Today I chat with Jim Windolf, a Vanity Fair contributing editor who previously was a writer for The New York Observer.Can you tell us how you got to your spot at Vanity Fair today? Where did you get your journalistic start?
I got a Master's in English at University of Texas at Austin in 1990, then taught English at Friends Seminary high school in New York for a year. After that I sent out my college newspaper clips to 25 or 30 newspapers and magazines. I got all no's, except for one--The New York Observer, a weekly paper in Manhattan, asked me to interview. Graydon Carter, now editor of Vanity Fair, had just taken over The Observer following his departure from Spy magazine. I loved Spy and knew it cold, which helped me not make an idiot of myself in the interview. I was hired as an intern. I did research, fact checking, coffee fetching, wrote a few articles, and even got to drive the van. I stayed at The Observer nine years--as media columnist, features writer, and then executive editor. Graydon Carter, who had moved on to Vanity Fair, had been keeping an eye on my Observer work, and I got a job as one of the magazine's articles editors in 2000. I stayed in that job three years, before becoming a contributing editor for the magazine. I now write five or six long feature stories a year.

Which stories have been the most fun for you to work on?
Probably the article I wrote about three men from Mississippi who had made their own home-movie version of Raiders of the Lost Ark when they were teenagers ("Raiders of the Lost Backyard," March 2004). I loved reporting it because the story involved 20 years in the lives of three people. It was a fun challenge to try to pack it all into one story, and the magazine gave it a lot of room.

How would a freelancer work their way to the point where they'd be writing the huge features (especially the luxury or celebrity-themed ones) for Vanity Fair? Or are those always in-house?
The best way for a new writer to break into the magazine is by having an exclusive line into a great story that no one else knows about. The story should be dramatic, full of interesting characters and conflict. A murder is always nice.

In your career, have you learned anything in particular on how to get great quotes from interview subjects?
Anybody can get good quotes. It's all about putting in the time. You have to immerse yourself in the lives of the people you're writing about and keep the tape recorder running. I like to do a mix of long face to face interviews (sometimes in a quiet room, sometimes while doing other things) and phone calls. New writers may not realize how much material you have to amass to get enough good stuff for a long magazine story. For one article that ended up not running, I had 300 pages of transcribed interview notes. For the Raiders story it was about 180.

When do you make time to write, and is it difficult to work in so many different styles?
Hard to answer. I like writing outside of journalism but have made only a few thousand dollars from short stories and humor pieces over the last ten years. I'll just say I get the same excited, almost manic feeling when I'm writing a good reported story as I do when writing a piece of fiction or humor that seems to be working. It's all storytelling--all part of the same thing to me.