#jay leno

I missed out on peak Johnny. But I have watched a bunch of those compilation videos with highlights from the show. I mean, I used to watch the 3am infomercial for those compilation videos. So I feel like I am still qualified to analyze him as a long-time student of comedy.

I started becoming aware of comedy right as Johnny was retiring. I literally studied it like a subject at school while not studying actual subjects at school. And the late night shows were some of the best learning tools available (aside from getting stand-up specials from Blockbuster). You got to see comedy every night and a variety of comedians with different styles.

Johnny was the best at the traditional late-night monologue. It's not that the jokes were funnier. Honestly, it is impossible to write 5 minutes of stand-up in a day that can give you anything more than a chuckle. But the audience knows that and it causes something I call "forgiveness comedy." People will adjust what they think is funny depending on the circumstances. If they know you had a day to write something, the audience will consider that and be primed to laugh more at less funny material. Especially if they like the comic.

The best example is improv. An audience will forgive the joke quality just because they are amazed it is coming straight off the dome (that isn't always true, improv is more magic trick than spontaneity, but that is another post). But if you tried to perform that same improv as a polished stand-up act, it would likely bomb. The brain adjusts to context.

Johnny took advantage of this and where he really shined was in between the written jokes. His bombs were opportunities. He would react with some self-deprecating remark and get a bigger laugh for making fun of his shitty joke. Basically, when Johnny was in trouble he was at his best. His reactions were what made him so loved.

His most famous reaction-style comedy was probably the tomahawk demonstration. I think this was one of the longest sustained audience laughs in history—which, sadly, the video cuts off. I think it was 4 minutes total.

Johnny was also a very good interviewer in the sense that he knew when to give people space. He didn't try to compete with all the funny people he invited on. He was a comedy support system and only stepped in when things went off the rails.

There were also his masterful softballs. (Sorry, I should explain I came up with my own comedy terms. They may or may not be actual comedy parlance.)

A softball is an easy setup for a joke (large balls are easier to hit). A conversational premise without a punchline. If you are riffing with another comedian and you know their strengths, you can set them up for a joke and let them take the punchline. This is a thankless comedy skill because you are giving away the glory to someone else. But being good at softballs often takes more creativity and skill than coming up with the punchline. Johnny knew he was speaking with some of the funniest people on the planet. And their success was his success. So he was always happy to set people up for hilarity.

Johnny was also a good sport. His friends would come on and make fun of him and he often laughed the loudest of anyone. Or pretended to be hurt for extra laughs. Rich Little and Tom Smothers would do impressions of Johnny in front of Johnny. I think this helped popularize the Friar's Club roasts around that time, of which Johnny was a roastee.

Johnny got along with everyone. I think the most endearing thing about his Tonight Show was that he was just trying to make sure everyone had a good time. It was fun. It was chill. It was comfort after a long day, like a television version of a warm hug. Many people would joke that is how they fell asleep each night.

There was one aspect of his show I have mixed feelings about. Johnny started the career of almost every comedian performing in the 80s. He would invite the new comics on the scene to do their "tight 5" toward the end of the show. It was a poorly kept secret that if he invited them to "the couch" for an interview, they were in. He was christening them a comedy star. Robin Williams, Ellen DeGeneres, Louie Anderson, Roseanne Barr, Jay Leno, David Letterman, Steven Wright, David Brenner, Drew Carey, Garry Shandling, Eddie Murphy.

And we can't forget Yakov Smirnoff.

Johnny was basically the all-powerful comedy judge. It was seen as a huge honor to be invited to the couch. But if you had a bad night or a bad audience or just weren't ready, that could end or set back your career in a huge way.

You either got a sitcom or a job at McDonald's.

Jay Leno

Jay was known as a very good road comedian. He was a very hard worker who would perform *anywhere* just to get experience. He performed at strip clubs and crappy hotel bars and those weird corporate events where you have to come up with jokes for vacuum salesman or mortgage analysts. You have to use hyperspecific industry terms and include employees in the audience. John Mulaney recently made the news for one of these gigs.

Actually, let me give corporate comedy writing a try...

"Vacuum salesmen are the only ones who can start their pitch with how much their product sucks.

Suction, am I right, fellas? Good suction sells itself. Bob's wife knows what I'm talking about. She can hit 20 kPa, easy. Heyoooo!

She's still no Miele C3 canister vacuum with included HEPA filtration. That thing has more new attachments than the CEO's hair.

Your plugs aren't fooling anyone, Steve!"

Though Jay started out working mostly clean, so I'm not sure he would have rated the suction of Bob's wife in kilopascals. Working clean meant he could do his act just about anywhere. But don't confuse him with a "clean" comedian.

Froggie Comedy Tangent

A comedian who happens to work clean can be funny. But a "clean comedian" will make you wonder how you are suddenly in Branson sitting next to a youth pastor and his flock. If they specifically brand themselves as "clean," you're just going to get thinly veiled (or blatant) conservative comedy. It will technically be apolitical, but all the subtext is MAGA.

I call it "I remember that" comedy. Because every laugh is derived from "Hey, that's that thing I know! I remember that!"

There is a thing called "Dry Bar Comedy" and their entire deal is inviting clean comedians to do shows. The non-drunk audiences (Get it? DRY bar) are laughing their heads off and it is so confusing.

I keep going "Wait, when did he tell a joke?"

They don't have to tell jokes!

They just have to talk about the "good old days" and people will be like, "I remember Cabbage Patch Kids!" and laugh at something resembling a punchline. Or sometimes there isn't a punchline—just a declarative statement that sort of goes up at the end.

I could have a lucrative comedy career just saying things like, "Do you remember G.I. Joe? I sure do miss when toys didn't have pronouns."

*uproarious laughter*

Almost every comedian that performs at the Dry Bar has a bit about spanking and ADHD.

"Kids these days have it easy. If you talk back to your daddy, you get a time out. Can you believe that? When I talked back to my dad, he made me pick out my own switch!"

*uproarious laughter*

"We didn't have ADD back then. We just had misbehaving children and a belt."

*uproarious laughter*

Comedians like Jerry Seinfeld and Jay Leno worked clean but it wasn't a moral thing. It just wasn't necessary for their material and was more marketable for gigs. They told real jokes with a premise and a punchline. They did the work and earned their laughs.

END OF TANGENT

It's weird to think Jay was once a respected and talented stand-up. Looking back, his material was... jokes for your dad. That's the best I can describe it. Not dad jokes, but jokes dads liked. Clever observations that would make dads go, "It do be like that!" Not really my thing, but he was good at it and he still draws decent crowds to this day. I mean, they all need walkers to get into the theater, but he packs the place with geriatrics wanting to laugh at Monica Lewinsky and OJ Simpson like the old days. Spoiler, Monica was a slut and Jay thinks OJ did it.

Jay did an adequate job on The Tonight Show. He was an okay interviewer and guests felt safe going on. They knew he wasn't going to talk about anything too embarrassing (with one major exception being Hugh Grant after he was caught with a sex worker).

Jay relied on bits that he knew worked and never really strayed once he had a working formula. He would read funny headlines. He would do his "Jaywalking" remotes where he found stupid people and used deceptive editing to make it seem like everyone he talked to was that stupid. Jay is really into things showing the decline of America in relation to the WWII generation.

Jay was the status quo comedian. He never really had "moments" that stood out and became legendary. Johnny had an entire DVD business just selling old clips from his Tonight Show. They were filled with moments that were so spontaneously and authentically hilarious that they stood the test of time. But trying to find a "greatest hits" compilation of Jay Leno's run will just leave you bored.

If you search YouTube for Jay's best moments, you just get a bunch of his "Headlines" segments. He's literally just reading clips from the newspaper.

As I mentioned in my other post, when he isn't in comedian mode, Jay Leno seems like a decent guy. He treated his staff very well and his work as a car historian is near academic level. When you hear him talk about old cars you feel like you are spending a weekend with your grandpa. So Jay's mean spirited monologues just seemed out of place and I think looking back, they ruined any chance he had at a legacy.

He just took cheap shots at celebrities and politicians and people in the news. And he did it relentlessly whether people deserved it or not.

Yes, every host at the time did this. But Dave felt like he was going through the motions and doing the monologue just because it was part of the format. His heart wasn't in it and he much preferred bantering with Paul Schaffer in the band than telling jokes about celebrities he doesn't actually care about. He was more interested in getting to the desk and doing his "real" comedy.

And Conan's jokes about celebrities were more silly than mean. He'd make fun of Tom Cruise or someone and then do the string dance.

But Jay would go dark. He had a smile on his face and it sounded like he was "just joking" but after hearing about Monica Lewinsky's story, Jay Leno's "just joking" was different. I remember Jay Leno making fun of that poor woman who had McDonald's coffee burn her vagina off. He probably got a few months of jokes out of that. He was such a nice guy outside of his comedy and looking back it seemed so out of place. But I think he did cheap shots because it was an easy laugh and he figured the famous weren't "real people."

If Jay was in head-to-toe denim, he was a solid dude.

If he was in a suit, he was an asshole.

Jay never stopped doing stand-up. You can catch a show this weekend if you want. Jay really likes to pepper in some classic 90s jokes about celebrities we have mostly forgotten. As I mentioned in my other post, I've heard him do Monica Lewinsky jokes as recent as 2019. They aren't part of his written material. They are usually ad-libs and callbacks. Like if Jay was fixing a car and someone said, "We need to suck the air out of these tires." There is a 90% chance Jay would respond, "Boy, where's Monica when you need her?"

He still does the "jokes your dad would like" material in his personal act. But they are much more like his Tonight Show monologues than his old stand-up. Easy jokes without much thought. Instead of his classic clever observations, he mostly complains about modernity, ad nauseam.

Actual joke...

"Have you seen these phones on your wrist? And you thought BUTT DIALING was bad!"

Get it? He's saying people are masturbating and accidentally calling people. Which completely misunderstands... no one talks on the phone, Jay. It's 2025 and we all have anxiety. Maybe you could do wank texting?

Okay, Jay. How about this as a joke, complete with a 90s reference...

"Have you seen these people wearing phones on their wrists? I guess they finally solved butt dialing!

But after they see a sexy picture of Cindy Crawford, Apple tells them they have 30,000 steps for the day!"

A famous fun fact is that he never spent any of his Tonight Show money. He lives off the interest and income doing stand-up. While he was host of The Tonight Show he still did stand-up just about every weekend. *I* think that *he* thinks that gives him working class cred despite his enormous wealth and caravan of supercars.

I'm glad his money allowed him to become the world's greatest car historian. I'm happy there is someone like him doing proper car conservation. His restoration of the Chrysler turbine car was fantastic. That is a neat piece of engineering and car history.

Jay never had a sex scandal and seems to love his wife. He's taking care of her as she battles dementia. I do feel sorry he is going through that.

Those are the nice things I can say about him.

But I think Monica Lewinsky and Conan O'Brien should be allowed one giant kick in the nuts.

David Letterman

Conan O'Brien wasn't the first person Jay Leno screwed over with The Tonight Show. David Letterman was actually Johnny Carson's favorite guest host. But he was quirky and experimental. The network liked Jay Leno's safer style.

It was a big controversy at the time and they even made a weird movie about it called The Late Shift. Pretty much every person portrayed claims it is horribly inaccurate. The actors they cast looked like when you draw from memory.

The big joke at the time was about the ridiculous chin prosthetic. Did you know Jay has a sizeable chin? Let's get Stan Winston away from Terminator 2 to make this bigass chin.

Dave started out as a TV weatherman. But once he got popular doing stand-up, they gave him a morning show. They tried to make him Regis Philbin. But he sucked at being Regis. Only Regis could be that excitable in the morning. Dave wasn't really a "morning" comedy guy so that was quickly cancelled.

In 1982, he got the Late Night show at 12:30am after Carson on NBC. No one paid much attention to him and he realized that. I think that excited him and he was just like...

Dave and his team created some of the most experimental comedy on broadcast TV up until that point. He was basically unsupervised in a comedy laboratory for over a decade.

He wore an Alka Seltzer suit and dunked himself in water.

He wore a Velcro suit and hurled himself against a wall.

Looking back I'm realizing he did a lot of suit based humor.

He had a very long running gag with character actor Calvert DeForest who Dave called Larry "Bud" Melman. He was a bit like a sidekick.

Calvert was this cute old man and would literally do *anything* Dave and the writers asked. He had no fear. He had no shame. He would often go to random places and interview people. But he was really bad at following the scripted material and would get confused and forget the jokes. He didn't understand how microphones worked. Any segment with him would go off the rails because he never quite understood the premise. Dave loved this tiny, elderly ball of chaos. The trainwreck was the joke.

Dave helped Super Dave Osbourne get his incompetent daredevil schtick out there. He let Andy Kaufman get in a fight with someone and no one could tell if it was a bit. (10:30)

Johnny and Jay's Tonight Show was where all the normie comedians went to get their big break. Dave was where the weirdos flocked to. And some of them were terrible, but they were *always* fascinating. I don't think Frank Zappa would have his cult following without Dave.

Dave was the first to regularly do "remote" humor where he'd just go out into the world and get into trouble with real people. The segments were great but Dave struggled with social anxiety. So that eventually evolved into Dave hiding in a van and making a Chinese-American deli owner named Rupert Jee repeat awkward things said in a hidden earpiece.

Dave's interview style was erratic. He was a very good host as long as he liked his guest. He loved having a real conversation with a fascinating person. He rivaled Craig Ferguson when those conditions were present. But if he didn't care for them, things would either get very awkward or very boring.

He didn't like pop celebrities who didn't have genuine talent. Paris Hilton or Kim Kardashian would have driven him nuts and he would purposely seem bored when interviewing someone like that. Dave had trouble "faking it." And instead of Jimmy Fallon's cringe fake laughter, Dave would just appear utterly uninterested.

But if he didn't like someone and chose awkward over boring... hoo boy... it was *really* awkward. And Dave relished in the discomfort.

Madonna (who Dave acknowledged as genuinely talented) was unhappy about his monologue jokes. Essentially he alluded to her being a bit of a slut. It was typical Late Night comedy fodder at the time. I'm not endorsing it, I'm just saying everyone did it and society didn't have a problem with it at the time. She released a book about sex called... "Sex." Then she released an artistic softcore black and white erotic music video that most people felt was... more strange than sexy. She just kinda talk-singed to the same loop and made out with a dude while clips of a dancer in full body spandex came out of nowhere.

The Wayne's World parody was much better and somehow less weird.

Needless to say, people made fun of this pivot to weird erotic art.

In any case, Dave had Madonna on and she turned the weird up to 11. I think she was trying to get back at Dave, but it had the opposite effect. He saw where things were going and he just kinda... "let her cook."

He was delighted to watch the train wreck unfold.

I mean, she was right. She was being slut shamed—by everyone, not just Dave. But she was so overtly odd that it was hard for people to hear that conversation within the chaos. And the only thing the mainstream news cared about was her potty mouth.

On the other hand, he liked Drew Barrymore a lot. Drew was a very good actress and she was charming and funny. She was just as weird as Madonna, but it was not oppressively weird.

I think Dave saw her more as a daughter figure. Or maybe he wanted to and was ashamed he wasn't successful? Or she made it difficult for him to be a father figure? Because she saw him as a... umm... daddy figure? He enjoyed her company but was uncomfortable with her affection, so her interview was awkward in a different way. This was especially famous because she ended up flashing him for his birthday.

Dave was complicated. He was a former alcoholic. He suffered from social anxiety while having the world's most social job. He was the most private public figure you could imagine. He managed to have a sex scandal that no one seems to know about or talk about. He was involved with his personal assistant who regularly appeared on the show. Then her roommate tried to blackmail Dave for two million dollars by threatening to expose the affair. Dave decided to just fess up and helped the authorities with a sting operation to catch the extortionist.

Dave was self-conscious and neurotic. I don't think he liked himself for a very long time. Which is probably why he tried to blow up his life and family. But he loved his son and once that love took hold he seemed to get his shit together. He seemed like a different person. I liked Dave's comedy much more when his life was a hot mess. But I liked Dave as a person much more when he started choosing good behaviors. Much like Jimmy Kimmel, family seemed to make him a better person.

Dave pushed the late night format to the limit and inspired an entire generation of comedians. He encouraged them to try risky things and experiment and became the comedy mentor that Jay Leno wishes he was.

Also he loved his mom and sent her to the Olympics and it was the cutest thing ever.

I'm a sucker for people who love their moms.

Conan O'Brien

Conan was my comedy idol. If you have followed my comedy over the years, you might have noticed a similar embrace of... intelligent silliness.

Stupid smart?

He was a magna cum laude Harvard graduate and a clown without the makeup. He was originally a comedy writer and head of the famous Harvard Lampoon humor magazine. He went on to write for The Simpsons and SNL.

He wrote that monorail episode.

Every Conan fan who wants to share a fun fact will make sure you know he wrote the monorail episode. Kumail Nanjiani did a great bit about this during Conan's Mark Twain Prize ceremony (it's on Netflix).

After Jay took over The Tonight Show and Dave gave NBC the finger and left for CBS, the "Late Night" slot needed a new host. And Lorne Michaels decided this pale redheaded giant from the SNL writing staff might be a good choice. No one had any clue who he was. No one had any confidence in his success—including Conan.

And the only person who saw a spark of genius was... David Letterman. (2:20)

Conan just started cranking out as much weird comedy as he could. The Masturbating Bear, Pimpbot 5000, FedEx Pope. There was a pooping robot at some point.

They had a sizeable robot budget.

He was the true spiritual successor to Dave's 80s Late Night show. By this time Dave mellowed out and didn't have the motivation and hunger to innovate like he used to. So Conan filled that role.

I think the reason Conan appealed to me specifically was because I saw a lot of myself in him. I was good at a lot of different styles of comedy—I had this almost shapeshifting ability to customize my humor to the person or audience I was entertaining. But eventually I decided I just wanted to make people feel good. I had to pick a style and stick with it. I wanted to make comedy comfort food that wasn't dumbed down or patronizing. It could be stupid and corny but I didn't want my audience to feel like they were stupid for liking it.

I don't know if I'm making any sense.

Conan was a genuinely nice guy and a constant people pleaser. He didn't have an edge and he didn't need one. He could do innovative comedy without punching down, without trying to push any offensive lines, without saying fucked up shit just to see if he could get away with it.

I'm not even knocking comedians who are skilled at dancing on the line. Some of my favorites of all time played with the line. Lenny Bruce, Richard Pryor, George Carlin, Chris Rock.

Louis CK and Dave Chappelle before they...

*heavy sigh*

But so many comedians at the time thought that was an easy path to success. They didn't realize you had to be incredibly funny in order to stand next to or jump over the line. You had to compensate with amazing jokes to get away with it. But that takes effort and talent and finesse. They preferred laziness and brute forcing edgelord material.

And that is how we got a gaggle of Joe Rogans.

Hmm, we need a better collective noun.

That is how we got an ivermectin of Joe Rogans.

Conan was unapologetically silly. But it had this foundation of intelligence in the subtext. And every once in a while, he'd let an Abe Lincoln fun fact slip out (he could be a legit Lincoln historian if he wanted to). He made comedy for smart people who needed to turn down the volume of their brain for a bit.

Thinking is exhausting sometimes, but you can't shut it off completely.

Conan struggled for several years to find an audience. I think he was on the verge of cancellation every few weeks. I watched him every night from the first show. I started to see what Letterman saw. It was really neat to watch him learn and grow. He taught me that comedy was a journey. And eventually people found him and loved him and the rest is history.

My favorite running gag was definitely the Walker Texas Ranger lever. He'd randomly pull a big red lever and all it did was play a clip from the show. Everyone knows the Haley Joel Osment AIDS clip, but that was not my favorite. (2:40)

Walker was an egalitarian karate pugilist.

It was such a brilliant bit that relied on Conan's setup and reaction. If he just played the clip without the antics, it would not hit as hard. It would be Jay Leno reading the newspaper.

And... I don't have the energy to fully explain Jordan Schlansky.

I wouldn't even know where to start.

The short version is... Conan doesn't quite know how to handle intense nerdy metrosexual autism and hilarity ensues.

I encourage you to go down the Jordan Schlansky rabbit hole. I promise you will start watching and suddenly it will be tomorrow and you'll look at the clock and not be sure if it is AM or PM. If you are wondering, yes, he is really like that. But he pretends not to be self aware to make it funnier.

And then there is Sona. Conan's Armenian assistant who doesn't do a lot of assisting. They are basically siblings. You can tell she became part of his emotional support system. At times she matched Conan's comedic brilliance without any experience or training. She has perfect timing and can hilariously devastate his self esteem like an emotional assassin. (2:45)

There is so much more, but you get the idea.

Conan is a brilliant, silly comedian. And he is a solid dude. Just like Leno, his staff stuck with him. He was a great boss that inspired fierce loyalty. They even moved from New York to Los Angeles for him. And when he lost The Tonight Show he started his own company just so he could keep everyone employed and paid. That eventually evolved into his successful Team Coco podcast network.

Before his TBS show, Conan was contractually obligated to not appear on television for a year. He went on a grueling tour across the country performing a live comedy musical variety show. This was mostly to maintain his staff until they could find a new TV home.

They made a documentary "Conan O'Brien Can't Stop" about this live variety show. Some people thought this revealed Conan to be a bit of a dick. But he just lost his dream job, his entire staff had no source of income, and he was going from city to city working 18 hour days, including a 2 hour, high energy stage show—all while trying to stave off his deep depression. (Also Jack McBrayer was an old friend, and that was an ongoing bit between them.)

I don't think I've seen Conan that vulnerable and that human and you could see his staff doing their best to keep him from imploding. He felt responsible for the livelihoods of hundreds of people. They loved him and knew he was doing it for them.

(And because he needs constant attention and validation, but what comedian doesn't?)

To end things I think I'd like to try one of my comedy exercises.

I'm going to do a Top 7½ list in the style of David Letterman Bob the Frog. I can only promise junior high level comedy.

(Also, if you have never seen Dave do one of these, number 1 always has a drumroll and is purposely bad.)

Top 7½ signs you are in a "clean" comedy club.

7½. The headlining comedian was cancelled for...

7. You ask for the drink specials and the waitress says they might have Diet Sprite in the back.

6. The comic was once ratio'd on Twitter after being called "Temu Jeff Foxworthy."

5. "Back in my day we had Transformers not transgenders. The Autobots' pronouns were roll/out."

4. The comic takes off his belt, holds it up to the crowd and says, "This was what we called Ritalin in the 80s."

3. Your seat has a gun holster next to the cup holder.

2. The comic assures everyone that he "found God" so there is no reason to google his name and "me too."

*drumroll*

Annnnd, the number 1 sign you may be in a clean comedy club is...

1. Thursday is "Free Tennis Balls for Your Walker Night!"