Comedy For Hire with Jeff Ross

By Staff

The Meanest Man in Comedy, Jeff Ross, applies for a position at

Crowned the Roastmaster General, comedian Jeff Ross has set his sights on North America in his latest tour, “Jeff Ross Roasts America."  Known for lambasting the likes of Charlie Sheen, Pamela Anderson and Hugh Hefner on Comedy Central Roasts, we decided to see if the Meanest Man in Comedy has what it takes to work at

What position are you applying for?

Missionary. If that isn’t available I’d like to be Playboy’s official "Roastmasterbater General”.

What is your education and training related to this job?

Over one million insults delivered on time, on target, and under budget.

How comfortable are you around half naked women?

Very, very comfortable. If you can make a woman laugh at herself you can make her do anything.

You’re known as the Meanest Man in Comedy, how will that skill transfer to your job here?

I only roast the ones I love.  Just ask Hef.  I roasted him  once and he was a great sport.  At the time he was sleeping with seven beautiful  blondes. From the podium I said, “Hef,  I guess you have one girlfriend to put it in and the other six to move you around?”.  He laughed harder than anybody and we raised over half a million for charity.

What would your previous co-workers say about you?

That I’m a lot of fun - especially if there is a trampoline or a bouncy house around. And also that I’m really a nice guy underneath all the hair and blubber.

Have you ever been fired or quit a job?

No, but I was voted off Dancing With The Stars after the first commercial break. When I broke into my Cha Cha Cha people thought it was a telethon and tried to donate money.

Describe your worst day at work.

I’m lucky. I love my job. Never a bad day. Unless you count my recent show in Milwaukee when a cougar in a fur coat and heels kicked me in the balls because I asked her if she was a finalist on Bulgaria’s Next Top Model.

Where do you see yourself in 10 years?

Hopefully being interviewed in your magazine instead of your web site.

How do you react to instruction and criticism?

With an open mind and a clenched fist.

Describe the last major change you made. Why did you do it?

I fired my barber for making me look like a cross between Moammar Gadhafi and Harpo Marx.

Why should we hire you?

I’m much cheaper than Bill Maher and slightly better looking than Carrot Top.

What are your weaknesses?

Redheads, hot pastrami, and anyone who can’t take a joke.

When can you start?

Not until my current “Jeff Ross Roasts America” Tour winds down.  In every city I speed-roast volunteers from the crowd, so if you’ve always wanted to be roasted by a professional… this is your big chance. My tour schedule, as well as a naked picture of me are up at  Keep in mind that my live stand-up show is very sexually oriented - so if you bring a date you’ll probably get some action afterwards.

Do you have any questions for the company?

Do I get free access to That would really help me out during these long, lonely nights out on tour all by myself. xoxo

For Canadian tour date info:

For US tour dates:


Playboy Social