Bob Wiltfong might not be a catchy household name, but this news reporter-turned nationally known comedian is everywhere lately. He was billed as “The World’s Greatest Spokesperson in the World” in a series of recent Nationwide Insurance ads, and he’s also been a correspondent on The Daily Show with Jon Stewart. This Saturday, Wiltfong returns to his old stomping grounds to do a benefit show in Benson, with the proceeds going towards renovating the Benson Theatre.
Despite some big-city buzz his career has garnered, Wiltfong sounded like a regular guy, still deeply in touch with his Midwestern roots on a phone from his home in L.A., where he’d just returned from an audition that morning.
“I actually grew up near Immanuel Hospital, and I went to high school at Creighton Prep,” Wiltfong says when I ask about his history with the Omaha area. The youngest of six kids, his family tree actually goes way back, as his great-great-grandfather was the first governor of Nebraska.
Wiltfong went to college and graduated from the University of Kansas, and then sought out a career in traditional news journalism. “I thought I would get into corporate journalism because it satisfied my interest in history and current events,” Wiltfong explains, “It satisfied this need to perform that I’ve always had.”
It was a career that saw him hop-scotching around the country, landing TV news gigs in Louisiana, Kansas, and ultimately, the weekend anchor spot on News 12 Long Island in New York. It was a well-paying, steady job that even saw Wiltfong scoring four regional Emmy’s for his work as a news reporter. But deep down, he wasn’t happy.
“About a year into my career in TV news journalism, I realized I did not like what I was doing,” Wiltfong remembers. It was the choppy, cyclical, headlines-only nature of journalism that was part of the problem.
“I felt like we were never doing full justice to the news.” 9/11 was the other part.
Wiltfong lost a close friend, a photographer named Glen Pettit, on that tragic September morning. It was a loss that caused him to reevaluate what he was doing in life, and Wiltfong realized what he really wanted to be doing was comedy. So he joined an improv team in New York City, the Upright Citizen’s Brigade, and started crafting his style.
The transition from news to comedy was a change. “It was a little bit awkward yet natural,” Wiltfong says. “There was a big pay cut at first, but life became immediately more fun.”
Wiltfong describes his style as alternative comedy.
“I don’t want to be pigeonholed as just doing one thing,” he explains, “I want to push the art form. It’s still definitely Midwest-inspired though, and it’s not your traditional, ‘let’s go write a sitcom’ type of humor. It’s good intentions-gone-awry type humor.”
That heartland charm might be part of what helped him stand out so brilliantly as a correspondent on The Daily Show. It was the gig Wiltfong calls the biggest moment of his career so far. “It was doing what comedy should be doing, and that’s making you laugh and think.”
He played a wacky go-to news guy on the satirical show, the first former real-life reporter to do so. Overall though, Wiltfong calls his experience on Stewart’s show a mixed bag.
“It was the perfect marriage of news and comedy,” Wiltfong explains. “But the main problem was that you are putting comedy writers in charge of supervising other human beings. It led to an odd, dysfunctional workplace.”
He laughs, “Some of the most miserable people I’ve ever met are comedians. I was just too optimistic for that culture.”
Since then, Wiltfong has scored guest roles on Chappelle’s Show, as well as a few movies such as The Hoax and Definitely, Maybe.
He’s bringing his new one-man improv routine “I Don’t Know Dick” to Omaha. The title isn’t meant to be a dirty joke or anything; it’s actually a true statement about a guy named Dick that Bob just didn’t know very well.
“It’s actually about a real-world inspiration for me, in that the first home my wife and I bought in New York was from an older gentleman named Dick. He had been married to his wife for around 50 years when we bought the home. He took a liking to my wife and I so much so that when he left us the house, he left behind a bottle of champagne and a note, along with all of the love letters that he and his sweetheart had sent each other,” Wiltfong explains.
“There are about 250 of these letters, I haven’t read these letters, but I kept them with the idea of one day I have to sit down and read these and write a book about this. So I’m actually using them as inspiration to do a one-person improv show. Each show, I’ll bring like a 100 of the letters, an audience member at random chooses one of those letters for all of us to read together as a group. And then based on the content of that letter, I use that as inspiration to improvise as a comedian for 25 minutes.”
Wiltfong seems intent on pushing himself, stretching his comedic muscle in unique ways.
“Yeah I’ve been doing improv comedy for 15 years,” he recalls, “If I’m not good at it by now, I should be.”
Wiltfong shared some straightforward advice for aspiring comedians.
“If it’s in your head or in your heart to do an endeavor, do it. Somebody out there is probably already making money doing that too.”
He’s looking forward coming back to Omaha for his upcoming show to support the historic Benson Theatre. “You know, Benson was in something of a decline when I lived there, but now it sounds like it’s having a rebirth. I’m really excited about these Benson Theatre renovations.”
Wiltfong’s show will take place at PS Collective, which is right next door to the theatre. His performance will be streamed online – allowing anyone in the world to drop in and donate to the cause. The Benson community has rallied together this year to try and raise the funds to bring the theatre back into a fully-functional workspace for local artists to get their start.
“The Project has raised $32,000 to date, which allowed us to lease the historic theater space and save it from being turned into a nightclub. We're now working to raise another $50,000 to purchase the building from The Lund Company,” emailed
Monty Eich, marketing director of the Benson Theatre group.
“I think it’s a great idea to have a place here locally to help cultivate our own talent,” Wiltfong adds. “Omaha has spawned some incredible artists; wouldn’t it be great if we had a stage for the next Alexander Payne, Bright Eyes, 311, and all sorts of other artists?”
Bob Wiltfong plays this Saturday, Sept 1, 8pm at PS Collective, 6056 Maple St. Tickets are $15/person and can be purchased at improvomaha.com. For more information, please visit bensontheatre.org.