Jeffrey Ross Roasts Ryan Dempster

After the game yesterday, we headed down to the Vic Theatre to see Jeffrey Ross.  If you have never seen Jeffrey Ross perform (and you don’t have delicate sensibilities), he is pretty damn funny.  He generally can be found doing the celebrity roasts that Comedy Central has brought back from the Dean Martin days.


It turns out Ryan Dempster was in the crowd and he was enticed on stage to get a little heat from the Roast Master General.  

First he started by nibbling the corner by taking a shot at Chicago sports teams in general:

Cubs, Bears, Bulls… it sounds like the different sections of a gay dating site.

Then he started pounding the strike zone:

Look at you.  Who knew Ralph Malph could pitch?  You look like Opie with a pitching arm.

Ryan Dempster has 107 wins.  He also has 107 losses.  That’s like saying, “I have 10 million dollars in cash and I owe AMEX 10 million dollars.”

You’ve walked more people than people have walked dogs.

I haven’t seen anyone choke more since David Carradine.

Come on Ryan, take it like a man. Don’t get all tough. Jesus, the Bears have a better chance of winning a World Series before the Cubs.

Dempster was a good sport and he got a shout out for the Ryan and Jenny Dempster Foundation in the process.  Before heading back to his seat he tried his own brand of comedy which shockingly did not involve a Harry Caray impression:

A lot of people don’t know that Jeff is a big environmentalist, so after the show make sure you recycle all your plastic cups, like Jeff recycles his jokes.

Boom! Roasted.


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I used to write lots of things about the Cubs. Now I sometimes write things about the Cubs.