#TBT When Jon Stewart Starred on The Nanny

jon stewart the nanny
Photo: Everett Collection

After sixteen years, it’s hard to imagine Jon Stewart as anything else but the host of The Daily Show. But, sometimes you’ve got to go back to actually move forward. In this case, we’re going way back to 1997, when a fresh-faced Stewart, two years out from being named the host of The Daily Show, took a small romantic role as Bob “the short Jew” MD on the Fran Drescher–led sitcom, The Nanny.

On the nasally show, Fran falls hard and fast for Stewart’s character who can, by virtue of being a doctor, park anywhere—“even at the fire hydrant in front of Loehmann's." It’s later revealed (spoiler alert!) that there’s a reason for the spark: Fran and Bob are cousins. "That was one of my favorite episodes," Drescher told Vogue.com by phone. "I really love working with really talented comics because I think that they lend themselves to being really fine actors, too."

As a tonic before tonight's final Daily Show, we took a stroll down memory lane with Drescher to reminisce about that time she smooched Jon Stewart—way before he was everyone’s favorite fake news host.

jon stewart

Photo: Sony Pictures Television

Did you know Jon Stewart prior to him appearing on The Nanny?
I knew him as a stand-up comic. So I knew him enough to know that he was really up and coming. In the circles of comedy, he was definitely somebody who was stealing attention and getting noticed without question.

What do you remember most about working with him?
He’s really, obviously, smart, but also self-deprecating, and extremely charming. He would make fun of himself—how hairy he was, even his knuckles are hairy, that he’s of Russian Jewish descent, and that he was living on the Upper West Side of Manhattan—he was really very amiable.

Did you hit it off immediately?
He and I had an instant chemistry. I always tried to make all the guests feel really at home. It’s very hard to be a guest on a series; everybody’s so tight with each other. And because we needed to have an onscreen chemistry very quickly, I always kind of went out of my way to be very real and put people at ease.

Do you two still keep in touch?
Maybe a little bit in the beginning, but once he really took off with his show and got so busy, and then I became a cancer survivor and started running in a whole new direction. I think we kind of just lost touch—but not fondness. And after we would see other, it’s always a warm welcome.

What is it like to revisit your show after all these years?
I just saw it recently actually and I thought it was really good, really clever. A lot of the episodes I really, really still like and enjoy watching. We packed a lot of punch into 22 minutes. It was one of those magical experiences where it all comes together right and you capture lightning in a bottle. And it hardly ever happens in art or on TV with such a collective art form—but it did for The Nanny. And everybody felt it and everybody did the show!

Was The Nanny completely scripted or was there room for improv?
For the most part it’s scripted because we would rehearse all week before actually putting it on tape. Through the rehearsal process, there was a lot of opportunity to make suggestions and changes. We had to be very physical and comfortable with each other. I remember when Jon took me to his apartment on the show, and I was trying to act cool, but I was completely overwhelmed by the fact that this guy was so perfect for me. In the rehearsal process, we were just trying to work the material to make it as funny as possible. And because he was already entering the situation with my high respect and regard for him as a comedian, I was absolutely open to anything he had to say. I think that he was a little nervous because that might have been his first acting job.

He hid it well! You both seem like a well-matched pair.
Me and Jon are sort of cut from the cloth in real life. So the two characters that we were playing were comfortable and natural. I think Peter [Marc Jacobson] and I might have already been separated and Jon was married, so there was no love match there off-screen. But I remember thinking he was very cute, very nice, very talented—and if he wasn’t married, I might have made a play for him.