PRO STANDUP COMEDY TIP: If you have a bit that gets laughs and has multiple punchlines that work, and you can’t think of a good way to end it, congratulations! That’s now your closer. Because if you end your set with “Thank you very much goodnight!” you’re technically closing on an applause break.

Remember, it’s almost never about the art, and it’s rarely about the craft. It’s about making it through the entire 45 minute set so that you can get offstage and get paid.

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ON LOVING DIFFICULT HEROES

I once belonged to a “Bob Dylan Fantasy Pool.” Since he was, for a long time, known for drastically changing up his set list from show to show when on tour, every single song was assigned a point value and before each leg of his Never Ending Tour players would put together song lists they believed he would play in concert.

I usually did pretty well, often ending in the top ten. While it is the definition of “true nerd shit,” this was the early 2000s when the Internet felt more like a fun place for dorks than a millstone we are all chained to through social media. As a result, the Fantasy Pool was written up all over the place and the founder, a nice Canadian programmer named Arthur, was interviewed on CNN.

My point is that I’m partial to pretty much anything Bob Dylan does, so it may come as no surprise that I enjoyed his recent book, The Philosophy of Modern Song. It’s a book of essays about his favorite songs, a master songwriter who just wants to share his passion for the music that shaped him as an artist. It inspires me to revisit some work by people like Little Richard and Hank Williams that were such a part of the background of my childhood that I tend to take their brilliance for granted.

So I think a semi-regular feature on this Substack going forward is going to be an occasional look at bits I like, the ones I grew up listening to or that deepened my love of standup as I grew older. There will be the usual Greatest of All Time candidates, as well as a few people you may have never heard of.

Not that I’m the Bob Dylan of comedy by any stretch of the imagination, but it’s something I’ve performed and studied since I was a teenager, and I do have a breadth and depth of knowledge about the craft that I’m eager to share.

However, that leaves an elephant that is not only in the room, but has grown impatient with waiting to be addressed and so has sat on all of the furniture destroying the couches and chairs, and also flipped through the record collection breaking each and every disc. And it is this:

A lot of the greatest comedians have also been tremendous creeps. And while most keep it to themselves, with the occasional Eddie Murphy late night “I was just giving her a ride home” arrest or a Richard Pryor documenting his depravity and turning it into high art.

And then there’s Woody Allen and Bill Cosby.

With Bill Cosby, the cosmic joke is that The Great and All-Powerful Cos was almost universally beloved and admired as one of the greatest comedians of all time and was also revealed to have been probably the field’s greatest monster.

Now, I’ve known for a long time I’ve known Cosby was not a good dude. In the 1970s, my mother was on a street corner in Greenwich Village and saw a fan approach Cosby outside the old Village Gate on Bleecker, asking for an autograph. The Cos took a cigar out of his mouth long enough to tell the man to fuck himself.

However, it was shocking when Cosby was credibly accused by hundreds of women of drugging and raping them. Not only was Cosby an evil man, but I felt slightly implicated. After all, this was the man whose concert film, Himself, my parents taped off of HBO and that we watched as a family multiple times. Various punchlines from the show – “Eggs! And milk! In the chocolate cake!” – became part of the regular patois in my family, ofttimes as shorthand for a thought or feeling that we shared and that Cosby had masterfully, perfectly, pinpointed and expressed in Himself.

And as the star of the The Cosby Show, many children of the 1980s saw Cosby’s Cliff Huxtable as the perfect father; loving, stern, goofy, protective. And Phylicia Rashad’s Claire wasn’t just his counterpart, she was his equal. We wanted to be part of that family. Bill Cosby was a role model for me. And to find out he wasn’t just not perfect, but unthinkably hideous. If I wanted to one day grow up to be Bill Cosby then who was I?

I’ll never write about Cosby or his act. It’s unfortunate that I’ll dump his standup down the memory hole. He has three bits that are the platonic ideal of the perfect standup comedy, an art form that’s important to me. Fuck him.

With Woody Allen, it goes even deeper. I didn’t want to be like Woody because I already fully identified with him. When I was ten I watched Bananas with my father for the first time, and my jaw dropped like a cartoon wolf in love. Here was a guy who was a fellow outer boroughs New Yorker, also extremely Jewy, certainly not the standard of male beauty in any culture. He was also a very famous and respected movie star and director, the funniest guy in the room onscreen and off, who in real life was dating his muse Mia Farrow.

And the man was an artist. While I don’t hold Annie Hall in the high esteem that many of my peers do, his run of 1980s films with Farrow – Purple Rose of Cairo, Broadway Danny Rose, Zelig, Hannah and Her Sisters – are masterpieces. When I was young I kept my dream of being a writer/director like Woody Allen to myself for the most part, because the truth was that where I grew up in Queens, saying you wanted to be a director was like saying you wanted to buy a vacation home on Mars. A fantastical dream at best.

There reached a point in my standup career when I knew that I had to either take it to the next level or quit. I’d done a mediocre set on Comedy Central, and then stalled out. It was reading a biography of Woody Allen by Eric Lax that underscored his insane work ethic, and made me realize that I had, up until that point, been phenomenally lazy in my own career, coasting on a natural charm and ability to come up with jokes onstage.

It occurred to me: I considered myself to be a professional standup comedian, and yet my act was mediocre and I didn’t know how to sit down and properly write an act. I wanted to be recognized for my genius and yet didn’t even want to do the hard work of being reasonably professional.

So I sat down and listened to a cassette of his double disc anthology Woody Allen: The Nightclub Years once a day for months. I studied how he constructed not just jokes but entire bits. He was a great place to start, because every one of his bits was a naked scaffolding on which to slot in punchlines. I’ll explain better when I write about “The Moose Joke” one day, but I listened to him and then wrote my ass off every day.

When I had a call center job, I wrote between phone calls. If I didn’t have a show at night, I’d go home and write jokes. I wrote a set list before every show, and afterwards I broke it down, joke by joke, punchline by punchline, noting what had worked and what hadn’t.

And because I knew how Woody structured his act, and I followed his template, I learned to slot punchlines in any space that had dead air. Eventually I learned how to let a bit breathe, but that’s another story.

When I got a chance to audition for Best Week Ever, a show where comedians commented on pop culture – like watching Twitter in real time but less angry – I had such a strong joke-writing discipline — the night before they’d email us all a packet of topics we were going to cover the night before, and I’d spend a minimum of 5 hours writing punchlines for each and every setup — that I got the job and got out of my call center helljob.

It’s no exaggeration to say that Woody Allen’s standup saved me in a very real way.

And yet. There are the molestation accusations. And there’s the matter of Soon-Yi, his then-partner Mia Farrow’s adopted daughter whom he married. I read Woody’s memoir last year, and while he gave a pretty convincing defense on the former, reading his side of the story on the latter made me go, “Yeah, he did that shit. And it was gnarly.” The way he broke the news to Farrow that he had engaged in a “love affair” with her very young teenage adopted daughter was by leaving a naked Polaroid of Soon-Yi in a place in Mia Farrow’s apartment where she would find it.

The truth is this. Whether you side with the Allen family or the Farrow family, there are human beings at the center of this mess. There is a young woman who, regardless of anything that did or did not happen to her, is clearly telling the truth as she knows it.

Whether you believe the Farrow family and their assertion that Woody committed an unspeakable act upon her, or you believe the Allen family and their assertion that Mia committed an unspeakable act in programming her child to believe that Woody had molested her, there still is a traumatized young woman whose life was destroyed - directly or less directly - by the actions of a selfish old man.

And so. This is my confession. As a human being I am appalled. As a comedian and a fan, I have forgiveness in my heart for him. I still watch his movies. I still enjoy his standup. It is what it is. So it goes.

I started reading a biography of Kurt Vonnegut, and I put it down almost immediately. I realized 15 pages in that I wanted to continue to love his books, which meant continuing only know about his flaws as filtered through his own writing.

Why do our heroes always, at some point, challenge us and make it difficult if not sometimes impossible to love them? Of every comedian I ever truly aspired to be growing up, the only two who have yet to let me down have been Mel Brooks and Bob Newhart. I hope nobody cashes in on a tell-all about these men when they cash out.

In the meantime, expect to read about the standup comedians I have loved in this Substack, dissecting their acts with you the way I’ve dissected them with myself.

This Substack remains free. If you wish to support my writing, please consider joining my Patreon linked below.

Sorry I Haven't Written in a While

On Loving Difficult Heroes