Member of the week: Jeff Caldwell, Comedian

Jul 3, 2007

Our member of the week is Jeff Caldwell. Jeff is professional comedian, telling jokes for the last 20 years in comedy clubs, for corporate clients, and even on television. Jeff has appeared on Comedy Central, and on both "The Late Late Show with Craig Ferguson" and "The Late Show with David Letterman" on CBS. Jeff is currently touring. To see if he will be coming to a city near you, check out Jeff’s tour schedule on his website. To find out more about the life of a stand-up comedian, check out Jeff’s profile on our Yellow Pages, and our interview with Jeff below.


1. What has been your most interesting project?

Doing a set on the “Late Show with David Lettermanâ€? last September. It was a long-held goal and met my every expectation (video available on at A big part of the fun was meeting Elvis Costello in the green room.

2. Why did you decide to go freelance?

Freelancing is the nature of the beast for standup comedy; I’ve had a development deal with CBS for my own sitcom (didn’t get on the air, sadly), which was like having a salary for a year, but otherwise it’s been gig-to-gig.

3. What tip would you give to a new freelancer or someone who is considering going freelance?

Have a pot of cash before you begin—there will be lean times and unexpected expenses, and a little liquidity will help prevent selling off valued possessions at pennies on the dollar.

4. What is your favorite spot in the city in which you live?

Elysian Park here in Hoboken—an amazing view of the Manhattan skyline, the one that Brando and Eva Marie Saint overlook in a great scene in “On the Waterfront.â€? Gorgeous at night.

5. What is your inspiration?

I’m inspired by great comedians and comedy writers. Re-reading any Bruce Robinson, or “Lucky Jim,â€? or watching Al Franken or Bill Maher gives me hope that it can all be worth it.