Elon Musk is dying to be funny. These comedians have notes

You’d think Elon Musk, the second-wealthiest person in the world, would have bigger worries than whether or not strangers on the internet find him funny.

Yet despite the long list of business concerns demanding his attention — making self-driving cars, launching reusable rockets, implanting microchips in monkeys’ brains and, as of last fall, running Twitter — Musk seems desperate to add “comedian” to his portfolio.

The billionaire has hosted “Saturday Night Live” and guest starred on “The Simpsons.” He once considered buying The Onion, then ended up funding a short-lived competitor instead. He’s reportedly tried to cultivate relationships with cringe comedian Nathan Fielder and the creators behind “Rick and Morty.”

Online, he has a reputation for interpolating corporate PR with nerdy puns and — in his words — “dank” memes.

“Comedy is now legal on Twitter,” he posted after acquiring the platform, signaling a jokes-first ethos that’s since been undercut by his crackdown on parody accounts and beefs with Kathy Griffin, The Onion and the absurd humorist @dril (not to mention an increasingly uninhibited embrace of the far right).

“I think I’m funny,” Musk has said — under oath, no less. Perjury? Rolling Stone recently summed up his output as “garbled gags, corny jokes and pilfered memes.” Comparing him to “The Office’s” Michael Scott, the New York Times deemed him “the boss who thinks he’s funny but isn’t.” An individual claiming to have auditioned to run Tesla’s social media presence diagnosed the car company’s chief executive with a “soul-deep inability to post.”

In the spirit of helping Musk realize his comedic aspirations, The Times assembled a crack team of stand-ups, comedy writers and all-around funny tweeters. We asked these experts, whose credits include “Last Week Tonight,” “Bob’s Burgers” and “Community,” to review Musk’s humor output and offer the kind of no-holds-barred notes they might give in a tough but caring writers’ room.

Spoiler: They didn’t think all of his jokes were completely bad — but it’s safe to say he’s got a lot of work to do on his tight five.

Interviews with participating comedians were conducted over Zoom, email or via a Google form. Answers have been lightly edited for clarity and brevity.

‘That’s what she said’

Every adolescent boy and fan of “The Office” knows the proper response to an unintentional sexual double entendre: “That’s what she said.” It’s not exactly high-concept. Yet Musk’s recent attempt to use it was more confusing than anything.

In March, Rep. Hakeem Jeffries tweeted: “House Dems are fighting hard for the American people. Right-wing extremists are fighting each other.”

Musk replied with an attempt at innuendo … maybe?

Hari Kondabolu, stand-up comedian and creator of “The Problem with Apu”: The problem is “fighting hard” does not have a double meaning. Also, a second sentence preceded his “joke,” so it’s not really clear what he was trying to do.

Jiaoying Summers, stand-up comedian and owner of the Hollywood Comedy: He didn’t use it correctly. There is nothing sexy about it.

Spencer Crittenden, “That Happens” podcaster and writer: What if he’d said, “Check, please”? It’s just as stupid, just as nonsensical, but it just fits a little bit better, right? … There’s just a little bit more of a twinkle in your eye about it.

Laurie Kilmartin, stand-up comedian, podcaster and former “Conan” writer: The more I think about it, the less sense it makes. This is the kind of comedy that AI writes, and this is what you can expect if the AMPTP does not meet the demands of the WGA.

The sex number and the weed number

A bit of internet culture, for the uninitiated: The number 69 is the name of a sexual position, and 420 is a reference to smoking marijuana. To a certain segment of the online public, the mere mention of either number is understood as a humorous act.

Musk makes a lot of 69 and 420 jokes. A lot. A few examples: He recently updated the Canadian Broadcasting Corp.’s Twitter account to say that it’s 69% government-funded; set 4/20 as the date for eliminating legacy blue checkmarks and launching the giant Starship rocket; and once priced the Tesla Model S at $69,420. (Notably, after getting sued over it, he also testified in court that a tweet saying he was going to take Tesla private at $420 was not a joke.)

Crittenden: What’s funny is that he keeps stepping on rakes because he needs to do 420 jokes. It’s destroying everything. I mean, the reason that the rocket exploded [is] because he committed to a 4/20 launch date as a joke. It’s insane! Thousands of birds died because of a 420 joke.

Comedian Laurie Kilmartin stands on stage with a microphone

“I prefer boob jokes to retweeting white supremacists.” — Laurie Kilmartin

(Mindy Tucker)

Kilmartin: In this year of our Lord 2023, 420 jokes can be funny if the person acknowledges how hacky they are. Elon seems to think they’re funny on their own, which is embarrassing. Personally, I love a good “noice” after any number that is or contains 69 but “69” itself is not a real punchline.

Nikki Glaser, stand-up comedian and host of “FBoy Island”: This is legitimately hilarious because it’s so stupid. The best joke is that he thinks he’s clever. He’s Michael Scott meets Dr. Evil.

Kondabolu: In order for a 420 joke to be funny at this point in human history, the audience must all be high. To make a 69 joke work, you must be in a locker room with straight men who are telling such jokes to ease their discomfort in a clearly homoerotic situation.

George Chen, stand-up comic and host of “Talkies”: His most successful numerical-naming joke was “X Æ A-X12” [the name of Musk’s child with the musician Grimes].

‘Let that sink in’

Last October, after he finally completed his acquisition of Twitter, Musk brought a well-known meme to life: He walked into the company’s San Francisco headquarters carrying a full-size sink, then posted a video of the stunt captioned “Entering Twitter HQ — let that sink in!”

Glaser: I feel so bad for the person he made run to Lowe’s for this joke and for all the people in the room with him when he came up with it who had to fake laugh.

Comedian Nikki Glaser poses with a microphone

“The best joke is that he thinks he’s clever.” — Nikki Glaser

(Courtesy of Nikki Glaser)

Summers: That’s a perfect metaphor that he is letting Twitter go down the drain.

Crittenden: Imagine that tweet — he’s walking in, video, carrying a sink — and it just says, “Entering Twitter HQ.” That’s funny! It’s just — it’s funny. Because why is he carrying a sink? It’s stupid. It’s funny. … But him going, “Here’s my bit, here’s my prop, I’m Carrot Top, execute, slam dunk, here’s the punchline”? It’s like, no, let the picture be the punchline.

Kondabolu: What worked about the joke is that I was able to realize it was an attempt at humor and then was able to connect the picture with the text. What did not work was its ability to make people laugh or minimally feel good that this “joke” existed in the world.

Kilmartin: Carrying an actual sink into an office building was so weird that most people’s first reaction was “huh?” not “haha.”

Josh Gondelman, writer, “Desus & Mero” and “Last Week Tonight”: It’s extremely sweaty, meaning it’s a LOT of effort for a very low yield. He took a literal long walk to the punchline.

‘Pedo guy’

Was Musk trying to be funny when he notoriously called a cave diver who had criticized him a “pedo guy”?

Probably not, considering that he subsequently attempted to convince a reporter that the man, Vernon Unsworth, was in fact a “child rapist.” But, faced with a hefty defamation suit, Musk attempted to shield himself by claiming it was a joke. OK, sure. But was it a good one?

Gondelman: To me, a handy rule of thumb is that if you need a lawyer to say, “Your honor … he was kidding,” then the joke didn’t land.

Glaser: Calling a grown man who eagerly works with young boys a “pedo guy” is far from a good joke, but I would probably make this same “joke” if my fragile ego were wounded when a guy who worked closely with kids made fun of my asinine idea to rescue said children with a tiny submarine. However, I wouldn’t tweet it; I would maybe just say it to my friends, but who knows if Elon even has those.

A black and white portrait of comedian Spencer Crittenden

“It’s like an alien’s version of comedy.” — Spencer Crittenden

(Steve Agee)

Crittenden: Comedy is about expectations, and expectations are about understanding how people normally think. I think this is the breakdown where Elon Musk’s comedy usually happens.

Kilmartin: It’s not a joke, it’s a nickname, AND it’s a nickname I’d give any man who had their photo taken with Ghislaine Maxwell.

Chen: I guess you had to be there?

Kondabolu: I think he has confused “a punchline” with “slander.”

Andy Kindler, stand-up comedian and actor, “Bob’s Burgers”: One of the keys to comedy is self-deprecation. The great Richard Lewis will punctuate a joke by saying something like: “But what do I know? I’m dressed like Satan at a barbecue.” Similarly you could say: “But what do I know? I’m the despicable asshole who smeared Paul Pelosi.”

Tweets from the ‘Chief Twit’

Most of Musk’s stabs at being funny take the form of tweets. Often, the puns or memes he tweets are lifted from another account without attribution, but now and then he’ll get off an original one. Some notable efforts:

Crittenden: It’s not a punchline. It’s just conservative buzzwords.

Glaser: I first heard this Evian joke/observation at recess in 1997, so he did not write that.

Kondabolu: Evian joke is amusing as it’s a commentary on bottled water with a mildly interesting observation.

Crittenden: This is not a joke. It’s literally — this is a statement of fact.

Chen: It has the ring of truth to it. However, I think I’ve heard that one elsewhere, so — parallel thinking? I do like the pun for the Boring Company [Musk’s tunnel-digging startup] so it’s not me blindly hating.

A portrait of comedian Hari Kondabolu

“Real comics are generally broke.” — Hari Kondabolu

(Rob Holysz)

Crittenden: Stolen joke, made worse…. [John] Mulaney just did a stand-up act, and he has a very good version of this bit. It’s about cocaine and selling watches. The concept itself is funny, but it’s about the execution. … It feels like a very safe, market-tested form of vulnerability.

Kondabolu: Might be funny to me if he wrote “Start with Dad’s large fortune.”

Glaser: The Jack in the Box one is legit funny, but I would bet $420.69 he did not write it. The other ones he most certainly wrote because they are not funny.

Kondabolu: It would be stronger if he said “Jack in the Box bathroom.”

Kilmartin: I’m sure these lines got a lot of laughing emojis on Facebook, and I’m happy for the twice-divorced uncles who enjoyed them.

File under: Breasts

Musk recently painted over the ‘w’ in the Twitter headquarters sign so it read “Titter.” Before that, he joked about wanting to found a university called the “Texas Institute of Technology & Science,” or TITS. (“Universally admired,” he self-replied.)

Glaser: He has the sense of humor of a seventh-grade boy or a horny dentist.

A headshot of stand-up comedian George Chen

“I guess you had to be there?” — George Chen

(Jaime Borschuk)

Crittenden: “Tits” isn’t funny. “Funbags” is funny. “Boobs” is funnier than “tits.” Like, there’s a lot of — “rocket dogs.” “Chesticles.” If you want to find the comedy in breasts, it’s there.

Summers: These are bad boobs jokes! They are like the fake tits in the ‘80s.

Chen: Boobs are low hanging fruit but even lower hanging fruit is Texas Eastern Science & Technology Education School (TESTES).

Kilmartin: I prefer boob jokes to retweeting white supremacists, so let’s keep pointing him in that direction.

File under: Testicles

In another recent bit of wordplay, Musk changed his Twitter handle to “Harry Bōlz.”

Kilmartin: I’m too distracted by the misspelling of balz/balls. What’s that “ō” doing there, unless that’s a South African thing? Every joke he attempts is a tiny bit off.

Crittenden: “Bōlz” is not a good way to spell it. It’s not funny. ‘“Harry Bōlz” is just nothing. Balls are just hairy. It’s just what they are. … It feels like someone trying to fake what humanity is. It’s just very weird. It’s like an alien’s version of comedy.

Summers: None of these jokes are verified. You can buy a blue checkmark but you can’t buy Louis CK’s red carpet. Elon is not welcome in the Comedy Store.

Kondabolu: Clearly plagiarized from a seventh grader.

It spells ‘sexy.’ Get it?

It’s no accident that the model names of Tesla’s cars — S, 3, X and Y — spell the word “sexy,” kind of. That was Musk’s intent, partially thwarted by a lawsuit from Ford that forced him to settle for “3” over “E.”

Summers: It reminds me of when kids would spell 80085 on a calculator as BOOBS. When you are a multibillionaire, you can spell it with Teslas. It’s like a failed dad joke from someone who never had a father figure.

Crittenden: If it was initially conceived as that, I think that’s a little funny. But then that’s too try-hard, right? It’s like, “Oh, my entire production line of cars is in service of this joke.” They aren’t good car names. So if that was the idea, that again becomes very unfunny — and also sad.

Chen: Excellent use of the comedy “rule of 3s.”

Glaser: This is clever, but it’s neither funny nor sexy. I wonder how many times a day he says, “Get it?”

Just throw money

Handling audience hecklers is a key part of every comedian’s skill set — one that Musk could have used during a surprise onstage appearance at a Dave Chappelle show last year. He reportedly made a joke about living in a simulation and quoted a line from “Chappelle’s Show” — “I’m rich, bitch” — but for the most part just kept getting booed by the crowd. “Dave, what should I say?” he asked at one point.

Kondabolu: He should have started throwing money at the crowd. People like money.

A portrait of comedian Andy Kindler

“There’s nothing funny about greedy crony capitalists.” — Andy Kindler

(Susan Maljan)

Kindler: Don’t mention the fact that you’re wealthy. Everyone hates the rich. The only reason why people care about you is they think you’ll pick up a check or put their children through college.

Summers: Never brag about yourself to the audience, it’s super unfunny and unattractive. There is only one thing Musk could have done to get the crowd on his side: give everyone in the audience a free Tesla, free stem cell therapies and an Elon embryo with a trust fund!

Chen: I think standing there saying nothing and letting your friend Dave Chappelle shield you from the boos is exactly how we would want this to go.

Closing notes

A picture of comedy writer Josh Gondelman

“If you need a lawyer to say, ‘Your honor … he was kidding,’ then the joke didn’t land.” — Josh Gondelman

(Mindy Tucker)

Glaser: The sad part is that he thinks he’s funny, but that’s really our fault more than his. We both fear him and also desire his wealth and power so in order to gain his acceptance, people around him laugh and encourage this. It’s the same as when people laugh at your pilot’s dumb puns. We laugh not because he’s funny but because we fear if we don’t he’ll fly us into a mountain.

Crittenden: It’s hard to be funny and cool. You have to be able to laugh at yourself, which is just a skill he doesn’t have. … If you just were as obviously broken as you clearly are, people would like it more just because people root for an underdog. But that requires a level of vulnerability that he’s not comfortable with.

Summers: Elon has enough money to hire Chris Rock and Dave Chappelle to put him in a crash course of joke writing and open mic training so he can actually get better and make people laugh genuinely. Or he can come to the Hollywood Comedy on Melrose to do their daily open mics. Please make the check out to Jiaoying Summers. She will yell at Elon for free.

Kindler: There’s nothing funny about greedy crony capitalists. People root for the underdog. David was funnier than Goliath. Jews in general are funny. Try hanging around some Jews instead of amplifying antisemitic tropes about George Soros.

Chen: If anyone could train an AI language model to replicate his tweet style and save a ton of time, it’s him. If he can put that AI language model into a robot vessel and send it to open mics, it would also be able to iterate at a much faster learning curve than a human comedian and potentially make all comedy writing obsolete.

Kondabolu: Real comics are generally broke, and struggle helps give you a relatable and interesting perspective. So he should just give me all his money.

Gondelman: Don’t quit your day job for comedy. Quit it for other, unrelated reasons.

Kilmartin: You have made me think too much about Elon Musk’s comedic sensibilities and I hate you.

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