Summary of Jay Leno | The Blocks Podcast w/ Neal Brennan | FULL EPISODE 26

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00:00:00 - 01:00:00

In this episode of "The Blocks Podcast," Neal Brennan interviews Jay Leno and they discuss various aspects of Leno's career in comedy. They talk about the challenges Leno faced in his early days as a comedian, his approach to comedy and money, his time hosting The Tonight Show, and his relationship with other comedians, including David Letterman. Leno reflects on the importance of hard work, seeking out constructive criticism, and not taking jokes or criticism personally. He also discusses the late-night rivalry with Letterman and their dynamic on their respective shows. Overall, Leno shares insights into his mindset, the hustle required to succeed in comedy, and his contentment with his career.

00:00:00 In this section, Neal Brennan introduces the concept of his podcast "Blocks" and explains how he invites guests to talk about what makes them feel alone in the world. He acknowledges that Jay Leno may not relate to this topic as much, but Leno responds by expressing his empathy and understanding for comedians who use their flaws as a crutch and commends Brennan for his ability to convey genuine emotions on stage. Leno also mentions the bravery in portraying pain and suffering authentically, rather than in a phony way. Brennan brings up how stand-up comedy has evolved and Leno recalls a time when he opened for Richard Pryor, highlighting the intense and competitive environment in which comedians used to perform.
00:05:00 In this section, Jay Leno talks about his early days as a comedian and the challenges he faced. He mentions that he initially didn't have enough material to do a full hour set, but he understood the importance of making people laugh every six to nine seconds. He also talks about the comedy scene in the late 60s and early 70s, where there weren't many comedians and no dedicated comedy clubs. Leno recalls performing in strip clubs and even sharing the stage with strippers, recounting a memorable incident where a stripper defended him against a heckler by breaking the heckler's nose. Overall, Leno reflects on the hustle and determination required to make a living as a comedian during that time.
00:10:00 In this section, Jay Leno reflects on his early days in stand-up comedy and the challenges he faced. He talks about how he discovered that there were many people in Los Angeles who also wanted to be comedians, which was different from his experience in Boston. Leno also mentions meeting Al Franken and Tom Davis, two aspiring comedians from Harvard. He explains that his attraction to comedy was instinctual, much like a kid discovering his attraction to girls. Leno also shares a personal story about his father teaching him to box and how he learned to "take a beating." He discusses his early comedy gigs, such as performing at Playboy clubs, and the financial struggles he faced as a comedian. Leno emphasizes that even though his career has brought him success, he still thinks about money and living within his means. He also mentions being dropped by his talent agency, ICM, and how he eventually became the host of The Tonight Show.
00:15:00 In this section, Jay Leno discusses his belief in low self-esteem being the key to success and the importance of seeking out constructive criticism. He emphasizes the value of listening to strangers' opinions rather than friends or loved ones, as they are the ones who truly keep the lights on. Leno also talks about his approach to comedy, explaining how he would try out jokes on the weekends and bring them back to The Tonight Show, finding that the audience's reaction was bigger than the written jokes. He mentions his dislike for a scripted monologue and the importance of authenticity in comedy. Leno's insights shed light on his mindset and approach to his career.
00:20:00 In this section, Jay Leno talks about his approach to comedy and money. He explains that he doesn't worry about running out of money because he enjoys working and sees it as a way to keep his mind sharp. He shares a technique he uses on stage, where he recites the Pledge of Allegiance while thinking about his jokes, giving the illusion of spontaneity. Leno also mentions how watching Johnny Carson influenced his mindset on money, as he saw Carson's relatability when he expressed surprise at the price of Dean Martin's shoes. Leno concludes by saying that he values the act of working more than the amount of money he earns, and as long as his savings remain steady, he is content.
00:25:00 In this section of the interview, Jay Leno discusses the importance of challenging oneself as a comedian and not just sticking to places where you know you'll get laughs. He talks about how he booked himself into very different venues, like Oral Roberts, to see if he could still make a diverse audience laugh without relying on obscenities or shock value. Leno also shares his experience working with David Letterman, describing the natural and funny dynamic they had and how they would make each other laugh. He expresses that doing Letterman's show was the most fun he ever had in show business.
00:30:00 In this section, Jay Leno discusses his time hosting The Tonight Show and the challenges of being a comedian in that role. He shares how he had to know when to let jokes go and not offend guests, as well as the pressure to keep the show light and entertaining. He also talks about his approach to hosting and how it was a job rather than an extension of his identity as a comedian. Leno also reflects on the criticisms he faced from other comedians and his willingness to watch and find humor in their failed sets. Overall, Leno emphasizes the importance of understanding the nature of the job and not taking it personally when faced with criticism or jokes at his expense.
00:35:00 In this section, Jay Leno discusses his experiences with other comedians who made fun of him and how he dealt with it. He shares a story about calling a comedian who didn't like him and explaining the consequences of trashing his work. He also talks about his relationship with Bill Hicks and how Hicks resented him for being more successful. Leno recalls a situation where Hicks wanted to perform his controversial Jesus bit on The Tonight Show, but Leno advised against it due to censorship issues. This led to tension between them, and Leno reflects on whether he handled the situation correctly. Overall, Leno doesn't regret his actions and believes he would handle things the same way if given the chance.
00:40:00 In this section, Jay Leno reflects on the late-night rivalry between himself and David Letterman. He mentions that when he guest hosted, he got the same ratings as Johnny Carson, which made NBC realize that they had a hit at 11:30 with Jay. However, they didn't want to risk moving Letterman to an earlier time slot because there was no guarantee it would be successful. Leno admits that although he loved Letterman, there were times when he was hurt by certain things, but overall, he felt they were a great comedic duo and always left conversations with Letterman with more material than he came in with. Leno also mentions that they have very little in common aside from their shared love for cars and their enormous wealth.
00:45:00 In this section, Jay Leno discusses his relationship with David Letterman and the dynamic they had on their respective shows. Leno mentions that he always enjoyed appearing on Letterman's show because it was spontaneous and they didn't have to run their material past anyone. Leno also expresses his gratitude for their friendship and the impact it had on his career. He believes that if they were in a comedy team, Letterman would be the straight man and he would be the clown. Leno admires Letterman's skill with words and acknowledges that they both learned from each other. He concludes by saying that he would always be there for Letterman if he ever needed him for anything.
00:50:00 In this section, Jay Leno addresses the misconception that he took "The Tonight Show" away from David Letterman. He explains that it was David's own success that prevented him from getting the show, and he had actually been hosting for five years before taking over. Jay also talks about falling in love with his wife Mavis and how they never had kids because she didn't want them. He shares that their relationship is like being on a perpetual date and they enjoy each other's company. Jay also discusses his recent accidents and explains that accidents happen and they don't necessarily teach you anything. Lastly, he talks about still hosting TV shows, including "Jay Leno's Garage," of which he has done over 500 episodes.
00:55:00 In this section, Jay Leno discusses his experience running a staff and hiring writers for his show. He mentions that he didn't find it stressful because everything was going well for him and his parents got to see him be successful. He liked having a staff and enjoyed working with them. He hired writers based on their material and had two teams working different shifts to provide jokes. Leno also talks about his temper, or lack thereof, and how he values kindness and hard work in the workplace. He mentions that he took the smallest office and focused most of his effort on the monologue. He discusses his acceptance of the turnover in showbiz and his contentment with the 22-year run of The Tonight Show. Leno emphasizes that he didn't aspire to live a typical show business lifestyle.

01:00:00 - 01:20:00

Jay Leno reflects on his competitive nature, his experience as a talk show host, and the criticism he has received. He discusses his ability to appreciate other comedians' talent, his approach to creating jokes, and the challenges of appealing to a wide audience. Leno also shares his thoughts on handling criticism from fans and fellow comedians, his favorite movies, and his perspective on the meaning of life. He emphasizes the importance of relationships and experiences over material possessions and the value of a grounded and non-neurotic approach to life.

01:00:00 In this section, Jay Leno discusses his competitive nature and how he doesn't mind getting beaten by someone who is better. He shares a story about seeing comedian Arnie Adams perform a bit that he wished he had come up with himself, showing his appreciation for other comedians' talent. Leno also talks about his ability to recognize when someone is not being authentic in their comedy and how he can tell when they don't like a joke. He gives examples of late night hosts who display this. Additionally, Leno mentions his joke about locking a finicky cat in a closet, which inspired the comedian Neal Brennan to create his own joke about dogs as hostages.
01:05:00 In this section, Jay Leno discusses his experience as a talk show host and the challenges of trying to appeal to a wide audience. He shares that he would include both smart and silly jokes in his monologue to cater to different tastes. Leno mentions that he often received criticism for the silly jokes, but was quoted more for the political ones. He also talks about the difficulty of expressing opinions as a talk show host without alienating viewers. Leno mentions a conversation with Colin Powell, where Powell explained that he didn't run for president because he would lose a significant portion of the audience every day due to differing beliefs. Leno reflects on the criticism he received, expressing surprise and noting that it can be challenging to see oneself in a different light when others have opposing opinions. Despite this, Leno considers himself to have a thick skin.
01:10:00 In this section, Jay Leno discusses the criticism he has received from people he doesn't know, such as fans and comedians. He shares an example of Bobcat Goldthwait setting a couch on fire during an appearance on The Tonight Show, and how he defended Bobcat when authorities wanted to arrest him. However, he later hears Bobcat criticizing him on The Howard Stern Show and is disappointed by his lack of gratitude. Despite the hurtful criticism, Jay Leno doesn't let it affect him for long and believes that what doesn't kill you makes you stronger. He attributes his resilience to always being grateful for his success and not feeling sorry for himself.
01:15:00 In this section, Jay Leno discusses some of his favorite movies, including "Requiem for a Heavyweight" and "A Face in the Crowd." He also mentions "The Godfather" and "12 Angry Men" as great movies. Leno's favorite Christmas movie is "Miracle on 34th Street" because it gives a logical reason for Santa Claus to exist. When asked about his own movie, Leno dismisses it and says he doesn't really care about his own story arc or the idea of leaving a legacy. He simply enjoys making people laugh and doesn't spend much time thinking about deeper meaning or personal growth.
01:20:00 In this section, Jay Leno reflects on the true meaning of life and the things that matter to him. He shares that when he thinks about what he would regret on his deathbed, it wouldn't be the material possessions or places he could have bought or visited. Instead, he realizes that he missed the whole point of life by focusing on things like buying cars (he currently has 204 on the road) and not fully appreciating the experiences and relationships. Leno acknowledges that his perspective may seem unconventional, but he sees himself as lucky rather than special. He also emphasizes the importance of having good friends, a strong support system, and a stable marriage of 43 years, as these are the things that truly matter to him. He is able to separate work and personal life, not letting outside forces affect him, and he values the peace and harmony at home. Leno's grounded and non-neurotic approach to life allows him to move forward and not overanalyze the reasons behind his actions.