Exclaim!
The Best Book-to-Film Adaptations
By Rachel Ho
Oct. 22, 2025
Transforming the intricacies of literature into a visual spectacle has yielded some of cinema’s greatest films. In recent years, Colleen Hoover has taken up the mantle left by Nicholas Sparks as the go-to romance author whose books are inspiring studios across Hollywood.
The latest Hoover book to receive the cinematic treatment is Regretting You, a romantic drama directed by Josh Boone about a family weathering their grief following a tragic accident. Allison Williams and Dave Franco star as Morgan Grant and Jonah Sullivan, in-laws whose spouses (played by Scott Eastwood and Willa Fitzgerald) die in a car crash. As both navigate life without their partners, and Morgan without her sister, details of the accident leave more questions than answers.
Mckenna Grace also stars in the film as Clara Grant, Morgan’s daughter. Clara’s already-complicated high school life becomes a whole other journey after losing her father and sensing there was more to the accident that claimed the lives of her dad and aunt.
Grab your popcorn and tissues, as Paramount Pictures’ Regretting You hits theatres across Canada on Friday, October 24. As we escape into the world of the Grants and Sullivans, here are five other book-to-film adaptations that ignited our imaginations.
Breakfast at Tiffany’s (1961)
A classic film whose iconography lives on through dorm room posters and Halloween costumes, the exploits of Holly Golightly find an audience with each new generation. Adapted from a novella written by Truman Capote in 1958, Breakfast at Tiffany’s follows the naïve socialite and her unlikely love story with her new neighbour Paul Varjak, a struggling writer.
A film known for Audrey Hepburn and George Peppard’s chemistry (despite the unfortunate casting of Mickey Rooney in yellowface), Blake Edwards’s gentle direction and Franz F. Planer’s rich cinematography captures the heart of Capote’s story. The film was nominated for five Academy Awards, including one for Hepburn, and won two for its music, including Best Song for Henry Mancini’s “Moon River.”
Clueless (1995)
Perhaps only William Shakespeare can rival Jane Austen for the number of film adaptations made of their work. The British film industry in particular has grabbed onto the heartache and beauty of Austen in a truly unique way; however, one American production emerged in the ’90s to bring Austen across the Atlantic in the most Hollywood way possible.
Amy Heckerling’s Clueless transforms Austen’s Emma Woodhouse from the mildly spoiled, highly intelligent 21-year-old living in Hartfield estates into Cher Horowitz, a supremely spoiled but good-natured high school student rocking up to her Beverly Hills classes in an Audi convertible. Clueless presents a coming-of-age story in outrageous extremes while still finding a genuine sentimentality that makes Alicia Silverstone’s performance one for the ages. The film continues to inspire fashionistas today and spawned some of the best lingo the ’90s had to offer. As if!
The Curious Case of Benjamin Button (2008)
F. Scott Fitzgerald’s short story The Curious Case of Benjamin Button features one of the most tragically human premises in literature. The reverse physical progression of the titular character, who never finds a connection with his peers and only experiences shame from his family, creates an existential mind-meld with readers.
David Fincher didn’t adapt Fitzgerald’s short one-to-one; he made several changes to the legendary text, but, most importantly, his Oscar-nominated film injected a love story set across time. Fincher spun the film slightly away from its satirical source material, turning it into a movie about connection. A tremendous film centred on stunning performances from Brad Pitt and Cate Blanchett, The Curious Case of Benjamin Button proved itself to be one of the best films of the decade.
The First Wives Club (1996)
When The First Wives Club premiered in 1996, critics were lukewarm in their response to Diane Keaton, Bette Midler and Goldie Hawn as scorned wives seeking justice for their unappreciated marital efforts. Based on the novel by Olivia Goldsmith, The First Wives Club became a box office hit in spite of critics’ attempts to warn them off the film, and it exists today as a cult classic.
Although broken marriages make up a large part of the film’s narrative (as well as the book’s), friendship forms its heart. The chemistry between Keaton, Midler and Hawn carries the movie from strength to strength, with just enough camp and silliness to break up the heaviness of their individual pain. It’s easy to see how The First Wives Club reinvigorated the careers of its three leading ladies — just watch their fantastic “You Don’t Own Me” finale.
Ordinary People (1980)
The directorial debut of Robert Redford, Ordinary People highlights the insurmountable challenge families face in the wake of an unexpected death. Based on Judith Guest’s 1976 novel, the film follows the Jarrett family as they rebuild their home after a sailing accident claims the life of the eldest son and sends their younger son to a psychiatric hospital due to a suicide attempt.
Donald Sutherland and Mary Tyler Moore star as Calvin and Beth Jarrett, the grieving parents who respond very differently to the situation. Redford’s direction and Alvin Sargent’s script intricately explore the delicate and fraught nature of family, while affirming the strength of familial bonds. A heartfelt film that won a multitude of awards and readily occupies “Best of the ’80s” lists, Ordinary People endures as a classic family drama that delivers compassion to our darkest moments.
The latest entry in the canon of book-to-film adaptations, Regretting You opens in theatres October 24. Tickets are available now.
