The 51-year-old music mogul made £35 million last year from his various business interests including his SyCo music label and reality TV shows including `The X Factor` and `America`s Got Talent`, leading to his inclusion at number six on the annual Sunday Times Rich List of Britain`s music millionaires, which is due to be published by the newspaper this weekend.
Simon - who owns homes in Beverly Hills, Barbados, Malaga and Dubai - has bypassed music legends including Sir Elton John, Sir Mick Jagger and Keith Richards on the list, but his assets are dwarfed by others including former Zomba Records owner Clive Calder who took the top spot with a £1.3 billion fortune and rival Simon Fuller, whose £375 million wealth earned him fifth place on the list.
Other musicians who made the list were Beatles legend Sir Paul McCartney, with a £495 million fortune, and Sting with £180 million.
Even though Simon - who is engaged to make-up artist Mezhgan Hussainy - can claim to be one of Britain`s richest men he admitted he still enjoys playing the National Lottery, but would never tell anyone if he scooped a million pound jackpot.
He said: "I still buy lottery tickets. I still play. But I tick the box that says no publicity so no one would know."
However, despite his vast wealth, Simon has recently admitted he often gets in "dark moods for no reason" and has often considered going to see a psychiatrist to deal with "a number of issues" he has.
He explained: "If I ever decided to go to a psychiatrist, it would be a long session. I have always thought that I do have a number of issues that probably need dealing with, because I am quite odd in some ways.
"I get very dark moods for no reason. I just sit on my own for days."