Simon was engaged at the time of his death, having been previously twice married, including to the actress Jennifer Tilly.
Following a profile of Simon on 60 Minutes in 2007, CBS writer Daniel Schorn wrote in an online article that Simon was "perhaps the Renaissance man of the baffling, uncertain age we live in." Simon was diagnosed with terminal colorectal cancer in 2012 and given only three to six months to live. He bequeathed his $100 million estate to various charities which he actively supported during his lifetime.
"In the beginning, I was skeptical it could be successful, but I was not skeptical it could be good.
I was hoping for 13 episodes that my friends would like. If you do something trying to make your friends laugh and that you can be proud of, you can also be successful." Simon co-developed the animated series The Simpsons, which premiered on the Fox network in 1989 and has remained on air ever since.
Simon commented: "When I was there I thought I was underpaid. There was a very strange, very good sense of humor on that stage ...