In real-life, Joy had two sons: Douglas Gresham (who was depicted in this movie) and David Gresham (who was not). David was born in 1944, and Douglas in 1945. After their mother's death, David and Douglas continued to live with their stepfather, C. S. Lewis. In contrast to his mother, stepfather, and younger brother, David was less interested in converting to Christianity, and while still a child living with Lewis, he started to return to Judaism. According to Edwin Brown's book "In Pursuit of C. S. Lewis", Lewis was very supportive of David's interest in Judaism, including finding a kosher butcher to supply his meat.

Sir Anthony Hopkins prefers to memorize lines on his own, while Debra Winger prefers extensive on-set rehearsals. To accommodate Winger, Producer and Director Sir Richard Attenborough rehearsed with her, reading Hopkins' lines.

In one of the scenes, in which Douglas Gresham (Joseph Mazzello) is reading in bed, he is reading The Hobbit by J.R.R. Tolkien. Tolkien was a good friend, and colleague of C.S. Lewis.

Douglas Gresham (along with his brother, David) became the heir to C.S. Lewis' literary estates, and is one of the producers of The Chronicles of Narnia film franchise.

After Joy's death, C.S. Lewis kept notes on his grief, which he published as "A Grief Observed" under a pseudonym.

Many of the students and staff of Magdalen College, Oxford, England, objected to the restrictions imposed on their movement on the grounds during April and May 1993, especially as it coincided with end of year exams. To prevent a student-led halt in production, a Q & A evening was held in the college bar, with Producer and Director Sir Richard Attenborough, Sir Anthony Hopkins (C.S. Lewis), and Michael Denison (Harry Harrington).

The title is from The Chronicles of Narnia: The Last Battle, by C. S. Lewis, from the chapter "Farewell to Shadowlands".

The scenes of the traditional Mayday celebrations in Oxford, were filmed on the actual night and morning of April 30 to May 1, 1993. On Magdalen Tower were the actual choristers of the college chapel, but with restricted space, due to the minimal crew and camera. Medium shots had been taken of extras in boats on the river, and the intention had been to take long shots of the real-life crowd below. However, an unusual thick low mist made much footage unusable, so the extras were recalled a week later, with others to cover Magdalen Bridge.

This movie is, indirectly, descended from the television version, Shadowlands (1985), with Joss Ackland as C.S. Lewis, and Claire Bloom as Joy (Davidman) Gresham. Both were written by William Nicholson, but in-between, Nicholson adapted the television version into a stage play, and then later re-worked the stage play into this version. The two share some differences, for example, as in her real-life, Joy is depicted as having two sons in the original version, whereas she appears to have only one, Douglas, in this one. There are also no scenes of Lewis as a professor in the original, whereas his interaction with one of his students, Peter Whistler, is a fairly prominent subplot in this version.

Joseph Mazzello played the director Richard Attenborough's grandson in Jurassic Park (1993) and The Lost World: Jurassic Park (1997).

Joy Gresham's husband was William Lindsay Gresham, an author whose best known work was made into a movie with Tyrone Power, Nightmare Alley (1947).

The books that C.S. Lewis (Sir Anthony Hopkins), the preceding two initials stand for Clive Staples, he's known to his friends as Jack, is selling during his book signing are copies of The Silver Chair, part of his popular series The Chronicles of Narnia. Interestingly, this book is the most enigmatic in the series, as the title chair doesn't materialize until near the end of the story, and is featured in only one chapter, "In the Dark Castle".

Barbra Streisand was asked to direct and star, but declined so she could pursue The Normal Heart (which she never made).

Sir Nigel Hawthorne, who played the role on stage, was replaced in this movie version by Sir Anthony Hopkins, because Hawthorne was still almost unknown internationally.

The "Bird and Baby" was the nickname C.S. Lewis and his friends used for "The Eagle and Child" pub, where they met regularly.

This was Michael Denison's final film before his death on July 22, 1998 at the age of 82.

Gerald Sim (Superintendent Registrar) was the brother-in-law of the director Sir Richard Attenborough. After Oh! What a Lovely War (1969), Young Winston (1972), A Bridge Too Far (1977), Gandhi (1982), Cry Freedom (1987), and Chaplin (1992), this was his seventh and final appearance in one of Attenborough's films.

This was Gerald Sim's final film before his death on December 11, 2014 at the age of 89.

Sir Richard Attenborough replaced Sydney Pollack as director. When he came on-board, he had Sir Anthony Hopkins and Debra Winger in mind to play the lead roles.

Michael Denison (Harry Harrington) had been at Magdalen College during C.S. Lewis' time. He had met him, but had never been taught by him, and had graduated by the time of the events in the story.

Despite his great popularity in British movies during the decade after World War II, this was Michael Denison's only work for the cinema after 1960, and it proved to be his last movie.

This was Norman Bird's final film before his death on April 22, 2005 at the age of 80.

The original Broadway production of "Shadowlands" by William Nicholson opened at the Brooks Atkinson Theater on November 11, 1990, ran for one hundred sixty-nine performances, closed on April 7, 1991 and was nominated for the 1991 Tony Award for Best Play.

Theatrical movie debut of James Frain (Peter Whistler).

This was Robert Flemyng's final film before his death on May 22, 1995 at the age of 83.

Michael Denison replaced Peter Barkworth.

Graham Sinclair (uncredited) is the voice of the taxi driver in the country.

The cast includes two Oscar winners: Sir Anthony Hopkins and Julian Fellowes; and two Oscar nominees: Debra Winger and Peter Firth.