Paul Reubens shall always be remembered as Pee-wee Herman—a cheerful character who made everyone laugh. He was best known for his work as Pee-wee Herman. This role not only earned him Emmy nominations but also an iconic and irreplaceable position in pop culture.
However, in real life, Paul chose a life of normalcy and kept most of it private.
Paul, raised in upstate New York, chose to stay grounded even when he was famous. Here’s a closer look at the man behind Pee-wee’s iconic red bow tie. If you always wondered what his real life was like, let’s dive deeper.
Humble beginnings in Upstate New York
Paul Reubens, born Paul Rubenfeld, was originally from Peekskill, New York. He spent his early years in Oneonta, a small town away from the glitter and glam of Hollywood.
Did you know that as a young boy who had dreams of making it big, he once wrote a letter to Walt Disney, hoping to kickstart his acting journey? This is a story that the man himself recalled during an appearance on Live With Kelly and Michael.
As his family eventually moved to Sarasota, Florida, this is where Paul spent most of his teenage years. His parents, Judy and Milton Rubenfeld, ran a lamp store in town. Judy worked as a teacher, and Milton, a former pilot who flew for the British Royal Air Force and the U.S. Army Air Forces during WWII, later became a car salesman. While staying away from the world of television and film, his upbringing gave him strong roots.
Love, Relationships, and Personal Life
Paul Reubens was a deeply private person. While he never married, in 1989, he held what he called a “mock wedding” with Chandi Heffner at Doris Duke’s estate, Shangri La. This symbolic ceremony included a temporary license signed by Imelda Marcos and a performance by actor Jim Nabors.
From 1993 to 1999, he dated actress Debi Mazar. Reubens, who was fond of Mazar, always spoke highly of their relationship, saying that her positivity helped him through a particularly dark time in his life. “It was a gift,” he once said, describing how being with Mazar helped bring him back to life emotionally.
Reubens didn’t have children and chose to keep his romantic life out of the spotlight after that. Even with his playful on-screen personality, he valued privacy and sincere relationships in his real life.
Leaving a Lasting Legacy
Paul Reubens passed away on July 30, 2023, at the age of 70 after a private battle with cancer. Before his passing, he asked fans to support cancer and dementia research in memory of his parents.
Following his death, his team released a statement celebrating his legacy.
“Paul bravely and privately fought cancer for years with his trademark tenacity and wit,” they wrote. “He will forever live in the comedy pantheon and in our hearts.”
In memory of his late parents, Reubens requested that fans donate to Stand Up To Cancer or organizations that support Alzheimer’s and dementia care and research. His legacy isn’t just about laughter — it’s also about heart, courage, and generosity.
“Pee-wee as Himself” airs in two parts on HBO on May 23 and will be available to stream on Max.
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Paul Reubens’ Family: Everything You Need to Know