“There’s a couple of pictures of Sinatra and Dean Martin – I think in the end I always like pictures of Dean Martin the best because he just seems so chummy. Sinatra’s so intense; Dean’s so relaxing. There’s a wonderful picture near the front of the book of the two of them backstage at a TV special, I believe it was Judy Garland: they were real friends and fans and any time she had one of her myriad comebacks they supported her however they could. They’re in their tuxedos and there’s just a cloud of cigarette smoke between them. It’s a beautiful photo. It’s the sort of thing Caravaggio would have painted. In a lot of these pictures, the cigarette smoke is amazing.”

“There were images from Peter Lawford’s beach house from 1960 with Frank Sinatra, Marilyn Monroe, Peter Lawford, Patricia Kennedy Lawford and May Britt, Sammy Davis Jr’s wife. They’re all sitting around in beachwear, someone’s got a Polaroid camera and they’re all playing with it. Lawford’s beach house is part of Rat Pack lore because that’s where the Kennedys and the Rat Pack partied. But to see Marilyn Monroe among them in a picture at that time is just shocking.”

“The one common mistake people make is that they think any time Frank, Dean and Sammy got together it was a “Rat Pack thing”. They were more like the Travelling Wilburys! The period that most interested me in Rat Pack Confidential was when they coalesced showbiz power and political and criminal power, during the Kennedy administration, before their ties to the Chicago mob were severed. That actually only lasted a couple of years. What’s shocking is people think, ‘Could that happen today?’ I always say, ‘Hell, no!’ If you were in a restaurant and you saw a huge rapper with some terrible mafia guy, you would Tweet about it. Back then everything was behind this veil of gentlemanly secrecy that the media abetted. These guys could carry on brazenly but never be exposed. It’s funny. If you told people in 1960 that Frank Sinatra was running around with John Kennedy, Marilyn Monroe and the head of the Chicago mafia, they would say, ‘Cool! I wish I was doing that.’ Today it would be a front-page scandal on every paper in the world. The time has changed. There really was a time when awful and brazen behaviour was celebrated and envied. We’re much more moralistic now, ironically.”

The Rat Pack by Shawn Levy (Real Art Press, £400) is available to order now. reelartpress.com

via:GQ-UK