You can’t talk about late-night TV without mentioning The Tonight Show, and you can’t mention The Tonight Show without talking about Jay Leno. A powerhouse in Hollywood, Leno’s rise to fame wasn’t a smooth ride. Drama dogged him every step of the way, and he didn’t always win his battles. He also happened to be at the center of not just one, but two of late-night’s most controversial feuds. From his losses to his triumphs, this is the wild career of Jay Leno.
1. His Parents Were Tough
Born on April 28, 1950 in New Rochelle, New York, Leno learned how to be tough and hardworking from his parents. His mother, Catherine Muir, was a Scottish immigrant and no-nonsense stay-at-home mom. His father, Angelo Leno, was an insurance salesman. Sounds boring, right? But here’s the thing: He sold insurance in Spanish Harlem, one of the most dangerous parts of NYC at the time.
Both of Leno’s parents tried to raise him to be a good kid, but let’s just say they got mixed results.
2. He Was A Bad Student
During high school, Leno scored himself a job at McDonald’s, but believe it or not, he didn’t have plans to stay there forever. Unfortunately, his high school guidance counselor didn’t agree. During a Career Day meeting, the counselor actually suggested that Leno should work at McDonald’s for the rest of his life, stating, “Sometimes students are better off doing jobs and menial tasks.” Ouch!
In an ironic twist, the counselor was at least partially right—McDonald’s actually launched his comedy career.
3. McDonald’s Got Him Started
During his tenure at McDonald’s, Leno discovered that the company hosted a regional talent show. His manager urged him to join, saying, “Look, you’re a funny guy. Why don’t you put together a comedy routine for the show?” Leno did, and ended up winning the competition by telling jokes at McDonald’s expense. Inspired by his success, he soon took his first steps into the world of comedy.
4. His First Audition Was Disastrous
Leno got his first chance to perform at a venue called The Bitter End in Greenwich Village, but he had to audition first. On the day of the audition, he ran into a major setback: He had a sore throat. Someone backstage handed up some Chloraseptic spray to help with his sore throat, and innocent young Leno spritzed his throat ten times, not realizing that the spray numbed his entire mouth.
He got onstage—and his audition was a total disaster.
5. He Got A Second Chance
Leno got onstage to do his routine, even though he sounded like he was speaking around a mouthful of cotton the entire time. NYC comedy audiences are infamously tough, and you can bet this didn’t go over well. Luckily for Leno, the owner of The Bitter End took pity on him and invited him back to audition again the following week. His second audition went much better, and it landed him his first real gig. Knowing Leno’s luck though, you can bet that his first gig was also a complete fiasco.
6. Disaster Struck Again
Unbeknownst to Leno, his father, proud that Leno managed to achieve something in life for once, called up all his relatives in New York to come see Leno’s routine. When Leno got on stage, he was surprised—and horrified—to see his family members in the audience, which included a religious uncle and his two young daughters. Leno’s routine was not at all child-friendly, and needless to say, his uncle didn’t show up to Leno’s next gig.
Still, Leno’s intended audience seemed to connect with him. As he found more and more success with his gigs, lady luck finally started smiling on him.
7. He Almost Lost His First Big Role
In a twist of fate, Leno bumped into director Ivan Passer at The Comedy Store in Los Angeles. Passer immediately told Leno that he had “a good face for a movie,” and asked him to join his project. Leno, in a surprising move, refused the role. You see, directors had offered him movie roles before, but they had all turned out to be scams. A second chance meeting was the only thing that kept Leno from losing out on this career-changing opportunity.
8. The Director Was Tenacious
Passer really, really wanted Leno in his upcoming movie, Silver Bears. A couple of days later, Leno bumped into Passer again, and this time, Passer gave him the phone number to the production office. Leno realized that this was the real deal, so he jumped at the chance to actually act in a film. Silver Bears saw Leno working alongside big names like Michael Caine and Cybil Shepherd, and it was the movie that led to him meeting his biggest hero.
9. He Met His Hero
On March 2, 1977, Leno made his first appearance on The Tonight Show to promote Silver Bears. This was a huge deal for the up-and-coming stand-up. The Tonight Show launched the careers of many comedians before him, and the host, Johnny Carson, was one of his personal heroes. Leno performed his routine, and even got some pointers from Carson on how to improve.
Leno ended up appearing on the show several more times. After a rocky start, it felt like he was in heaven—until he hit a major roadblock.
10. He Got Complacent
Leno fell into the same trap many amateur comedians did on The Tonight Show. He spent his first show performing all his best work, then spent subsequent shows using material that was less-than-polished, then very quickly ran out of material after that. It was a valuable lesson learned for Leno: A comedian is never “finished” writing jokes.
As Leno continued to improve his work, other shows started noticing his talent, and his career really started to ramp up.
11. He Inspired David Letterman
Starting in 1982, Leno appeared on numerous episodes of NBC’s Late Night With David Letterman. Leno always felt a bit awkward around the more established, older comedians, but with Letterman, someone around his own age, he could really ham things up with his off-the-wall humor and mock outrage. In fact, Letterman loved getting Leno riled up so much that it inspired the “What’s Your Beef” segment of the show, which featured Leno riffing on whatever he found outrageous that day.
Leno did so well on Late Night that it caught the eyes of some NBC bigwigs—and put him on the path to stardom.
12. He Impressed The Right People
Leno’s ability to connect with a younger audience through his humor caught the attention of NBC executives at The Tonight Show. They invited Leno on as a regular guest host to fill in when Carson went off on vacation. Leno, ecstatic to be hosting for one of the biggest shows on late-night television, said yes. Of course, this wouldn’t be a story about Jay Leno without something going horribly wrong on his first day.
13. No One Believed Him
On Leno’s first day as a guest host on The Tonight Show, guards barred him from entering NBC Studios. It was ridiculous, but they didn’t believe this person they’d never seen before was hosting! In fact, most employees at NBC didn’t believe he was a regular guest host, even after he had several shows under his belt. An interviewer at an NBC affiliate station actually once introduced him as, “Jay Leno, who claims to have hosted The Tonight Show.”
14. His Manager Took Over
Leno soon came under Helen Kushnick’s wing. Kushnick became Leno’s agent and championed his cause. She worked hard and had the smarts to propel Leno’s career forward. On the surface, it seemed that Kushnick had the ability to focus Leno’s career and give it an end goal. That goal was to make him the new, permanent host of The Tonight Show. Simple, right? Well, underneath the surface was a darker story.
15. She Controlled Him
Those working around Leno soon noticed that his relationship with Kushnick wasn’t on equal terms. Kushnick had a tight rein on Leno’s public persona, and refused to let anything outside of comedy and hosting The Tonight Show distract him. Once, when Leno tried to suggest something new, Kushnick snapped at him that “You don’t get paid to think. I’ll think.”
Despite her behavior, she was doing a lot for his career, and soon, a golden opportunity presented itself to them.
16. He Got His Chance
After decades of having the aging Carson host The Tonight Show, NBC executives decided it was time for a new host. NBC ultimately narrowed it down to Leno or Letterman. In response, another studio, CBS, swooped in and offered Leno a $6,000,000 contract to do a show on their network instead. Despite the amazing offer, Leno had his heart set on The Tonight Show, and did all he could to convince NBC that he was the right man for the job.
17. Leno Won…At A Cost
In 1991, NBC announced Leno as The Tonight Show’s next successor. This caught most people by surprise. Everyone in the industry, including Carson himself, thought Letterman would be a more natural successor. Letterman, in shock, left to host a competing show at CBS. Carson, who saw how toxic Kushnick’s influence was becoming, gave Leno an ominous warning: Be careful of those who work for you.
It was a warning that Leno failed to heed.
18. Something Wasn’t Quite Right
Leno took over as host for The Tonight Show, but critics and staff members noticed something just seemed off about his performance. One NBC executive thought that Leno seemed to be having trouble expressing his emotions to the audience and connecting with guests on the show. Others put it off as jitters, or pressure from having to do a show every night. His staff had an even darker theory.
19. He Was In Denial
It quickly became clear to staff members that Kushnick, now executive producer of The Tonight Show, was too heavy-handed in her control over Leno. One staff member remarked, “She was so vicious to him in public and in private that I assumed they had a relationship that I couldn’t possibly understand.” Every time a staff member called her out, Leno, in denial, just pointed out that the show still brought in good ratings.
Things at work were getting tense—but soon a horrible tragedy put everything in perspective.
20. He Lost His Parents
In the same year that Leno took over The Tonight Show, doctors diagnosed his mom with lung cancer. She didn’t make it past the following year. His dad rapidly deteriorated after his mom’s passing—as Leno put it, “He sort of lost his own will to fight.” Soon, Leno lost his dad as well. However, Leno never truly saw his parents as gone for good, saying, “I’ve got all of their stories and that keeps them nearby always.”
21. He Did A Show In The Dark
From 2000 to 2001, California faced an energy crisis that forced rolling blackouts throughout the state. This put The Tonight Show into hot water when the blackouts hit them too. With no studio lights, Leno once did an entire show in the dark with only flashlights and candles on set. Although the episode didn’t end up airing, Leno and his team managed to keep the energy of the audience up for a successful show.
Leno’s ability to make the best of things came in handy when he, along with the rest of America, faced one of the darkest moments in the nation’s history.
22. He Took The Show Off The Air
The September 11 attacks marked one of the worst tragedies in American history. For the first time since the show’s inception, Leno took The Tonight Show off the air for about a week, in solidarity with other similar talk show programs. In light of this tragedy, the press faced Leno with a huge question: Should his show, with its lighthearted sense of humor, air during such a dark time? A week later, Leno gave a surprising answer.
23. He Faced Tragedy Head-On
The Tonight Show’s first episode to air after the September 11 attacks was a subdued and solemn one. Leno opened the show by paying tribute to the rescue workers across America, as well as to those who lost their lives. As for the show’s naysayers, Leno explained that he wanted the show to be a bright spot in people’s day—a way to escape from reality, just for a moment.
24. He Swapped Jobs For A Day
On May 12, 2003, day-time news anchor Katie Couric proposed a little publicity stunt: She and Leno would swap jobs for a day. That evening, Couric hosted The Tonight Show, while Leno acted as the news anchor for Today. Critics expressed some heavy skepticism—did Leno really have the political acumen needed to fill in as a news anchor? Leno’s performance ended up surprising critics and fans alike.
25. He Shocked His Audience
Leno ended up shocking his critics with his well-thought-out, pointed, and intelligent questions. He asked the then-Secretary of State Colin Powell several charged questions about foreign affairs and even managed to read off of a teleprompter, despite his dyslexia. Throughout his career, Leno seemed to have an uncanny ability to cope with just about anything—but that doesn’t mean wild guests didn’t test him.
26. His Stage Was Set On Fire
Just two years into his tenure as host, an unforgettable guest arrived at his studio. Comedian Bobcat Goldthwait, in the middle of his interview with Leno, set his guest chair on fire as a joke. Leno, cool as a cucumber, just sighed and put out the fire with his cup of coffee, before forcing Goldthwait to sit back down on the half-burnt, coffee-drenched chair.
It was a memorable episode of television—but it was far from the most scandalous moment on Leno’s show.
27. A Guest Showed Up Wasted
During the same year that he swapped places with Couric, Leno had famed director Quentin Tarantino on The Tonight Show. Tarantino was supposed to promote his movie, Kill Bill, but he couldn’t due to a ridiculous reason: The Tonight Show had an open bar at the green room, and Tarantino indulged a little too much. Leno spent most of the interview keeping a clearly wasted Tarantino from going completely off the rails.
Say what you will about Leno, but he consistently proved himself to be a capable host—even when, two years later, he got some devastating news.
28. He Lost His Hero
January 23, 2005, proved a dark day for all those in the world of television. It was the day of Johnny Carson’s passing, and it rocked the world of American TV. For Leno, who looked up to Carson as a hero, this news was a huge blow. Despite their rocky history, there was no question that Carson shaped Leno’s career. As a gesture of respect, Leno did the only thing he could do as the host of The Tonight Show.
29. He Honored His Career
Leno dedicated an entire episode to the life and career of Johnny Carson. He opened the show with a monologue honoring him, and stated, “As a performer, I don’t think I ever wanted to impress anyone more than Johnny Carson. He had that effect on all comedians.” As the show continued, each of the guests shared fond memories of working with Carson. It was a fitting way for Leno to pay tribute to his personal hero and predecessor.
30. He Put His Head To Good Use
In 2005, the courts called on Leno to testify in Michael Jackson’s trial. As a result, Leno could not talk about the case on The Tonight Show, nor could he make jokes about Jackson. With the trial being the hottest topic on television, Leno couldn’t afford to not talk about it on the show, so he and the team put their heads together…and they found a legal loophole. Needless to say, they exploited the heck out of it.
31. He Technically Followed The Law
Even though Leno himself couldn’t talk about Jackson, he and his team realized that they could still feature jokes about Jackson on The Tonight Show…as long as other people presented the jokes for him. Leno brought on several guest comedians to make jokes about Jackson while he himself stood off to the side, laughing along with the audience.
Later, the courts lifted the gag order. Leno dedicated an entire section of his show to Michael Jackson jokes in celebration.
32. The Show Faced Danger
Real danger entered The Tonight Show’s set on July 20, 2006. In the middle of Leno’s interview with Colin Farrell, Farrell’s stalker, Dessarae Bradford, evaded NBC’s guards, broke onto the set, and confronted Farrell as the cameras rolled. Bradford was escorted out of the studio and handed over to the authorities, as Leno sarcastically called for “a round of applause for NBC security.”
At the time, his remarks seemed to be a small, if pointed, jab at the studio he worked for, but it revealed a deeper issue in the company.
33. He Found Another Passion
After his long tenure as the host of The Tonight Show, Leno found success elsewhere. Even during his Tonight Show days, professionals in the automotive industry recognized Leno as an automotive authority—he had a private collection of rare and expensive cars, and wrote several articles about them. It’s no surprise then that Leno has moved to YouTube, and is now hosting a show called Jay Leno’s Garage. At 70 years old and still going strong, Leno continues to entertain viewers all over the world.
34. He Never Used His Tonight Show Money
Throughout the entirety of his career at The Tonight Show, Leno continued to do stand up performances, effectively earning dual incomes. He made a point of never spending everything in one place, however. He only ever spent his income from his stand up shows, safely banking away his income from The Tonight Show for a rainy day. As such, his current net worth is sitting at $450,000,000.
35. He Barely Sleeps
With all of his various projects and shows, Leno barely gets time to sleep—and he claims he doesn’t need it. Between the stand-up, the shows, charities, and writing for various publications, Leno gets as little as four to five hours of sleep each night. It’s not surprising then that he once went to the hospital and stayed there for two days due to exhaustion. It was the only time NBC canceled the show since Leno took over.
36. His Staff Fought Back
On November 5, 2007, all 12,000 members of the Writer’s Guild of America went on strike. Guild members demanded better work conditions and wages, which several studios, including NBC, refused to grant. Leno, for his part, backed members of the Writer’s Guild, even going so far as to bring donuts and coffee to the picket lines to keep the spirits of the strikers up.
Despite this, his other actions both alarmed and confused members of the guild.
37. He Made A Promise
Leno had 80 staff writers for The Tonight Show, all panicked at the thought of losing their jobs. In response, Leno told them not to worry, saying, “I can’t get into details, but nobody will miss a car payment or lose their house. We’re family. Trust me. I’m going to take care of this.” It was a huge relief for many of the writers. A couple of days later, his promises proved empty.
38. His Plans Fell Through
NBC hit Leno’s writing staff with devastating news: They were all fired. Leno failed to uphold any of his promises to them. It shouldn’t be surprising, then, that many of his staff turned on him. At best, Leno was naive and optimistic. At worst, he wasn’t taking their plight seriously at all. Leno even started continuing the show without them!
Despite the bad press, he continued to bring in viewers to the show, and the guild just couldn’t touch him. He seemed unstoppable…until it all came crashing down.
39. They Hit Him With Devastating News
During contract negotiations with NBC, executives dropped some terrible news on Leno: At the end of 2009, The Tonight Show would go to Conan O’Brien, who hosted another NBC talk show, Late Night With Conan O’Brien. Leno’s audience was getting older, and they needed to bring in a new talent to attract a younger audience.
Leno made a public statement that he would pass the show onto O’Brien as peacefully as possible. In private, his reaction was much different.
40. He Was Heartbroken
Leno was absolutely incredulous that NBC would end his reign as host so abruptly. He started scheming to keep his job—he even hid in an NBC executive’s closet to eavesdrop and dig up dirt. Eventually, he got so upset, that he started telling staff that, once his tenure ended, he would take everyone down to ABC, a competing network, and offer to work for them instead. But at the same time,
News of this made its way back to NBC executives—and they panicked.
41. They Made The Ultimate Offer
Not wanting to lose Leno to another studio, NBC gave him an offer he couldn’t refuse: After he finished hosting The Tonight Show, he would get another show—one that would come on right before The Tonight Show. All Leno had to do was to make sure he didn’t book the same guests or be too similar to O’Brien’s show. Ultimately, Leno agreed to the offer. The results were catastrophic for everyone.
42. Both Shows Flopped
After Leno handed The Tonight Show over to O’Brien, The Jay Leno Show premiered on September 14, 2009. Soon, NBC had a huge problem on their hands: Both shows were doing poorly, and ratings were going down. The ratings were actually so low that it affected other shows on the network, all of which reported lower viewership than usual. In order to save their ratings, NBC suggested a drastic measure.
43. They Brought Him Back
In order to keep ratings from tanking further, NBC executives planned to shift The Jay Leno Show to The Tonight Show’s timeslot at 11:35 PM, pushing The Tonight Show into the next day at 12:05 AM. O’Brien refused to go along with the plan, believing that moving The Tonight Show to a later timeslot, after so many years of having it start at 11:35 PM, was unacceptable.
After just seven months on The Tonight Show, O’Brien left in protest and Leno came right back. It was just like nothing had happened at all, right? Not exactly…
44. Things Kept Getting Worse
Despite Leno’s return to his old post, ratings continued to drop. He wasn’t pulling in the huge viewer counts he used to either, and NBC was losing money. Although this wasn’t solely Leno’s fault, what he did next sealed his own fate. On April 3, 2013, Leno made a joke about NBC’s poor performance on the air. This was the last straw—NBC announced Leno would retire the next year. Jimmy Fallon became his successor.
45. She Made Enemies
Leno’s tenure on The Tonight Show eventually came to an ignominious end, but it almost happened a lot earlier. In the early 90s, The Los Angeles Times broke a story about Helen Kushnick strong-arming celebrity guests into appearing on The Tonight Show. This, combined with her poor treatment of Leno and his staff, made one thing clear to NBC executives: Kushnick had to go. And yet, Leno still refused to fire her. Their ratings were still fantastic, as Leno stubbornly pointed out.
In response, one executive warned him, “It doesn’t matter. You’re approaching disaster.” As it turned out, they were right.
46. They Tried A Hail Mary
In a last-ditch attempt to please everyone, Leno asked executives to write up a new agreement with Kushnick. She could stay as an executive producer, but lost all power to book guests, cancel guests, or talk to the media. Kushnick lost her mind and flat-out refused their proposal. An executive who was present watched as she “changed from a cool, controlled, rational person to someone screaming and out of control in a matter of seconds.”
It was a devastating blow for NBC executives. Desperate, they decided they needed to knock some sense into Leno’s head—so they came up with an ultimatum.
47. They Threatened Him
They gave Leno a simple choice: Either get rid of Kushnick or lose his job to Letterman. The chance of having this amazing job taken away from him shocked Leno into reality. On Monday morning, the executives handed Kushnick an official letter of dismissal. In response, Kushnick stormed into Leno’s office, screaming at him and trying to emotionally manipulate him into keeping her around.
However, Leno stood firm, and Kushnick had no choice but to leave. After her dismissal, Leno was left to pick up the pieces.
48. He Pulled Everyone Together
Leno’s first order of business was to apologize to everyone on his team. He apologized for Kushnick’s behavior, taking full responsibility for being so unaware of what was happening around him. From then on, the show never got another formal executive producer—Leno took the reins as an unofficial producer, gaining more responsibility and control over the show.
49. He Walked Off The Show
The most controversial episode of Jay Leno’s career aired on November 30, 1995, when Howard Stern made an appearance on The Tonight Show. He brought along two bikini-clad actresses, and in a move that even caught Leno off-guard, directed them to kiss in front of the cameras. Leno hastily tried to continue the show, only for Stern to start sucking on one of the young ladies’ toes. The audience went nuts, cheering raucously and encouraging his antics.
Leno, outraged, walked off the set. The next day, Leno mercilessly ripped into Stern.
50. He Was Livid
NBC edited out the notorious kiss for home viewing, but Leno was livid with Stern. The next day, Leno got a hold of Stern and berated him for ruining the show with his shock tactics and debauchery, stating that he was “disappointed” and “didn’t find the bit funny.” Unsurprisingly, Leno never invited Stern onto the show ever again, although Stern tried to bait him into several public feuds over the years.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25