Before Gwyneth Paltrow was cast as Viola de Lesseps in Shakespeare in Love (and won an Oscar for her portrayal), another A-lister was wooed to take on the role.
Julia Roberts Was The Original Choice

Julia Roberts was Hollywood’s star du jour when she showed interest in the project, which was then being developed by producer, Edward Zwick.
Her Complicated Involvement In The Movie

Zwick, who was also the director behind Legends of the Fall and Glory , recently penned an essay titled Not to Be for Air Mail detailing the making of the movie – and Roberts’ complicated involvement in it.
Universal Pictures Wanted Her
First, he revealed that Universal Pictures only agreed to fund the film if Roberts was in it.
They’d ‘Cough Up The Dough’ For Her

“The mere possibility of having the ‘Pretty Woman’ wearing a corseted gown got the studio excited enough to cough up the dough,” Zwick wrote.
Traveling To London For The Chemistry Reads

Weeks later, he traveled to London with the actress to have her do chemistry reads with the actors being considered for the role of William Shakespeare.
Roberts Wanted Daniel Day-Lewis As Shakespeare

Now, Roberts had her heart set on getting Daniel Day-Lewis cast opposite her, saying he was “brilliant,” “handsome,” “intense,” and “so funny!”
He Was Doing Another Movie

However, the actor told Zwick he had already committed to another film, In the Name of the Father .
‘Be My Romeo’

Roberts vowed she could “get him to do it” and proceeded to send two dozen roses to him along with a note saying, “Be my Romeo.”
She Didn’t Want Any Other Actor

She even had Zwick cancel a round of chemistry reads with other actors because she was so sure the My Left Foot star would say yes.
He Said No
It didn’t work.
Roberts then had to attend a chemistry read with Ralph Fiennes, and Zwick got candid about what happened that day.
‘Barely Acknowledged Him’

“Even as Ralph did his best to elicit the famous smile, Julia barely acknowledged him,” he wrote. “I’m not suggesting she was deliberately sabotaging, but it was a disaster nonetheless.”
‘He Isn’t Funny’

He continued, “I tried to catch Ralph’s eye to apologize as he left but he couldn’t get out of there fast enough. After he was gone, I turned to Julia, awaiting her reaction. ‘He isn’t funny’ is all she said.”
No One Was Good Enough
They went through two more weeks of casting, but no one was good enough for Roberts, it seemed.
Who Were The Other Actors?
Among the actors who were considered for the role, Zwick named Hugh Grant, Rupert Graves, Colin Firth, Sean Bean, and Jeremy Northam.
The Final Read

Next, the Mystic Pizza star agreed to read with Paul McGann. She entered the room “in full period costume” and began to say the lines. Then Zwick finally realized what was wrong.
‘The Problem…Was Julia’

“There was no magic,” he wrote. “The problem wasn’t the script. Or Paul McGann. It was Julia.”
She Left The Project
He explained that although he had tried to motivate her, she’d sensed his unease. By the following morning, she’d checked out of her hotel, flown back to the U.S., and left the project.
The Aftermath
At that point, Universal had already spent $6 million, sets had been built, and costumes were being created. The studio vowed to get Roberts back on board but failed.
The Movie Was Completed With A Different Cast

Shakespeare in Love was later completed by Miramax Pictures headed by Harvey Weinstein, with Gwyneth Paltrow as Viola and Joseph Fiennes – Ralph’s brother – as Shakespeare.