According to the AFI Catalog’s write-up on “Some Like It Hot,” Wilder played ball with UA, and sought the involvement of Frank Sinatra. This obviously meant Curtis would play Jerry because Sinatra’s reputation as the ultimate ladies’ man had to be serviced. But while Wilder was friendly with Sinatra, he worried about his reliability. Per Ed Zikov’s biography “On Sunset Boulevard: The Life and Times of Billy Wilder,” the director once said, “I’m afraid he would run after the first take. ‘Bye bye kid, that’s it. I’m going. I’ve got to see a chick!’ That would drive me crazy.”
It was a very brief courtship, but it got far enough down the road that Wilder briefly considered Anthony Perkins for the role of Jerry.
Working in Wilder’s favor was his working relationship with Marilyn Monroe. He’d directed her in 1955’s sublime “The Seven Year Itch,” and she was keen to collaborate with him again. This was bad news for Mitzi Gaynor, who was up for the part of crooner/ukelele player Sugar Kane. UA knew of Monroe’s interest during Wilder’s pursuit of Sinatra, and, though this would’ve blasted the budget skyward (Monroe was seeking 10 percent of the gross, which meant Sinatra would’ve probably wanted 15 or a ton of money upfront), the studio was more than happy to foot the bill. Stars didn’t come any bigger in 1959 than Sinatra and Monroe.