The Greatest Stand-Up of All Time

There’s an old joke that goes “dying is easy; comedy is hard.” Having tried (with mixed success at best) to do comedy on stage, on the printed page, and on the electronic screen, I can attest to this fact. The hardest of all is doing stand-up. When you do stand-up you’re putting yourself out there, in front of the audience, with no script, no character, nothing separating you from them except for the common decency and respect that we all have for each other as human beings… and they’re all a bunch of rowdy drunks looking for a good time, and they don’t care if it’s at your expense.

When you do stand-up, you put it all out on the line, every time, and dealing with hecklers isn’t the hardest part of the job. Dealing with the raw reality of it, baring your soul to a new crowd of strangers and making it funny, insightful, and compelling each and every time, keeping it fresh and new for them even when you’ve done it a thousand times before – that’s the hardest part. I have nothing but love for good stand-up, and nothing but respect for great stand-up comics. Each one has to create their own unique style to stand apart from a sea of others, a special and compelling character that is both individual enough to be recognizable and familiar enough to be relatable.

For my money, these are the best stand-up concerts of all time, and are must-see items for anyone who likes to laugh.

Best Classic Stand Up: Bill Cosby – Himself

The heart of stand-up is not telling jokes, it’s telling stories. Funny stories, poignant stories, stories that pull you in or let it all hang out. The greatest storyteller of them all is Bill Cosby, and this is the concert where he is at the top of his game. He manages to combine words, gestures, running gags, and most of all just the character of Bill into a tour de force performance that doesn’t require anything except him to keep you enthralled. The most magical moment for me is a single story that (if I recall correctly) takes over ten minutes to get from point A to point B, and by the time he gets to the end he’s already covered more comedic ground than many comics can do in an hour… and then comes the punch line that actually references back to something he said a half hour before. Pure comic gold.

Best Underrated Stand-Up: Christopher Titus – The Fifth Annual End of the World Tour

“If it was a good show that got canceled way too young, it must have been on Fox!” That should be the slogan for the network that canned Titus (along with everything they’ve ever touched by Joss Whedon, but that’s a different rant.) Fortunately I discovered this stand-up special by Christopher Titus many years later and was able to see that his particular brand of dark, cynical, and yet still somehow hopeful comedy is still alive and well. Covering a wide range of material in a frank, honest, and mature fashion that is distinctly unfashionable among most comics, Christopher Titus walks a very fine line that manages to be both wildly entertaining and deeply thought-provoking, as well as more than a little moving on occasion.

Best Angry Stand-Up: Dennis Leary – No Cure for Cancer

I love Dennis Leary in pretty much everything I see him in, but for my money this is and always will be his defining moment. His humor is at best irreverent and at worst vulgar, but it is always challenging: challenging the status quo, challenging what is acceptable, even challenging just how far you can push the boundaries of bad taste. He is a thinking man’s angry comic, critiquing modern society even as he criticizes  it.

And to all the Sam Kinison fans out there, let me be the first to say, and I’m pretty sure Sam would agree with me when I say this, fuck Sam Kinison. He was a no-talent hack, the shock-jock of stand-up who got by on a little humor, a lot of screaming, and a willingness to say absolutely anything. That’s not comedy, that’s Tourette’s syndrome.

Best Dirty Stand-Up: Eddie Murphy – Raw

In 1987, Eddie Murphy had nothing left to prove. He was at the top of his game. That was the year Beverly Hills Cop II was released, for crying out loud. So what on earth possessed him to do a stand-up film in a skintight purple leather suit? Pure genius, that’s what. This is Murphy at his best, and he lives up to the title of the film all the way through, in every sense of the word. His language, his subject matter (you’ll be saying “I want half!” for hours afterward), even his gestures are all direct, honest, and completely uncensored. It’s not for every audience, but I highly recommend it for everyone who can get behind it.

Best All Around Stand-Up: Eddie Izzard – Dress to Kill

I named this my best all-around for two reasons: first, because at the end of the day I just can’t pin down how else to define Eddie Izzard; second, I have almost as much fun watching other people try to describe his show as I do watching it, which is (for me) the mark of great comedy. He covers so much ground, and with such style and panache, if I were to try to say “this special is about this” I would miss about 90% of what it’s about, and that would miss the point anyway. What it’s really about is watching Eddie Izzard be Eddie Izzard: funny, frenetic, charming and delightful.

Honorable Mention for Lifetime Achievement:

Chris Rock

Honestly, I can’t pick out any one stand-up special by Chris Rock and say, “you must see this.” Just pick one, any of them will do. They’re all good, and for me he’s the best of a lot of great comedians who all seem to do the same brand of comedy. He just does it with that little extra bit of je ne sais quoi. I might even go so far as to say that Chris Rock is the new Richard Pryor.

George Carlin

No, I’m not focused on George because of his seven dirty words. To be honest I don’t think it’s all that great of a bit, although I do love him for doing it. I more love Carlin because he had such a great character about him, and while I didn’t agree with his politics, I think every aspiring comedian should be required to study him to understand timing and delivery.