It’s been a while, but ITWorld.com is once again running an IT Underworld cartoon caption contest! Here’s how it works:

1. Go here

2. Look at the cartoon

3. Think up a funny caption

4. Enter your brilliant piece of comedy as a comment

5. Wait for us to pick your entry as the winner

6. Spend the $25 Amazon gift card on whatever you like! Feel free to buy me something with it…

Here’s the toon, but remember, you must enter your comment on the ITworld site in order to be considered.

Good luck!

Tags: caption contest, cartoon, IT Underworld, ITWorld, police, smart phone, sobriety test

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My latest IT Underworld cartoon for ITWorld.com. I draw a new one every week! That’s just how I roll.

Tags: cartoon, divorce, iPad, IT Underworld, ITWorld, love, spring, Windows 7

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My latest IT Underworld cartoon.

Tags: cartoon, doctor, health care, IT Underworld, ITWorld, laptop, nerd, nurse, pre-existing condition

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My latest IT Underworld cartoon.

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My latest IT Underworld cartoon.

Tags: cartoon, IT Underworld, ITWorld, Microsoft, smartphone, Windows, Windows Phone 7

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My latest IT Underworld cartoon.

Tags: Abraham Lincoln, cartoon, George Washington, IT Underworld, ITWorld, Presidents' Day

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My latest IT Underworld cartoon.

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My latest IT Underworld cartoon.

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My latest IT Underworld cartoon.

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My New Year’s Eve IT Underworld cartoon.

Happy (belated) New Year!

Tags: 2010, cartoon, Cast Away, IT Underworld, New Year's Eve, Tom Hanks, Y2K

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What better way to celebrate Thanksgiving – the best holiday of the year (well, aside from Super Bowl Sunday) – than with a cartoon?

To that end, imagine what the Butterball Turkey Talk-Line would be like if it were manned by the Microsoft support staff? Maybe something like this:

That’s my latest IT Underworld cartoon, a weekly tune that I do for ITWorld.com. If you like it be sure to tell your friends, family and neighbors. Heck, feel free to also Digg it. I won’t object.

Any love you can show it is greatly appreciated.

Have a great Thanksgiving! I hope you’ll be doing what I’ll be doing – eating and drinking myself silly. Remember, if you don’t, then the terrorists win.

Tags: Butterball, cartoon, Digg, IT Underworld, ITWorld, Microsoft, Super Bowl, Thanksgiving, turkey

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PC World – in their kind and infinite wisdom – has seen fit to pick my technology cartoon, IT Underworld, as one of the funniest tech cartoons on the web!

They even led off the article with this one that I recently did:

I am humbled and honored and would like to thank my family, the academy and one JR Raphael for a very fine piece of journalism.

Thanks, JR!

In other cartooning news, I’m posting my new editorial cartoons over on Open Salon, and a couple have already been deemed an Editor’s Pick! If you like them, please swing by and give them some love.

Tags: cartoon, IT Underworld, ITWorld

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As you may know, I draw a weekly comic called IT Underworld about the wacky, wet and wild world of IT for the web site ITworld.

We recently decided to start holding caption contests, where you can try your hand at writing the punchline to one of my cartoons. The winner receives a $25 Amazon gift card. Can’t beat that!

We first tried this last month and it was so popular we’ve decided to do it again! Here’s the latest caption contest cartoon:

To enter, go to the IT World site and add your caption as a comment. If you add your caption here, no matter how funny it is, it won’t be entered in the contest. Sorry, them’s the rules.

Good luck, biatches!

Tags: Amazon, IT Underworld, ITWorld

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As I write this 2008 is swirling faster and faster around the toilet bowl, about to be flushed away forever. It’s been a strange year for me, lots of ups (Sarah Palin!) and downs (the Penguins blew it in the Stanley Cup finals). However, December turned out to be very strong, comedy-wise! Behold, my highlights, such as they were, for this month.

David Letterman told a whole bunch of my jokes in December, starting with these two on the December 8 Late Show:

OJ Simpson was convicted on Friday to 33 years in prison, but it could be less with good behavior.

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On December 10 Dave told this one:

The Yankees have signed free agent pitcher C.C. Sabathia.

The deal is pending a physical by Madonna.

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Dave told this one on December 15:

Yesterday in Iraq a guy threw his shoe at President Bush.

Luckily President Bush was able to dodge the shoe. I believe he hasn’t dodged something like that since the Vietnam War.

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On December 17 Dave again told two of my jokes:

On this day in 1903 the Wright Brothers made their first flight.

Those first flights were rough, it was drafty, it was cold, it was cramped, there was no food – today we call that JetBlue.

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Finally, the last joke of mine that Dave told in 2008 came on December 18:

It’s Christmas time so it’s tip time.

I’m all set for that; earlier today I went to the bank and got a roll of quarters.

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To top it all off, I got my annual Christmas present from Dave – another Late Show jacket! Check it out:

So, all in all, it was a good ending to my monologue joke writing year! Thanks Dave!

On the cartooning front, IT World has decided to continue publishing my cartoon IT Underworld into the new year! I’ll continue to put out a new one of those every week – tell your friends!

Here is this week’s cartoon:

Finally, the year was capped off with the just about the best Christmas present I’ve ever gotten – fleece football pants! Tell me these aren’t sweet:

OK, bring on 2009!

Happy New Year!

Tags: C.C. Sabathia, David Letterman, football, George Bush, Iraq, IT Underworld, ITWorld, JetBlue, Late Show, OJ Simpson, Sarah Palin, shoes, Wright Brothers, Yankees

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I hope everybody had as nice a Thanksgiving as I did. I loaded up on gravy, mashed potatoes and pie – all of which has once again gone right to my hips. The holidays always wreak havoc on my figure.

Aside from the orgy of food, it was also a good week for comedy! I cranked out two more poorly drawn cartoons and David Letterman told two of my jokes on TV!

Let’s start with the jokes. First, Dave told this one on Monday’s Late Show (11/24/08):

Political insiders are now saying that Barack Obama and Hillary Clinton have formed a good working relationship but they don’t have a close personal relationship.

That’s right, Obama and Hillary have a good working relationship but not a close personal relationship – no, wait, I’m sorry, that’s Bill and Hillary.

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Then, he told this little throw-away line that I wrote on his Thanksgiving Day show (11/27/08):

I have a lot to be thankful for this year.

Sarah Palin, Eliot Spitzer, John McCain, Amy Winehouse, Andy Dick…

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Following on this Thanksgiving theme, IT World published my latest IT Underworld cartoon:

Last and pretty much least, I closed out the Thanksgiving week by posting yet another Schwilm cartoon:

OK, enough with Thanksgiving! Time to get to work on Christmas and Hanukkah material…

Tags: Amy Winehouse, Andy Dick, Barack Obama, Bill Clinton, Christmas, David Letterman, Eliot Spitzer, Hillary Clinton, IT Underworld, IT World, John McCain, Late Show, Sarah Palin, schwilm, Thanksgiving

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Am I the only one who thinks the presidential election season was too short? I was thoroughly enjoying it! In particular, I enjoyed that wacky Sarah Palin. Oh yes, you couldn’t make her up. She is a gold mine of joke material!

To wit, David Letterman told the following joke that I wrote on the Late Show the day after the election (11/5/08).

Now that the election is finally over, Sarah Palin is headed back to Alaska.

I know one thing: I wouldn’t want to be a moose now.

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You can also watch the video of the entire monologue here.

Now that the election is finally over I am drowning my sorrows in cartooning! it is not a pretty sight. See for yourselves:

My latest Schwilm cartoon:

My latest IT Underworld cartoon:

If you like ‘em, please spread the word!

In the meantime, the 2012 presidential campaign should be kicking off any minute here. Yay! I can’t wait!

Tags: David Letterman, IT Underworld, Late Show, moose, presidential election, Sarah Palin, schwilm

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Most of you probably don’t realize it, but Tuesday is Election Day! I know, I know – it really snuck up on me too!

My schedule for Election Day: up early to vote, go to work, come home and plant butt firmly on couch in front of TV, with laptop on lap to live Twitter as the results roll in! Be sure to watch for my tweets! Wait, that almost sounds dirty…

In seemingly unrelated matters, my third career as a semi-professional cartoonist continues on apace. Earlier today, the latest toon in my IT-centric comic, IT Underworld, was posted on ITWorld.com. Behold:

Be sure to go to the site, add a comment, give it a thumbs up, tell your geek friends to check it out, etc. etc.

Finally, on Halloween night, after taking the kiddos around to get free candy from the neighbors (heh, suckers), I posted a brand new Schwilm cartoon!

OK, I’m all out of plugs. Don’t forget to vote – unless you live in Florida, in which case it probably doesn’t matter much anyways.

Tags: election, IT Underworld, ITWorld, schwilm, Twitter

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Are you an IT professional? Do you spend your time toiling away thanklessly on servers, networks, desktops and answering dumb questions from annoying end users all day long?

Or, on the other hand, are you one of those end users that has to deal with scary and strange IT professionals, who can never seem to answer your questions in plain English and, more often than not, could use a bath or at least a breath mint?

Well, either way, do I ever have something for you!

My newest comedy endeavor is a comic for the web site ITWorld.com, called IT Underworld. The inaugural cartoon has been posted here:

The concept: IT Underworld is the story of George and Elias, two lowly foot soldiers in the IT army of a large company, and their daily battles with clueless end users and meddling executives.

New cartoons will be posted here.

The plan is to produce one cartoon per week, through the end of December. If the reaction is good, we’ll keep it going!

So, please, tell your friends. Pass the word. Visit the site, add a comment, give it a thumbs up. Hell, feel free to tattoo IT Underworld on your forehead.

You get the idea.

That is all.

Tags: cartoon, IT Underworld, ITWorld, tattoo

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