Dane Cook’s Disappearance From The Spotlight Is Finally Explained And It’s Catching People Off Guard

Dane Cook

Throughout the early 2000s, few could mention their favorite stand-up comedians without bringing up Dane Cook. With his storytelling prowess and firecracker personality, Cook sold out arenas across the country and made himself a household name. Yet just as quickly as he rose to fame, the superstar comedian vanished from Hollywood without a trace. Now he’s finally revealed the reason he’s been M.I.A. all these years and the steps he’s taking now to make his way back to the top.

All-Time High

It was 2005 when Dane Cook received the greatest news of his career so far: his newest comedy album was flying off shelves. He’d cemented himself as one of the best to ever hold a microphone. Yet, he still felt uneasy about his future.

Photo by Joe Coomber/FilmMagic

Shy Kid

Born in Cambridge, Massachusetts and raised Arlington, Dane Cook wasn’t always the ball of chaotic energy his comedy has made him famous for being. In fact, Cook was quite shy and introverted as a kid, though at home he described himself as a “wild child.”

Dane Cook / Facebook

Coming Into His Own

It wasn’t until his junior year of high school when he began acting and doing stand-up that Cook finally came out of his shell. He studied graphic design in college, though deep down he always knew that comedy was path for him.

Dane Cook / Facebook

Committing To Comedy

He began performing stand-up professionally in the early ’90s, eventually moving to New York in 1994. After bouncing around comedy clubs for a few years, he packed his bags and headed for the bright lights and opportunities of Los Angeles.

Photo by AaronP/Bauer-Griffin/GC Images

Big Break

Cook’s big break came in 1998 when he was offered a spot on Comedy Central’s Premium Blend. Just two years later, he landed his first half-hour special and broke into the mainstream.

Comedy Central

Platinum Album

In 2003, Cook released his first platinum-selling album, Harmful If Swallowed, and followed up with 2005’s Retaliation. The latter went on to go double platinum and became the first comedy album in nearly three decades chart in Billboard’s top five.

Photo by Matthew Simmons/Getty Images

Selling Out Arenas

By the mid 2000s, Cook had established himself as the king of comedy. Selling out arenas — including two shows in a single night at Madison Square Garden — at an unprecedented pace, the comedian showed no signs of slowing down.

Radio City Music Hall/Facebook

Called Out

Yet around the turn of the decade, persistent rumors began to dog the megastar. Apparently, a number of comedians had accused him of ripping off their material for his sets.

Photo by Jason Merritt/FilmMagic

Too Similar

One of the most significant accusations came from Louis C.K., who claimed that a number of jokes off Retaliation were actually taken from his own 2001 album Live in Houston. Though Cook denied the claims, fans couldn’t help but notice the similarities between the two sets.

Photo by Jason Merritt/FilmMagic

Soured Reputation

This controversy eventually led C.K. to parody the situation with a skit featuring Cook on his comedy series Louie. C.K. went on to say that he believed the joke theft was unintentional, though by this point Cook’s reputation as a plagiarist was already an established fact.

3 Arts Entertainment

Losing His Parents

Cook then suffered another blow when both his mother and father passed away within a year of one another. The loss had a significant impact on his career, as he began performing less and less in order to grieve.

Photo by Alo Ceballos/FilmMagic

Financial Ruin

But the final nail in the coffin came in 2008 when Cook’s half brother and business manager Daryl McCauley was arrested on embezzlement charges. Apparently, McCauley and his wife had been siphoning millions from Cook, leaving the comedian in financial ruin.

Photo by Alet Pretorius/Foto24/Gallo Images – Pool /Getty Images

Stepping Back

In the wake of this downturn, Cook told The Washington Post in 2011 that he was stepping away from comedy. Instead, he hoped to direct his energy toward another of his creative passions.

Photo by Jeff Kravitz/FilmMagic

Turning Towards Hollywood

Starting with his film debut in 1999’s Flypaper, Cook had pursued a career on the screen alongside his one on the stage. He played the leading man in rom-coms such as Employee of the Month (2006) and Good Luck Chuck (2007) and even tried his hand at drama in 2007’s Mr. Brooks.

Element Films

Panned Performances

Unfortunately, whether they were comedies or dramas, Cook’s movies weren’t very good. The comedian’s performances were almost universally panned, and most of his films failed to recoup their budgets.

Lionsgate

Not Giving Up

Still, Cook wouldn’t relent on his acting dreams, and after lukewarm reception to his voice role in Disney’s Planes (2013), he took a shot at producing and starring in the sci-fi drama 400 Days (2015). Sadly, this, too, was a box-office flop.

New Artists Alliance

Things Are Looking Up

But in recent years, Cook found success in television with a series of guest roles. His appearance on Workaholics in 2016 was well-received, and his role in a 2017 episode of American Gods proved that maybe Cook could be a dramatic actor after all.

Mail Order Comedy 5th Year Productions

Back To Comedy

Cook has also returned to doing stand-up, albeit on a much smaller scale. His “Tell It Like It Is” tour, which marked his first full-scale tour since 2013, ran from February 2019 to November 2019 and was met with positive reviews.

Photo by Emma McIntyre/Getty Images for SBIFF

He Knew It Wouldn’t Last

Looking back on his career, Cook says he always knew that his superstardom wouldn’t last. “I knew that it was going to happen,” he revealed back in 2015. “I told my family a couple of years earlier. [I said,] ‘I’m about to get my a** whipped in the spanking machine, big time.'”

Photo by Jason Merritt/FilmMagic

Back On The Upswing

Yet even so, Cook believes that “the pendulum swings both ways” when it comes to success. At least for now, it appears that the former king of comedy’s personal life, if not his career, is back on the upswing. His relationship with 22-year-old fitness trainer Kelsi Taylor has been kicking up a lot of conversation.

Instagram/Dane Cook

Big Age Gap

A lot of people have raised their eyebrows at the unlikely couple, after all, Kelsi is 26 years Dane’s junior. But Hollywood does like to talk a lot of gossip. Cook and Taylor have actually been together for four years and seem to be going stronger than ever. Other areas of his life, however, continue to be a source of tension.

Kelsi Taylor / Instagram

It’s Just A Number

Although comedians thrive by cultivating their own unique brand of humor, there’s one comparison that’s haunted Cook for his entire career. Critics and fans alike can’t help noting the similarities between him and 80s-era standup artist Pauly Shore. And unfortunately, the likeness isn’t always a positive one…

Nate “Igor” Smith / Wikimedia Commons / CC-BY-SA-3.0

Complicated Past

The comedic character from films like Encino Man and Bio-Dome never fully turns off his trademark persona, but he doesn’t sugarcoat his past. In fact, he’s had a wild ride since the very beginning. He told the Chicago Tribune in 2011: “You know that video where the baby crawls across the highway, and for some reason, doesn’t get run over? That’s me and my life.”

Jeff Kravitz / Contributor

Family Business

People might wonder how a guy ends up maintaining a surfer-slang, party-boy character for 30 years running. Well, few have experienced what Shore has throughout his life. He was born in Hollywood with a stand-up comedian father and a mother who became comedy royalty, and Pauly and his siblings were along for the ride.

Jeff Kravitz / Contributor

The Comedy Store

Sammy and Mitzi Shore opened the Hollywood institution The Comedy Store when Pauly was just four years old, providing him a front-row seat to comedy’s greatest legends. Whatever your opinion of Shore’s own comedic stylings, there’s no doubt that he honed his skills by taking notes from the best. Even better, he got his hands dirty.

New York Times / Pauly Shore

First Job

Shore described the strange things he witnessed comics do to the New York Times: “He’d pour milk on his head, rub a grapefruit on his elbow, and smear chocolate pudding on his chest. My little jaw dropped. After a performance, he’d go out to the parking lot to clean up. My first job at the Comedy Store was hosing down Lenny Schultz.” For the Shores, comedy was inescapable and all encompassing.

Wiki Commons / Mike Dillon

No Separation

Pauly remembers how typical it was for stars like Robin Williams to show up unannounced at their house, dressed in his Mork and Mindy costume, to talk to his mother in her office. Early on, it was obvious that this was a profession that drew a specific kind of person.

Getty Images / Silver Screen Collection / Contributor

Den Mother

“Comedians are very sensitive,” Shore told the New York Times. “My mom knew that, and she was like the den mother to all of them. She knew how fragile Robin was, and they had this kindness for each other that was pretty special,” The lens through which Shore saw the comedic greats who passed through his mother’s club was tinged with admiration and understanding.

LA Times / Courtesy of The Comedy Store

Comedy was King

Few people have known the kind of environment Pauly Shore was raised in, one where being a comedian was the peak of creativity, bravery, and grit. Plus, there was the fact that his mother dedicated her life completely to her club and the comedians that she believed had that special spark. It caused conflicts.

Twitter / The Comedy Store

Mitzi’s First Love

“My mom was very loving — but her first love was always the Store and the comics,” Pauly said. From his words, it’s obvious he was shaped to think comedians weren’t just heroes, they were tied to the love and admiration of his mother. Naturally, that left an impression.

New York Times / Pauly Shore

Nightlife Childhood

Another part of being a child witness to the comedy culture was the instability. Pauly’s reality as a third-grader was being awoken on school nights by the booming laughter of his mother and her famous comic pals, wafting the smoke from their joints up to his bedroom. Still, Shore’s proximity to show business elites was too cool to deny.

Daily News / Courtesy of The Comedy Store

Pryor Connections

“When Richard showed up at the Store, it was like a wave went through the club: ‘Richard’s here, oh my God, Richard’s here.’ I’d go out to the parking lot and open the door of his car. He’d get out, say ‘Heeeeey little man!’ and shake my hand.” Shore told the New York Times. Paling around with Richard Pryor was the silver lining of his usual childhood, but there were drawbacks.

Getty Images / EVAN HURD PHOTOGRAPHY / Contributor

Working Hard

Despite his privileged position of having The Comedy Store as the family business, it was clear to Pauly that his mother wasn’t going to hand out opportunities. Mitzi Shore amassed an incredible wealth running her clubs, living the good life chauffeuring her family in limos. However, if her kids wanted something, they had to work for it.

Getty Images / Jim Steinfeldt / Contributor

No Favoritism

“When I got into high school, I wanted a 100-gallon saltwater fish tank. Mom said she wouldn’t buy it for me, but that I could work for it — she made me the short-order cook on weekends at the Westwood branch of the Comedy Store.” It was abundantly clear that Mitzi wouldn’t show her son favoritism just because he was her kid.

Instagram / Pauly Shore

Pauly’s Mission

Besides filling orders in the kitchen, Pauly was expected to make some more out-of-the-ordinary contributions to the family business. The club scene in Los Angeles was competitive and cutthroat, which meant making strategic moves to stay ahead. Sometimes it fell to Pauly to find out information.

Instagram / Pauly Shore

Stealing Secrets

One of Pauly’s high school classmates was the child of an owner of a competitive club — the Improv. The son of nightlife legend Budd Friedman was stuck in the same sort of showbiz upbringing as Pauly Shore, which marked him as a target. Shore poached the names of the comedians doing sets at the Improv and reported back to his mother. Mitzi Shore took betrayal very seriously.

Wiki Commons

Mitzi’s Wrath

Pauly knew which comedians his mother had on her banned list for the ultimate infraction of performing at rival clubs. She even felt scorned by comics who took spots on HBO’s Annual “Young Comedians Special” hosted by Rodney Dangerfield. Some comics were exiled because they pushed Mitzi too far.

Getty Images / Robert Knight / Contributor

Family Tensions

Controversial comic Sam Kinison was slapped with a ban after bringing a gun to The Comedy Store on a coke-fueled overreaction to a fight. Mitzi got angry with Pauly for hanging out with Kinison, but he assured her he did so for strategic reasons, “I said, ‘Mom, you don’t understand. I’m not hanging out with him for drugs — I’m hanging out with him because he’s a genius.’”

Getty Images / Jeff Kravitz / Contributor

Breaking Point

The fight between Mitzi and Pauly led to a breaking point. He went home, packed his things, and moved out the next day. That was the catalyst that made Pauly embrace and pursue the dream that simmered inside from the time he was a small child watching comics kill on stage — he started doing stand-up.

Instagram / Pauly Shore

Finding His Persona

On the stage, Pauly could use his weird and somewhat dark, and neglectful childhood to get the laughs and work through the pain. He used what he learned from growing up in The Comedy Store to define a one-of-a-kind character that he’s never really strayed too far from.

Getty Images / Michael S. Schwartz / Contributor

The Weasel

Most people don’t know there’s a separation between Pauly Shore and his alter ego “The Weasel.” Admittedly the lines are blurred, as Shore is every bit the stoner-surfer who remains categorically unruffled and communicates primarily through slang called dudespeak. His over-the-top characterization made him stand out and won an audience in the early ‘90s.

Getty Images / Jeff Kravitz / Contributor

MTV Hero

MTV hired Pauly Shore as a VJ in 1990, which categorically changed his life. His Weasel persona was deemed hilarious by legions of young fans, leading to his own show Totally Pauly. He was the perfect personality to host MTV spring break coverage and maintain the party-hardy fun-loving brand. It looked like he was set up for the comedy career he’d always dreamed of.

Getty Images / Jeff Kravitz / Contributor

Film Star

Then came Shore’s slew of films that showcased his Weasel identity. First was Encino Man, by far the most critically and financially successful, but he had others too, namely Bio-Dome and Son in Law. By the mid to late ‘90s, though, the tide rolled back on Pauly Shore’s opportunities.

Getty Images / Archive Photos / Stringer

Pauly Shore Is Dead

The schtick that once made him a star became the fodder for cruel jokes and rejection. Working through his career stalemate left Shore depressed and creatively drained. In 2003 he made a mockumentary film called Pauly Shore Is Dead that chronicled his fall from stardom, which was well-received, though not enough to revamp his career.

Getty Images / Frazer Harrison / Staff

Back to Stand-up

However, giving up was never the Shore way. He learned from his parents how to weather the storm of show business and turned back to his roots — performing stand-up. For a decade, Pauly traveled the country as a working comic, and in 2020, he made his move comeback in the form of the Netflix comedy Guest House.

Getty Images / Gary Miller / Contributor

Inheriting Mitzi’s Responsibilities

Shore explores new projects like impersonating political figure Stephen Miller and hosting his podcast Random Rants, but there’s an even larger priority he’s saddled with these days — managing The Comedy Store. Mitzi Shore bequeathed a role in the family business to each of her children in her will when she died in 2018. Pauly stepped into his mother’s enormous shoes and inherited all the headaches that can come with it.

Funny or Die

Difficulty Of Running The Comedy Store

The biggest difficulty Mitzi Shore faced in her tenure as The Comedy Store’s owner and overlord was the comedian’s strike in 1979. Pauly explained to The New York Times, “My mom never really forgave the comedians, but pretty soon the drugs were flowing, and people were partying again, and everybody seemed to forget about it.” The strike remains a dark mark on the club’s history, though back then, they were breaking new ground.

La Jolla Light / Corey Levitan

‘Tonight Show’ Moves

In April of 1972, Johnny Carson moved The Tonight Show from its original home in New York City’s Rockefeller across the country to Burbank, California. Coincidentally, comedian Sammy and his wife Mitzi Shore opened the Comedy Store that very same month. They were ready to welcome the flood of hopeful comics who followed Carson out West for the chance to make it big.

NY Times / Library of Congress / NY World Collection

Big Break

One night in 1973, after killing onstage at the Comedy Store, Freddie Prinze impressed the right people. He was called to perform on The Tonight Show and overnight, his career exploded. From then on, the comics at the Store knew it could only take one great set to make you a megastar.

Raised By TV Blog

Mitzi Takes Charge

That same year, Sammy and Mitzi divorced, and as part of the deal, she got the club. The transition to the Mitzi era marked one of the most important moments in comedy history. She had a vision for what the Comedy Store could be and got straight to work enacting her strategic plans.

Baltimore Sun / The Comedy Store

Queen Of Comedy

Mitzi’s vision wasn’t just about the business end of things either. She ate, slept, and breathed comedy. Every night she handwrote the show lineups, developing deep friendships with the comics she saw potential in. Her bluntness was legendary, but running the Comedy Store was her biggest passion and calling. She gave everything to the club, including taking big gambles to see it succeed.

NY Times / Pauly Shore

Major Overhaul

Mitzi reconfigured the layout of the room, keeping the Original Room and adding the Main Room to the club where the top talent would perform. She switched to table service, so waitresses would come to your seat and take your order — now with a 2 drink club minimum, which became the standard.

The Comedy Store

Eye For Talent

Betting on her vision, Mitzi poured over 50 grand into the project with high hopes for the return. Thankfully, her vision paid off. But the success of the Comedy Store wasn’t based on the nitty-gritty logistical reconfigurations. No, it was based on Mitzi’s ability to spot talent. Every comic that set foot on her stage had to pass a Mitzi audition.

The Comedy Store

Stand-up Mecca

By the late ’70s, the Comedy Store was the stand-up Mecca. It was a time when some of the greatest comedians in history were given Mitzi’s stamp approval to cut their teeth on stage. When David Letterman was ready to call it quits and move back to Indianapolis, Mitzi believed in his talent and convinced him to stay. She had a sixth sense for seeing potential.

Getty Images / Evan Hurd Photography / Contributor

Pressure To Perform

Talent scouts frequented the club searching for the next big star. It was all on the line when you walked on that stage. Besides getting the laughs, all your greatest dreams — a network sitcom, a Tonight Show spot, the role of a lifetime — all dangled in front of you. In order to catch them, all you had to do was kill.

Boston Globe / Borsari / HBO

Paid In Opportunities

To Mitzi, she was running a showcase. A chance on her stage was comedy college, training performers for what came next — their big breaks. It was an opportunity to step out on her Main Room stage, the most direct launchpad that a comic could find in LA. And that’s where the trouble started.

The Comedy Store

Not Compensating Performers

Mitzi could talk about the major opportunity of performing on her stage until the cows came home, but ultimately, customers filled the seats every night to be entertained by comics. The Comedy Store was raking in huge profits, and none of the performers were getting a cut.

Vulture / Showtime

Mitzi Won’t Budge

When people pressed Mitzi on the unfair policy, she stood her ground, claiming her club was akin to a college where you go to learn, not to make money. In fact, she doubled down saying the comics didn’t even deserve a measly $5 in gas money. The fallout was huge.

The Comedy Store

Comics Had Enough

The stand-ups were done standing for free. Comic Tom Dreesen, a former teamster, decided to do something about it. He proposed that they borrow some tactics from the labor unions and advocate for fair treatment. Acting as the mouthpiece, he went to Mitzi with a proposal.

Chicago Tribune / Terrence Antonio James

Dressen’s Proposal

Dreesen laid out the terms of his plan. The club had a $4.40 admission price, so he suggested that by bumping it up by $1, the extra income could be split amongst the comics who performed that night. In essence, Mitzi would still make the same profits as usual and the entertainers would walk away with something for their labor. It seemed fair, but not to Mitzi.

NPR / Showtime

Strike

The club owner refused the deal. With that answer, Dreesen employed the next part of the labor union strategy — the comics went on strike. The regular performers of the Comedy Store grabbed their signs and joined a picket line. Anyone looking to experience a fun night of laughs had to reckon with the biggest up-incomers in show business calling for change outside.

Calisphere / Los Angeles Public Library Photo Collection

The Demands

It wasn’t just one or two people. In total, 150 comedians stood to join the strike, refusing to cross the picket line. If Mitzi refused to come to an agreement and pay her comics, they wouldn’t budge. They called for the Comedy Store to close.

Calisphere / Los Angeles Public Library Photo Collection

Choosing Sides

News of the comedians’ strike was picked up by major news outlets, giving the Comedy Store some seriously bad publicity. Inside the club, the reaction was just as grim. The strike caused a schism between Mitzi and the comics. Everyone was forced to choose. The work of laughter became nearly impossible and Mitzi took it hardest of all.

The Comedy Store

Betrayal

The strike took a major toll on Mitzi. She felt betrayed by people she considered friends, people she had uplifted, believed in, and helped propel to success. It was the only time in her tenure that Mitzi considered selling the store. Thankfully, it didn’t come to that.

LA Times / Patrick Downs

Mitzi’s Allies

Not every comedian who worked the Store agreed with the strike strategy. One was furious enough to drive his car straight into the gathered mass of strikers, hitting and knocking down Jay Leno. Most of Mitzi’s supporters understood the love and dedication she had for her club and felt gratitude for the leg-up she’d provided. They wouldn’t disrespect her.

YouTube / SHOWTIME

Ultimate Tragedy

For six tension-filled weeks, the strike continued. Friendships were ruined, not just Mitzi’s, but between the divided base of performers. But the biggest tragedy of the Comedy Store strike was the death of a comedian who jumped off the 14-story hotel nearby, carrying a suicide note reading: “My name is Steve Lubetkin. I used to work at The Comedy Store.”

The Comedy Store

The Deal

Finally, in June of ’79, the strikers and Mitzi reached a deal. Performers in the Original room were paid $25 per set, and Main Roomer got 50% of the door fee. In truth, it took her three weeks of sitting with the terms to agree to them, as she’d been gutted by David Letterman’s presence on the picket line. In the end, some relationships were too broken to repair.

Experience First Blog

Moving Forward

While the strike took a lasting emotional toll on Mitzi, she rolled with the punches and continued doing what she did best — running her club. The comedian who participated in the strike remained “unionized” for another year, but there wasn’t much of a need. They’d changed the game and established that comics should be paid.

LA Mag / The Comedy Store

Mitzi’s Legacy

Mitzi passed away in 2018 leaving her club to her children, one of whom is comedian Pauly Shore. The strike left a blemish on the Comedy’s Store legacy, though it didn’t undo the decades of hard work and dedication Mitzi contributed to the world of comedy.

LA Times / The Comedy Store

Banned From The Club

As for Tom Dreesen and Jay Leno, they didn’t take the stage of the Comedy Store ever again. They turned to the other big LA clubs like the Laugh Factory. The sting of their rift with Mitzi taught them a valuable lesson about how friendship shouldn’t trump mutual respect. For Leno, that shifted the focus of his career.

Getty Images / Bryan Bedder / Stringer

Leno Did Things Differently

In the years before helming The Tonight Show and amassing his substantial fortune, Leno thought strategically about his future, particularly his finances. When other comics were out trying to book auditions, Jay was focused on pragmatism. That was part of the reason he took the Comedy Store strike so seriously.

Getty Images / Paul Natkin / Contributor

Focused On Saving

In the comedy world today, Leno gets heat for being a “lazy” comic, but his past paints a very different narrative. Having only enough money to survive, which is the reality for most comics starting out, wasn’t an option for Jay. Even after his bank account reached the hundreds of millions, he refused to compromise his wealth with rash spending.

Getty Images / charlie nucci / Contributor

Temptations Never Swayed Him

But the temptation was surely there for Jay; as one of late night’s most iconic and well-paid talk show hosts, he could’ve had whatever he wanted whenever he wanted it. Yet Jay knew the value of a dollar, and it was all thanks to a certain fast food restaurant.

Kevin Winter / Getty Images

Fast Food Lessons

McDonald’s. As a teenager in Andover, Massachusetts, Jay spent two years hand-cutting Mickey-D’s famous fries. It was a part-time job like any other, though one fateful day an incident in the storage room changed everything for the wide-eyed 16-year-old.

Public Affairs Books

As Jay and his boss entered to grab another bag of potatoes, they discovered that a fellow employee had used the space as a changing room… and had left a pair of underwear right on the spuds. Jay expected he’d have to toss the contaminated bag — his boss, however, had other plans.

Instead, Jay’s boss told him to throw away all the bags of potatoes near the forgotten tighty-whities. “That was very impressive to me,” Leno recalled. “The standards for quality were quite high. It was one of those life lessons I never forgot.”

WSOC TV

It wasn’t long before Jay began applying this tenet of quality to his fledgling comedy career, working tirelessly to perfect his jokes and material. But while fellow comedians were struggling to get by on meager gig pay, Jay had an ace up his sleeve.

AwardsShowNetwork / YouTube

Early on, Jay decided that the quickest way to become a millionaire was to have multiple streams of income. His nights consisted of working comedy clubs and dive bars throughout New England, and during the day, he held a steady job at a car dealership.

Wikimedia Commons

But the real genius of Jay’s approach was how he chose to spend the money he made. With his full-time job bringing in more than his comedy gigs, Jay limited his disposable income to the smaller amount, banking the dealership money and spending whatever he made doing stand-up.

Don Kirshner’s Rock Concert

“I put my money in a hammock and say, ‘You relax. I’m going to go work,'” Jay once said of his unusual saving strategy. “And when I come back, I put some more money in the pile.”

Photo by Robert R McElroy / Getty Images

As his comedy career took off and became the bigger of the two paychecks, his method reversed: the stand-up money went into his pocket, and the dealership dough was free for spending. Jay was confident he could ride this plan to retirement — then, he hit it big.

Rick Diamond / Getty Images

In 1992, Jay took over The Tonight Show for Johnny Carson and quickly became one of television’s most popular personalities. His celebrity skyrocketed higher than ever before, yet even with a seemingly endless stream of income, Jay wasn’t about to let his newfound wealth change his plans.

Alan Light / Flickr

“I pretended as if I didn’t even have the ‘Tonight Show’ job,” he explained. “You know, when you start making money, you get lazy. I wanted to make sure I always had that hunger, so I never looked… It would go directly into a bank.”

Obama White House Archives

Even as his Tonight Show salary topped $30 million, Jay was still working 150 to 200 comedy gigs a year, using his stand-up cash to support himself while squirreling away those tens of millions. Yet despite appearances, Jay was by no means a frugal man.

JBER

In 2012, he actually agreed to take a 50% pay cut to prevent members of his team from being laid off. His salary was still impressive — a cool $15 million a year — but Jay always justified his hefty price tag.

Shaan Hurley / Flickr

“I [tried] to get there early and leave the latest,” he explained. “People don’t begrudge you how much money you’re making if they think you’re working for it. You’re coming in before them and you’re supporting them and then you leave at the end of the day after they leave. I think that inspires loyalty.”

By the time Jay left The Tonight Show for good in 2014, he’d accumulated “a nice little nest egg,” and, to this day, he claims that he still hasn’t touched a single cent of his late-night money. Judging by the size of his car collection, however, that’s a little hard to believe.

NBC Universal / Walker Dalton

Over the years, Jay has aquired a total of 286 vehicles, many of which he features on his show Jay Leno’s Garage. Jay owns every single piece in his collection outright, a testament to his avoidance of one of America’s most prominent financial burdens: debt.

U.S. Army Materiel Command / Flickr

From homes to cars, Jay never borrowed a single dollar to pay for them — he doesn’t even use credit cards! “I own everything. I own my buildings. I own my cars. That way, if it ends tomorrow, I know what I’ve got,” Jay said.

Petrolicious

Even at 69 years old, Jay was still determined to maintain two incomes: one from hosting Jay Leno’s Garage, the other from doing stand-up. But while it may seem unnecessary for a man of such great wealth to work 200-plus comedy shows a year, Jay says that it’s all about peace of mind.

Shawn Miller / Library of Congress

“So many people get to be the age I’m at now and they’ve got nothing because they just blew it all,” Jay explained. “[Working at my age] sounds ridiculous, but if everything ends tomorrow, I know I’ll be fine.”

Wikimedia Commons

Jay’s saving habits almost certainly brought him some comfort during his career, especially while he was going to head-to-head with longtime frenemy David Letterman for late-night dominance. Jay could sleep soundly knowing his future was secure — Letterman’s, however, was anything but.

NBC/NBCU Photo Bank

With his gap-toothed smile, hilarious Top Ten lists, and trusty sidekick Paul Schaffer at his side, David Letterman changed the way people understood entertainment, with a TV show that made fun of TV shows. But that smile was hard to spot when cameras stopped rolling.

Letterman always had a streak of anxiety and melancholia, ever since he was a kid in Indiana. Ever the pessimist, David worried about everything. His dad, who was often in poor health, was an ongoing concern and died while David was only in his teens.

Although he was never a star student or social butterfly, Letterman did show a knack for humor. During his college years at Ball State University, he cracked up classmates by doing funny announcements on the college classical radio station. Unsurprisingly, he got fired.

Ball State University

Despite Letterman’s talent, Indiana had no idea what to do with him. He actually got his start in TV as a weatherman. After he cracked up viewers by riffing on malfunctions and announcing forecasts for fictitious towns, Dave got offers to host other local programs.

Taking a big gamble, Letterman moved out to Los Angeles. For once, things seemed to go right. He quickly ingratiated himself in the booming stand-up comedy scene and landed guest spots on popular TV shows — including The Tonight Show Starring Johnny Carson.

NBC

The great Carson, who could make or break any comic’s career, took an instant liking to Letterman. Besides bringing him back a number of times as a guest and fill-in host, Carson helped give Dave a place to experiment with his dry, ironic sense of humor.

Wikimedia Commons

Letterman got his own NBC talk show in 1980, at first in the morning, and eventually in the late slot directly following Carson. The host developed a cult following for his anything-goes attitude and habit of openly quarreling with guests. Fans presumed he’d someday take over for Carson.

Paul Drinkwater / NBC

Letterman himself looked forward to this promotion too. By the early 1990s, the rumor mill was swirling with talk of Carson’s imminent retirement. While the Indiana troublemaker readied himself for primetime, NBC suits worried Letterman was too weird and caustic for mainstream audience.

Wikimedia Commons

So the executives pulled a coup. They instead hired the crowd-pleasing Jay Leno, Dave’s longtime friend who came to prominence in large part because Letterman frequently booked him as a guest. As the ultimate insult, NBC said Letterman could follow Leno.

NBC / YouTube

However, Letterman couldn’t remain with a company that had betrayed him. He took a juicy offer to host his own program on CBS, which would go head-to-head with Leno’s Tonight Show. Every newspaper and magazine was abuzz about this late night comedy war.

Alex Proimos / Wikimedia Commons

In contrast to Leno’s safe topical jokes and desk gags, Letterman went wild. He and his staff entertained audiences with all kinds of stunts, whether Dave was working a Taco Bell drive-thru or tossing watermelons off the roof. These antics rubbed some viewers the wrong way.

Instagram / David Letterman

Leno did manage to get a larger audience most weeks, but Letterman had all the critics on his side. In addition to racking up awards, TV viewers perceived him as the “cool” host, the one who was genuinely funny and driving the cultural conversation.

David Letterman / Instagram

But Dave never felt like the success people made him out to be. He spent most workdays fretting that he wasn’t funny and that his staff wasn’t coming up with anything good. In his later years, he became reclusive and barely interacted with writers at all.

Pete Souza / Wikimedia Commons

In stark contrast to today’s TV personalities, Letterman never shared much about his private life or embraced his own celebrity. He only made sporadic appearances outside The Late Show, like a cameo in his pal Chris Elliott’s movie Cabin Boy or his ill-fated Oscars gig.

Touchstone Pictures

When Dave got the job hosting the 1995 Oscars, it seemed like a match made in heaven. From his opening monologue onward, however, the event fell apart. Celebrities in attendance didn’t enjoy being openly mocked, and Letterman’s Late Show bits translated poorly to this grandiose awards ceremony.

The Academy of Motion Pictures Arts and Sciences

But Letterman’s lowest moment came in 2009. The host had a history of flings with female staffers, and one former lover named Stephanie Birkitt came after him. She and her boyfriend blackmailed Letterman — now happily married — for $2 million.

CBS

The host was having none of it. Late Night viewers were shocked when Dave apologetically confessed to these affairs on-air and revealed the blackmail plot. Letterman wasn’t going to let anyone shake him down, plus he wanted to show everyone he was a changed man.

Wikimedia Commons

Becoming a father later in life, Letterman had his whole world turned around by Harry. That parental role gave him a new purpose while also brightening his cloudy worldview. And as a dad, Dave realized he couldn’t devote his life to TV forever.

Dave decided to leave The Late Show in 2015, and his final months were marked by a flood of celebrity appearances and the revival of classic bits. Tearful fans wondered what they’d do without Letterman every night. Fortunately, he didn’t just ride off into the sunset.

David Letterman / Instagram

Letterman sporadically returned to showbiz on his own terms. He hosted long-form interviews for Netflix and inducted Pearl Jam, one of his favorite bands, into the Rock and Roll Hall of Fame. Dave even grew a Civil War-style beard, a final farewell to the man he once was behind the desk.

David Letterman / Instagram