You might say that Haleigh Raff is a go-getter.
In her career as a talent booker for shows like “Late Night With Conan O’Brien,” “The Martha Stewart Show” and currently for Piers Morgan on CNN, it’s the 39-year-old Raff’s job to go out and bag A-listers for on-air appearances — plus find future stars, amusing zoologists, fashion experts, you name it.
Growing up outside Cleveland, Raff had her sights set past Ohio early on. Her high school yearbook quote was: “One day I’m going to work for Barbara Walters.”
Ambitious and extroverted, the Syracuse University graduate climbed the ladder from office assistant at NBC to segment producer on “Regis” and “The View.”
Now married with two kids and living in Midtown, the behind-the-scenes vet runs her own booking firm, Raff Media. She sat down with @work to tell us what it’s like coaxing Hollywood stars to get in front of the cameras — without a script!
When did you first become interested in working in entertainment?
I always interested in entertainment. Growing up in a typical Cleveland suburb, I used to look out the window at night and pretend it was Manhattan, with tall buildings, lights. I knew I’d wind up in New York one day.
How did you break in to the business?
After college, I came to the city in ’94 and called everybody I knew, called in any favors. Still, it took me a year to get an interview. I did odd jobs to pay the bills. Babysitting. I answered phones and ran for coffee at an ad agency.
Finally, I heard that Michael Weinberg, a producer at “Late Night With Conan O’Brien” was hiring a segment producer’s assistant, so I called him literally like 50 times. Finally I got an interview, but he said there were 50 other people up for the position. I left and got downstairs at 30 Rock, and thought, I don’t have this job. So I went back up to his office and said, “I have to have this job. I will do your laundry. Whatever it takes.” So, I got it. Although he never made me do his dry-cleaning.
What were your duties?
A segment producer does pre-interviews with the celebrities coming on the show, so the assistant sets it up with the publicist, checks newspapers and magazines and compiles a folder on each guest. This was pre-Internet, too.
You eventually worked at “Conan” as a segment producer. How does that pre-interview process go?
You talk to the talent and craft these great stories. An interview segment is seven minutes on the air. We want anecdotes with a beginning, middle and end.
In terms of guests, there’s only a handful that every show wants. People like Alec Baldwin, Rosie O’Donnell, Adam Sandler, Tom Hanks. People who deliver the goods every time. Sometimes it’s because they’re game to do anything. Like, we had Martha Stewart on the show and she drank a 40-ounce beer with Conan. Other people, like Will Ferrell, will show up with bits in mind. Like, he’ll show up with a tear-away suit and nothing but purple short-shorts underneath.
Those guests make your job easy?
All the “SNL” guys were amazing. They were such a team. When Sandler would come on, Chris Farley would come down to 6A and hang around the green room cracking everyone up. Conan would come by, and they’d just start riffing. At that point, I wasn’t even working.
What do you do if someone cancels at the last minute?
Call Al Roker [laughs]. No, that’s a scramble. You look through your recent publicist pitches and hope people are in town. At NBC, we had some great people in the building. Like Brian Williams, the network anchor. Even at the last minute, he could prepare something. He always delivered the goods.
Between stints at “Conan,” you bounced around, working with Regis Philbin among others. What was that like?
Producers would hold their own cue cards. My very first day, the first segment I produced, he’s reading my card, “Please welcome our first guest, Tori Spelling!” and I dropped the cue cards everywhere. So, of course, he calls me out on the air. “Look at our new producer.” The camera pans to me. I’m beet red. But I was able to pull it together. I was there for a very enjoyable year and a half.
Then you worked at “The View,” fulfilling your yearbook pledge.
I did. I did fashion, beauty, celebrity, medical segments, a little of everything. The challenge was briefing five women with your ideas a half-hour before show time.
You returned to “Conan,” but turned to booking talent. Why the shift?
A position was opening up, and it was a new challenge. As a talent booker, you’re selling the idea of a celebrity making an appearance. You’re on the phone all day, meeting publicists and creating relationships. As a former producer, I could try and land tough guests by giving an idea of how the segments might go.
What’s the trick to landing hesitant stars?
As a booker, you have to be aware of every way to get talent. Maybe they’re getting behind a charity or a cause, directing or producing something. Get creative and find an incentive. We had Charlize Theron on Piers talking about her charity. Demi Moore and Ashton Kutcher came on talking about the campaign against human trafficking.
What’s something people don’t know about your job?
Probably that my favorite part is finding new talent. For example, years ago Jonah Hill’s publicist pitched me at “Conan.” This was before anyone knew him. But Jonah sat in my office for a half-hour at 30 Rock and made prank phone calls. I didn’t stop laughing. So I book him, and he killed in his segment. Now he’s on “Conan” all the time.
That’s the thing. When you book an unknown, they’re loyal to your show after they hit it big. That’s a great feeling as a booker.
How is it different booking for Piers Morgan?
I’m booking someone for a half-hour discussion or even a whole hour. We want someone with something to say, people like Oprah, Howard Stern, George Clooney. Bill Maher was everything you’d want in a guest. Russell Brand is very smart and funny. Or someone like Sarah Silverman. She can do seven minutes on a talk show, but on “Piers” we learned who she is, what motivates her, her thoughts on comedy.
What’s the longest it’s taken to coax a guest to appear?
Michelle Obama. A year and a half of talking to the White House director of communications and coming up with ideas. Shot down 10 times, and finally all the stars aligned.
What’s your advice for someone wanting to break into your end of the entertainment business?
Once you’ve been around a while, it starts to get easier finding jobs. It’s almost a fraternity. You’ve worked with people who’ve moved on, and they remember you. You build a good reputation. But that first job is the hardest one to get. You can’t lose your confidence. Be persistent, but don’t be annoying. And that line is hard to define.