Best caption wins a date with this man… if you can tear him away from his family of balloons.

[Schadenfreude does not guarantee the quality of the date, nor, who's "dream" will be represented on said date. You enter at your own risk. However, The Jordan Years is a pretty kick ass band - so you would at least have that going for you. Be sure to check out our show with them on May 21 at The Gallery Cabaret! This contest is open to EVERYONE. Seriously, everyone. Roger will date anyone once.]

There are a two things you should know about me. First, I’m a greatest hits kind of guy. I would rather just wait until the compilation is released. I have little interest in exploring anyone’s B side. Second, I’m always impressed by celebrity – on any level. I enjoy seeing the John Kapelos’ of the world just as much as I do the Tom Cruises’. To that end I ran into this guy while visiting the Big Apple recently and I couldn’t have been more thrilled.

Can anyone tell me where you might have seen this man before? If you guess correctly I will give you “something to poop on”.

What was Air Force 2 doing flying around the Statue of Liberty? I’ve been traveling, and all I’ve got are headlines and pictures of people running in the streets because Air Force 2, along with a couple F-16s, were flying around Ground Zero and the Statue of Liberty.

It seems to me that no one still has answers as to the who, what, where and why. Whatever happened to investigative journalism? I understand print is dead, but with all the cable news channels, you would think ONE of them would ask those basic questions, and, not be satisfied with the “Ummm… I don’t know.” kinda answers.

I think it was a diversion. I’ve seen DAVE a few times – and each of those times, there’s a big public display to distract the public from what was really going on. And that’s what needed to happen here. The Prez wasn’t where he was supposed to be, so they ‘authorized’ the pilots to go on a little joyride so the real Prez could be where he needed to. It has something to do with the fact that the guy who shook Obama’s hand in Mexico died 24 hours later. Real Prez has a mutant strain of the Swine Flu – and so Fake Prez had to take his place.

You heard it here first. That’s not really Obama. It’s Fake Obama.

Got a better idea? Best one wins… this Coke Zero bottlecap to add to their “My Coke Rewards”*
*=does not include shipping

Last night, we wanted to check out the CIF page to find out which friends were coming to town. Sandy typed in www.chicagoimprovfestival.com and we realized that it wasn’t the site (it is .org). And we also realized that nobody owned it. Seriously, it was unregistered. Memo to CIF: not a smart move. So we bought it. And after today, it cleared and is our domain. So now the jokes have been flowing and the ideas brewing on what we should put on this site. Can you help? Vote or give us ideas in the comment section. This week is the festival week so it should get major accidental traffic. It’s the little things in life…

Who wants to go with me? I’m heading over to Sutton Place Hotel on Sunday. I’m planning on being Paris Hilton’s BFF. I mean LOOK at me (check me out in the Kanye video). Not only am I street, but I know what’s hot, I know Rhymefest, I get into fights with Opie and Anthony, I tried to save Michelle Leigh’s job – I am about as celebrity as you get in Chicago. Fuck Billy Dec, it’s all Stephe Schmidt. [Casting in Chicago this weekend]

You don’t know what it was like to keep Adam from posting his suggestions for this caption. For once, this was about you guys strutting your stuff, and letting the world know you’re funny too! Thanks to all who entered – let’s run through the paces:

Third Prize is you’re fired – and that goes to: Big Red Mole: Desperation setting in, Sen. Clinton shocks America when she replies to a question about family values with her very animated version of The Aristocrats. Obama doesn’t get it.

Second Prize, a set of steak knives, goes to: phil r: “Yo! Beachball!! Pass it up!!!”

And First Prize – a Cadillac t-shirt – goes to…. johanna: So what if you need 2 hands to hold your testicles, B-man. I have to push my balls out of the way to see.

Hey johanna – stop by a Rent Party, announce yourself, and we’ll have your t-shirt waiting for you! Thanks for playing, we’ll get another one of these up Monday!

We’re still taking entries.  Remember, it doesn’t have to be politically relevant – it just has to be funny!  We got some real strong suggestions – but that doesn’t mean YOU can’t suggest something!  Deadline is Friday, noon!  Caption this photo.

Ok – for realz this time. A REAL contest with a REAL prize. We’re gonna start this one slow and easy to welcome the new commenting ability on the site… All you have to do is caption this photo:

Drop it in the comments, easy enough, right? What do you win? A t-shirt!

Comment away, and we’ll pick the winner by Friday this week!