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George Harrison and Madonna worked together on one of the more unsuccessful projects of his career. Harrison started the production company HandMade films in 1978 to finance Monty Python’s Life of Brian. Over the years, the company had a number of successes, but it hit rough financial waters. One financially unsuccessful project was Shanghai Surprise, which starred Madonna and her then-husband, Sean Penn. According to those who knew Harrison, he never quite recovered from the disappointment.

George Harrison stands behind Madonna as they pose for photos.
George Harrison and Madonna | Georges De Keerle/Getty Images

The former Beatle started HandMade films because of a Monty Python project

Harrison became involved in the film industry when the initial backer pulled out of Life of Brian because of its controversial script. Harrison’s friend Eric Idle came to him for help because the former Beatle was a fan of Monty Python and extremely wealthy. 

“Well, I’m what they call the executive producer,” Harrison told Rolling Stone in 1979. “What happened was that I helped to raise the money for them in order to make the film when the previous backer pulled out. As I’m a Monty Python fan, I wanted to see the movie – I like to go and have a laugh too – and a friend suggested that I try and raise the money. So we just got a loan from a bank. It’s a risk I suppose.”

With his business associate Denis O’Brien, Harrison founded HandMade films. The company put out 23 films in 10 years. 

George Harrison was let down by the failure of a Madonna film 

By the late 1980s, HandMade had produced a number of unsuccessful films. One of their biggest flops was also their most expensive. In 1986, they released the critically and financially unsuccessful film Shanghai Surprise starring Madonna and Penn.

“Basically, the script was crap,” HandMade employee Brian Shingles said, per the book Very Naughty Boys by Robert Sellers. “The whole project was awful and you get beguiled by the names. When you look at it now, it’s just embarrassing. The acting is embarrassing. It’s more notorious for its publicity than anything it contained.” 

The film was HandMade’s most expensive movie to date. The film made just over $2 million of its $17 million budget.

“I have the feeling that George never quite recovered from that,” Michael Palin wrote in the forward to Very Naughty Boys. “He remained generous, but felt compromised and he began to draw back. Once that happened, the end was in sight. HandMade had many able people at the helm, but the spirit that drove the ship had to come from George.” 

Madonna was starstruck by George Harrison 

Soon after Penn and Madonna signed onto the film, producer John Kohn took them out to dinner.

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“One thing I’ll never forget after we’d signed Sean Penn and Madonna, I took them out to dinner to celebrate and suddenly into the restaurant comes George Harrison and sits in the booth with us,” Kohn said. “And Madonna was so astounded and open-mouthed. George was his usual charming self, welcoming them on the picture and saying how he was looking forward to working with them, and then he left. And I remember Madonna said, ‘There goes a legend.'”