manson Family's victims on Cielo drive. The chilling slaying evidently shook Martin so deeply that he retired the Helm character for good.