My 20 Favorite Stand-Up Comedians Of All The Times

I’ve been a fan of stand-up comedy since I was 15.  It’s all I gave a shit about in high school and my GPA reflected that.  Turns out that I really loved writing it more than performing it, and I’ve never stopped writing it. I’ve seen dozens of performances live, collected tapes and CD’s, and watched five million comedy specials since the late 80’s.  I have a list of my 20 favorite stand-up performers based on their careers on stage.  There’s no real order, but you can figure out who goes where.

 (Individuals have been left off of this list if they’ve been accused or convicted of sexual assault and/or converted to right-wing mouthpieces. Screw you guys.)

David Cross – I’ve decided that if I had made the leap to try and become a professional back in 1990, this is one of the guys I would have tried to suck up to. I would have failed.  Surly, sarcastic, brash, intelligent and a cantankerous asshole when he wants to be.  All the things I aspired to when I was 18.

Todd Barry – He actually writes and tells jokes.  He has a point of view but there aren’t a lot of traditional joke writers anymore and no one has his patient cadence. 

Richard Lewis – Retired, I think.  Back in the late 80’s and early 90’s, this geezer had an energy to his shows that were so fun.  Marc Maron said that they don’t have Jewish comedians like this anymore because they have medication for this type of frenetic anxiety and depression. Kind of a shame.

Maria Bamford – 100% original voice.  Absolutely one of a kind in every way possible. Open about her mental illness struggles and gives you a peek inside her chaotic brain.  I’ve taken all my kids to their first stand up show and this was my daughter Emily’s inaugural experience.

Randy and Jason Sklar – You know why this brother team is on the list? Because they’re fun.  They look like they are having fun up there and that’s a serious skill when you’ve been saying the same shit over and over.  Plus, they took a picture with me:

John Mulaney – Noob on the list. Unbelievable how gifted this guy is at such a young age.  Get in early.

Dave Chappelle – Speaking of being gifted at a young age.  I saw this guy on Comic Relief when he was 19 and he was already a seasoned pro.  He’s one of the few all-time titans who achieved his own voice, becoming a comedian and social commentator while remaining funny. 

Jim Gaffigan – Do you have any idea how difficult it is to remain a ‘clean’ comedian and stay funny for decades?  There is a select group of people who can suck the marrow out of any mundane premise and make it all gold.  Still haven’t seen him live. Tickets are too pricey.

Paula Poundstone – She is the first comedian I ever saw.  In a shitty club in Orlando, and she crushed. Her 80’s specials are engrained in my brain.

Dave Attell - The closest thing we ever got to a Gen-X Don Rickles.  Fast on his feet, dirty, and a pure joke writer.  I took my oldest son Nick to Attell for his first show.  He lost his mind.

Bob Goldthwait – Bobcat has 4 careers.  80’s stand-up star, lukewarm comedic actor, indie film director, modern club comic.  First major name I saw live and he clashed with the redneck audience that paid to see him.  Lifelong punk attitude and native of Syracuse, New York, like yours truly. Minus the punk attitude.

Andy Kindler – Honestly, sometimes this guy is number 1 on my list.  Truly.  Absolutely no one does what he does.  He deconstructs the actual stand up experience, the jokes, the audience, the other comedians.  It’s more performance art and it all comes out of the mouth of a cranky old man.  He is known as a comedian’s comedian, which means only funny people enjoy him.  Again, it’s a shame.

Ellen Degeneres – You read that right.  Don’t give a shit about her talk show or even her sitcom.  Ellen was one of the most remarkable stand-ups in the 1980’s.  Even better than a lot of her male counterparts. Having a voice is so key and it seems like she had it the whole time. If you have to separate into categories…greatest female stand-up ever.

Bill Hicks - I’m one of the few people who was actually a fan of this guy before he died of cancer in 1994. Had his albums on cassette. Part lonely political comic, part paranoid stoner.   Some of the stuff doesn’t age as well, and when I think of him, I wonder what he would have been like if he had time to grow. 

Dana Gould – Stalwart comedian who was also a writer for the funniest show of all time, The Simpsons. He comes from the first generation of nerds and weirdos and has also dipped his toe in political commentary. My son Holden’s first show.

Paul F. Tompkins – Belongs on the list because of a unique voice and confidence on stage.  I’ve enjoyed probably 1000 hours of his improv work in the last 10 years in podcast-land so it did color my opinion, too. An attitude of ‘if you don’t get it, that’s your problem’.  Love it.

Chris Rock - Now we’re hitting my Mount Rushmore.  There is only one successor to George Carlin, and it is Chris Rock.  A millionaire, yet still needs to get specials out there. He needs to still perform. There are at least one or two undeniable brilliant observations per stand-up set. There are jokes, but there are big ideas behind them. Sometimes he’s just talking to us, and that’s what makes him like Carlin. 

Patton Oswalt – Patton was created in a lab when I needed a comedian to speak directly to me.  I would have tried to befriend him too if I put myself out there in 1990 but he would have thought I was a hack and told me to fuck off. The godfather of nerds, social commentator, writer, father, husband, fat guy.  Seen him twice.  Will see him again.

Richard Pryor - I mean, come on.  The funniest comedian of all time.  Legend.  Hall of famer.  He helped define what a stand-up is and what he could get away with.  If you haven’t gone back and checked him out, pay attention to when he gets into story mode.  He breathed life into every character, each with a unique voice.  You’re listening to a story about eleven different people and Pryor is the voice they’re coming from. He also anthropomorphized animals and everyday objects. It was rhythmic; musical. It all started there.

George Carlin – Pryor is the funniest comedian of all time; Carlin is the best comedian of all time.  A machine of writing, observation, social commentary, wordplay, language study, fart jokes.  He could do everything.  (Except relationship stuff.  Ever notice that?  He skipped that shit.) Hours and hours over forty years.  Insane work ethic.  He also evolved over time.  Straight-laced club performer, hippie stoner comic, 70’s drugged-out waste, reinvigorated political commentator, grumpy old man, enlightened old man. His later stuff was aimed directly at Americans in general, whom he thought could have been so much better.  Some bristle at his later stuff that is ‘mean’ to the audience, but I think we need that.  I don’t think we’re ‘soft’, as much as we need to not take ourselves so damn seriously.

Another reason I’ve always loved comedy.