"I remember sitting down with Keira while we were shooting and saying, 'What are you doing next?'" Curtis said of the actress, who played Juliet in Love Actually. "And she said, 'I don't think it's going to work. It's a pirate film and they always fail.'"
Curtis laughed at the recollection given that the first Pirates movie, which came out in 2003 and starred Knightley as Elizabeth Swann, grossed more than $650 million dollars and spawned multiple sequels.
A stand out moment for Grant, who played the prime minister, David, was his much-loved dance scene from the flick, with the actor revealing that he doesn't share the same fondness for it that fans do.
"I think I saw it in the script and I thought, 'I'll hate doing that.' No Englishman can dance when they're sober at 8 in the morning," Grant said. "... To this day there's many people and I agree with them, who think it's the most excruciating scene ever committed to celluloid. But then some people like it."
In addition to his unforgettable dance, Grant's David stole fans' hearts when he fell for a staffer, Natalie (Martine McCutcheon), a fact he mistakenly revealed by kissing her onstage at a children's pageant.
"The shock when they open the curtains for the first time and they saw us kissing. Their reactions were just amazing," McCutcheon said of the audience, many of whom were non-actors that were truly surprised by what they witnessed. "And it just felt magical."
Then there's Linney, who starred in the film as Sarah, a woman who often puts her own life on hold to take care of her brother, who's mentally ill. She does have a romantic scene, though, with her co-worker, Karl (Rodrigo Santoro).
"Rodrigo and I were both broken hearted when we made this movie," Linney revealed, before recalling that she once told her co-star, "Guess what we get to do all day long? We get to make each other feel better."
"I think you can see that in the scene," Linney said. "We're comforting each other in a way. It was very sweet."
Thompson starred in the flick as Karen, a woman who learns that her husband (played by the late Alan Rickman) has bought expensive jewelry for another woman and drowns her sorrows by listening to the Joni Mitchell album he gifted her.
"I handed it over to two of my favorite women in history -- to Joni Mitchell and Emma Thompson -- and let them do their work," Curtis said of the scene that features Thompson silently crying while her husband and children sit downstairs. "It is one of the few times in my life I've been in the company of genius."
Another fan-favorite storyline is that of Liam Neeson's Daniel, a widower who becomes a confidant to his stepson, Sam (Thomas Brodie-Sangster), as the tween deals with his first love.
"When I heard about this [special], I didn't even realize it had been 20 years. I couldn't believe it," Brodie-Sangster said. "I watched it for the first time this past Christmas since the premiere. I'd forgotten how good it was."
Brodie-Sangster also had kind words for his on-screen stepfather.
"Liam was amazing. He treats me like his son. He was absolutely lovely to me," he said. "Just created this environment where I was very comfortable. But at the time I thought I was pretty much a grownup... I was pretty serious about it. Looking back, I've forgotten how small and new I was."