Fran Drescher Confesses: I Had a Secret Crush on a Young Jon Stewart on ‘The Nanny’!

Fran Drescher Reveals She Had a Crush on a “Super Cute” Guest Star on ‘The Nanny’

Fran Drescher’s iconic role as Fran Fine on The Nanny made her a household name and cemented the show as one of the defining sitcoms of the ’90s. Running for seven seasons, the series blended humor, heart, and fashion, creating a “fish out of water” story that fans still love in syndication today. Drescher often shares stories from her time on set, and in a 2017 interview, she revealed that one particular guest star left quite an impression on her — and not just professionally.

What ‘The Nanny’ Was All About

Premiering in 1993 on CBS, The Nanny starred Drescher as Fran Fine, a vivacious, outspoken Jewish woman from Queens, New York. Fran unexpectedly becomes the nanny for a wealthy Manhattan family, quickly winning over the widowed patriarch, Maxwell Sheffield, and his three children. The series drew heavily from Drescher’s own life experiences, giving the show a unique authenticity. Audiences were captivated by Fran’s charm, comedic timing, and heartfelt interactions, making the series a critical and cultural hit.

A Guest Star Who Made Drescher Take Notice

Although The Nanny wrapped in 1999, Drescher continues to fondly recall her favorite moments and guest appearances. One story that stands out is her experience working with a young Jon Stewart on the 1997 episode titled “Kissing Cousins.”

Drescher admitted that she found Stewart “super cute” and had an immediate rapport with him. Despite her attraction, she didn’t make a move — largely because Stewart was already in a relationship at the time.

“You know, I would have gone for him in a New York minute, but I don’t go after anybody’s man — ‘cause you have to narrow the pool somehow,” Drescher joked in the interview.

Jon Stewart’s Early Career Before The Daily Show

Before becoming the legendary host of The Daily Show, Jon Stewart built his career in stand-up comedy and acting. Born in 1962, Stewart began performing stand-up in New York City in 1987 and quickly became a familiar face in the comedy scene. He also wrote and performed sketches for television programs, including Caroline’s Comedy Hour.

By the early ’90s, Stewart had hosted The Jon Stewart Show on MTV, while also taking on guest appearances in other TV shows, including The Nanny. His stint on the sitcom, though brief, left an impression on Drescher, showcasing his comedic timing and charm long before he became a household name.

A Peaceful Personal Life

Since 2000, Stewart has been married to Tracey Stewart, maintaining a relatively private personal life. At the time of his The Nanny guest appearance, the couple was already together, which is why Drescher kept her crush strictly professional.

Even decades later, Drescher fondly recalls the experience, proving that sometimes the sparks behind the scenes are just as interesting as the ones on camera.

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