John Cleese – $8.25 Million, Montecito

In the summer of 2008, actor John Cleese reportedly lost a whopping $7 million on selling his home in Montecito, California. The Equestrian-style ranch home had initially been listed by the “Pink Panther 2” actor for $18.78 million but managed to close the deal a few months later at only $11.06 million.

Located just down the road from Oprah Winfrey’s former residence, the 14.6-acre residence was back on the market in 2016, this time at a price tag of $8.25 million. In November 2021, Cleese protested the cancel culture in Hollywood by pulling out of a speaking event at Cambridge University.