For Sale: Memories From One of Hollywood’s Most Enduring Love Stories

Shackles from the film “Cool Hand Luke”; a script from the 1963 comedy “A New Kind of Love”; the wedding dress that Joanne Woodward wore the day she married Paul Newman in 1958.

These artifacts, along with some 300 others, tell the story of a union between two of Hollywood’s most enduring film stars that lasted more than a half century. It began in 1953 and lasted until Mr. Newman, a magnetic titan of the screen, died in 2008 at the age of 83. Ms. Woodward, 93, a formidable talent, has kept a private life since she was diagnosed with Alzheimer’s disease in 2007.

The objects will also take on another kind of value later this year, when they are put up for sale in a series of auctions by Sotheby’s. If previous demand for Mr. Newman’s belongings is any measure, the events are likely to be lucrative: A Rolex he owned sold in 2017 for a record $17.8 million. Three years later, another of Mr. Newman’s watches sold for more than $5.4 million.

The auctions, which will take place both online and in person in New York, follow the recent release of “The Last Movie Stars,” a six-part HBO Max documentary series directed by Ethan Hawke and based on audio transcripts of interviews with the couple’s friends, colleagues and family members.

Mr. Newman’s posthumous memoir, “The Extraordinary Life of an Ordinary Man,” was also published last year.

“The family really felt that this was the right time to continue telling the story of their parents,” Mari-Claudia Jiménez, the chairman of Sotheby’s, said by phone on Wednesday. The proceeds from the sales, she added, would go to the family.

The items, most of them from the couple’s home in Connecticut, include family photographs and autographed scripts, as well as awards, props and costumes from films including “The Color of Money,” “The Three Faces of Eve” and “Butch Cassidy and the Sundance Kid,” Sotheby’s said.

Ms. Woodward’s wedding ring; autographed letters and photographs from Presidents Jimmy Carter, George H.W. Bush and Bill Clinton; antique furniture and art collected by the couple, as well as racing memorabilia kept by Mr. Newman, a keen racecar driver, will also go on the block.

Sotheby’s has estimated that an embroidered suit worn by Mr. Newman at a 1971 Ontario Motor Speedway race could sell for up to $25,000; that the “Cool Hand Luke” shackles could sell for up to $5,000; and that Ms. Woodward’s wedding dress could fetch up to $1,200. But Ms. Jiménez, the chairman, acknowledged that these estimates were very conservative.

“You put in very reasonable prices that get people excited about the possibility of owning this piece of history, or this piece of Hollywood memorabilia, and then you have so many people competing that, inevitably, it sells for many, many increments above what we had estimated it at,” she said. “You’ll see things that are estimated at $500 to $800 that end up selling for $20,000.”

Sales of celebrity memorabilia have historically turned a handsome profit. Steve McQueen’s hero car from the legendary chase scene in the film “Bullitt”? $3.74 million. The “Casablanca” piano? $3.4 million. Marilyn Monroe’s Golden Globe? $250,000.

But in the case of Mr. Newman and Ms. Woodward, both Academy Award winners, it is not just the relics of their lives on set that are up for sale.

The pair, most well known as Hollywood stalwarts, were also political liberals and philanthropists, who, according to a statement from their family, “dedicated their lives to pursuing the things that inspired them, whether personally, professionally, or as collectors.”

Their family said that they hoped the public would enjoy the collection, which offers a glimpse into who the actors were “beyond their glamorous Hollywood personas.”

In Mr. Newman’s memoir, he provided a glimpse of that inner world, describing the self doubt that had plagued him from a young age. “I’m always anxious about admitting to failure,” he said in the book. “To not being good enough, to not being right.” He also struggled with alcoholism.

When Mr. Newman met Ms. Woodward, he was already married, and the pair continued an affair for five years — a time that recent accounts of their lives have acknowledged was challenging.

Mr. Newman, however, said that meeting Ms. Woodward had awakened him.

In an interview in 2002, Ms. Woodward described the summer day when she met Mr. Newman, who, she said, had appeared at her agent’s office in a pristine seersucker suit “like an ad for an ice cream soda.”

At the very core of their relationship, Ms. Woodward added, was the capacity to make each other laugh. She added, “and he sure does keep me laughing.”