Schimmel married his first wife, Vicki, in 1977, and they had four children together. Their son Derek died from cancer at the age of 11. Schimmel later divorced and remarried, having two sons with his second wife, Melissa.

Schimmel was born in the Bronx, New York City, the son of Betty and Otto Schimmel, Jewish survivors of the Holocaust. He was voted class clown during high school and was in the United States Air Force for one year during the Vietnam War era. In 1980 he was living in Scottsdale, Arizona, where he was working as a stereo salesman. His career began when, at the urging of his sister, he performed at a comedy club’s open-mic night. A club owner in Los Angeles offered to make him a regular, but when Schimmel moved there he found that the club had burned down.

In 1998, Schimmel suffered a heart attack. In June 2000, he was diagnosed with non-Hodgkin’s lymphoma. His treatments included chemotherapy and required long stays in the hospital. Schimmel detailed this experience, in a humorous light, in his book Cancer on Five Dollars a Day* (*chemo not included): How Humor Got Me Through the Toughest Journey of My Life.

In 2000 Schimmel had developed and completed a TV pilot for a show that would bear his name for the FOX network, with Brie Larson and Vicki Davis as his two daughters. The show was put on hiatus when Schimmel became ill from cancer and eventually cancelled. The opening scene is available on YouTube.

Schimmel had a complicated relationship with his first wife, Vicki. “We got married, then got the marriage annulled, then got remarried, got divorced then remarried,” and then their son Derek became ill from cancer and died. They eventually divorced permanently in 2000 when Schimmel became romantically involved with his second wife Melissa.

Schimmel was arrested in Calabasas, California on May 2, 2009 as a result of an alleged confrontation between himself and his wife Melissa. The district attorney eventually declined to press charges, citing insufficient evidence. On May 8, 2009, Melissa Schimmel filed for divorce, citing irreconcilable differences. Schimmel claimed, during an interview with Howard Stern, that his wife had cheated on him with their neighbor, although he admitted he had no solid proof. Schimmel also stated that he was bankrupt due to some of the actions that Melissa had taken with his money.

During an interview on The Howard Stern Show on January 28, 2010, Schimmel announced that he developed cirrhosis as a result of a hepatitis C infection from a blood transfusion that he received while in the Air Force. His cirrhosis had progressed to the point that he was working to be added to the waiting list for a donated liver.

On August 26, 2010 in Scottsdale, Arizona, Schimmel was a passenger in a car driven by his 19-year-old daughter Aliyah. After veering off the road to avoid hitting another vehicle, the car flipped onto its side and came to a stop in the shoulder of the Loop 101 freeway. Schimmel was hospitalized at John C. Lincoln hospital (North Phoenix) in serious condition, while Aliyah was hospitalized in stable condition. Schimmel’s son Jacob, who was also in the vehicle at the time of accident, was uninjured. On September 3, 2010, Schimmel died of his injuries.