Written by Tom Wofford
Practically the first time Birmingham native (and Pelham High School alum) Julie Montgomery ever laid eyes on David Letterman on late-night television, she decided she was going to work for him. “My dad and my brother got me into Letterman early on, I became a huge fan, and even though I was only a teenager, I made up my mind I was going to work for him,” Montgomery says only a few weeks after attending Letterman’s retirement party, following 33 years as the most beloved, if not always the highest-rated, late-night talk show personality in America. “Dad was great about taking us to New York when we were kids and exposing us to everything the city had to offer,” Montgomery says. “It was actually on the NBC studio tour, talking to the NBC page who was leading it, that I started making my plans to work there.” Montgomery would eventually spend eight years working for the Letterman show.
Montgomery went after her goal with focus and determination and made her late-night dream come true with startling speed. Before she had even finished her mass communications degree at Auburn University (“My entire family are huge Auburn people; Auburn is in my blood,” she says), Montgomery spent four months as an intern on The Late Show With David Letterman. “I planned my classes and graduation around getting that internship with Letterman,” Montgomery explains. “The internship was supposed to be three months, but I wouldn’t leave,” she says with a laugh. “I stayed though the holidays.”
Hardly a decade after she set her sights on her ambitious goal, Montgomery took charge of one of the most coveted roles in TV: booking talent for David Letterman. After graduation, she took a job at a public relations firm in New York, but managed to get a temporary job back at The Late Show soon after. After that position played out, Montgomery reluctantly took a job in Atlanta, always keeping an eye on getting back to New York. Soon she was back at the show as an assistant to the executive producer, and after a move to the staff of Worldwide Pants, Letterman’s production company, Montgomery was hired into the talent department at The Late Show. “As a talent assistant, I did all the pre-interviews with the upcoming guests,” she says, “found out what the guests wanted to talk about, looked for stories Dave could discuss with them. It was great fun.” It wasn’t long before Montgomery was promoted and put in charge of booking the show’s talent.
Being a talent booker for Letterman was a job that kept Montgomery on her toes. “Everyone on the show stayed on top of things in our respective departments,” she says, “and the right talent was always a huge part of the show’s success.” So Montgomery not only made sure the show had the right mix of big names, but also she kept her ear to the ground constantly in search of up-and-coming celebrities and emerging television stars. “I was always looking for fascinating people who I thought had a great story to tell,” she explains. Montgomery was, in fact, the first person to put Ashton Kutcher on a late-night program. “That ’70s Show was brand-new, and Kutcher had not broken out yet as a big name when I booked him,” Montgomery says.
Perhaps one her biggest successes was the first-ever booking of Amy Sedaris on The Late Show, who then became one of Letterman’s favorites and went on to appear on the show a total of 30 times. “Amy had really only done Strangers With Candy and was not particularly well-known nationally, but she moved to the top of the list of the people Dave wanted back on a regular basis.” Sedaris, who was best known at the time as the sister of best-selling humorist David Sedaris, became a favorite of everyone on the show. “Amy is fantastic,” Montgomery says. “When she was on the show, there would be a huge shift in energy backstage, because she has such an infectious personality. She’d come in in her big flouncy dresses, and she always brought homemade baked goods for the crew. Everyone adored her.”
Once Montgomery hit her stride at The Late Show, her job was every bit as exciting as she imagined it would be when she was a teenager. She would wine and dine potential guests, greet them when they arrived at the studio and make sure they were settled in, then watch the late-afternoon tapings from backstage.
More often than ferreting out breaking artists for the show, Montgomery was handling the appearances of established personalities, including many of the biggest names in the business. “Jerry Seinfeld, Steve Martin, Will Ferrell, you name it,” Montgomery says, “I was working with one of my favorite entertainers almost every week.” While Montgomery says that almost all of the big names were usually easy to work with, with surprisingly rare diva behavior, she has particular praise for Ferrell: “Will Ferrell was so great, so nice, as smart and funny as you can imagine.”
Of course, not every guest went over perfectly, as Letterman had a well-earned reputation for allowing his less-than-stellar guests to simmer in their own flop-sweat. “Some of the brand-new twenty-somethings, they might try too hard to be clever, and Dave would get bored with them, and it showed,” she explains. Like many of the Letterman staff, Montgomery would find herself on camera frequently. “I probably did about 20 on-screen bits,” she says, “sometimes with some very famous people. It was a fast-paced, hectic job, but it might be as much fun as you can have at work.
“The years I worked on the show, Dave was quite hands-on, extremely involved in the show, writing a lot of the jokes himself,” she continues. “We were winning Emmys every year at the time, and it was an amazing time to be there.” It was also a thrill for Montgomery to get to see some of her favorite bands. “I didn’t book the musical talent, but those were great days when we had one of my favorites on, and I could watch them perform from only a few feet away. Pearl Jam and Foo Fighters, those were two of my favorites I got to see up close.”
In 2005, Montgomery moved on to MTV, then to Garden and Gun magazine, before starting her own public relations firm in Charleston, South Carolina. In May, Montgomery revisited her Letterman days as one of the 300 guests at his retirement party. “Dave is the best there ever was,” she says.
Montgomery’s work takes her all over the country and to Mexico, but she often has her hometown on her mind. “I don’t get back to Birmingham as much as I would like, but I’m very proud of what’s gone on there since I left,” she says. “When I was first in New York, I would say I was from Birmingham and I didn’t get much of a reaction. Now I don’t even get ‘Birmingham’ completely out of my mouth before people say, ‘What a cool town!’”