Movies That Make Boomers Cry

Sometimes you just want to escape into the magic of the silver screen and have a good cry, even if it’s courtesy of your own TV or laptop. There are countless films that are considered tearjerkers, each with its own dedicated following and a slew of iconic stars, like the recently departed James Caan, who took centerstage in more than just "The Godfather" and "Misery." Read on as we sample some of those cinematic gems that rarely fail to bring a tear to the eye of those “of a certain age.” 

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Why It Makes Boomers Cry: Laugh if you will, but this animated classic produced by Walt Disney isn’t for the faint of heart. Moviegoers follow Bambi’s growing up, from playing with his fellow forest friends to learning about the dangers of the world in a story about life, love, and loss. Oh, and in a most jarring – and scarring – scene, Bambi’s mother is killed. As The Wrap put it, “Very few movie scenes are more soul-crushing than the shocking demise of Bambi’s mother.” 

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Why It Makes Boomers Cry: Stories about unexpected romances and characters thrown together who form a friendship that turns into something more are, again, the stuff of daydreams. This British film follows the story of a bored suburban housewife (Celia Johnson) and an upstanding doctor (Trevor Howard) who must decide what continuing their relationship would mean to those around them, eventually coming to a heartbreaking decision. “One of the most vivid, impassioned and painfully believable love stories ever committed to celluloid,” Time Out called it.

Why It Makes Boomers Cry: An angel is sent from Heaven to help a desperate, suicidal bank owner (James Stewart) to show him that, despite his feelings of failure and defeat, the world is infinitely better with him in it. How? By showing him what the world would be like if he’d never existed at all. Though initially a box office flop, thanks to the movie becoming a public domain property in 1974 (Republic Pictures forgot to renew the copyright), it came to be a television staple for years — and a holiday weepy for generations. 

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Why It Makes Boomers Cry: This was a remake of a 1935 version starring Irene Dunne and Robert Taylor, but with Rock Hudson and Jane Wyman starring this remake was destined to be memorable. Its plot, though, made it much more. Hudson is a wealthy playboy whose reckless behavior plays into the death of a celebrated doctor. Though the incident was inadvertent, he is committed to helping the widow but, drum roll please, falls for her along the way. A Variety reviewnotes that, “It is a sensitive treatment of faith told in terms of moving, human drama which packs emotional impact.”

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Why It Makes Boomers Cry: Years before its reincarnation as “Sleepless in Seattle,” this version of the romantic tale pairs Cary Grant and Deborah Kerr as star-crossed lovers who, though each engaged to others, fall in love on a cruise ship and agree to meet up in six months later on top of the Empire State Building. The events of that fateful evening are the stuff of legendary romances.

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Why It Makes Boomers Cry: This classic Disney film starred Tommy Kirk as a teenager helping his family run a Texas homestead while the father is away — and the stray dog that comes to be an integral part of their lives — is the prototypical tearjerker. Let’s just say rabies and a rifle play into its most heartbreaking moment. 

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Why It Makes Boomers Cry: It takes quite a production to make a decidedly familiar story seem fresh and still maintain its emotional impact. This cinematic version of the popular Shakespearean tragedy is buoyed by the chemistry between Olivia Hussey and Leonard Whiting in the title roles, at the time they were indeed teenagers themselves and lend an authenticity to the movie. As Roger Ebert wrote decades after the original release, this production truly hit a nerve: “The movie opened in the tumultuous year of 1968, a time of political upheaval around the world, and somehow the story of the star-crossed lovers caught the mood of rebellious young people who had wearied of their elders’ wars.”

Why It Makes Boomers Cry: Everyone fell in love with Jennifer Cavalleri (and the actress who played her, Ali MacGraw), the working-class Italian girl who made it to Radcliffe on her brains (and musical talent. Cavalleri fell in love with Oliver Barrett IV, aka “Preppy” (expertly played by Ryan O’Neal), the smart and oh-so-entitled Harvard law student. Despite protests from their families, the lovers in this playfully antagonistic campus romance get married — and then comes a shockingly unexpected diagnosis of a terminal illness. Cue the waterworks.

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Why It Makes Boomers Cry: Even tough guys cry … that goes for moviegoers and characters in this film that debuted as a made-for-TV movie on the true story of Brian Piccolo, a Chicago Bears football player who would die of cancer, and his friendship with teammate Gale Sayers. Its intensity would help propel the careers of both James Caan (Piccolo) and Billy Dee Williams (Sayers). “On its own, somewhat obvious level, ‘Brian's Song’ worked,” said The New York Times. “Not least in its favor were two exceptionally fine performances: James Caan as Brian Piccolo and Billy Dee Williams as Gale Sayers.”

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Why It Makes Boomers Cry: Can’t you just picture Robert Redford’s Hubbell in that sharp Navy uniform – and already hear the movie’s iconic theme song? This period film, set in the 1930s to the ’50s, follows the story of seemingly mismatched lovers Redford and Barbra Streisand. The pair’s ill-fated union is threatened (and eventually broken) by their differing core beliefs. It’s a bittersweet tale to say the least.

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Why It Makes Boomers Cry: It seems like every generation will be getting its own cinematic version of “A Star is Born.” Boomers may have delighted in the Bradley Cooper-Lady Gaga 2018 version, but it’s this version — featuring Babs (aka Barbra Streisand) as the rising star and Kris Kristofferson as the has-been rocker — that’s likely seared in memory. While this version was not universally lauded, there are some fans who will defend it to the end.

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Why It Makes Boomers Cry: This remake of the 1931 classic brought fresh energy — and even more tears — to the drama of a once-great boxer (Jon Voight) and his son (a very young Ricky Schroder). The return of the boxer’s former wife (Faye Dunaway) sets him on a path to try and regain his past success so he can hold onto his son. If the final scene — a heartbreaking tour-de-force by Schroder (“Wake him up!”) as Voight dies in front of him — doesn’t make you cry, then your heart is made of stone. As The Week reported, “‘Scientifically’ speaking, the film boasts the saddest movie scene of all time, according to researchers who concluded that ‘The Champ’s heart-walloping punch has never been equalled.”

Why It Makes Boomers Cry: Robert Redford directed a stellar cast — Timothy Hutton, Mary Tyler Moore, Donald Sutherland and Judd Hirsch — in this sharp-edged family drama that explores the aftereffects of the accidental death of the family’s elder son.

Why It Makes Boomers Cry: Families have issues. That’s true in life as in film. This star-studded movie teamed up veteran actor Henry Fonda with his real-life daughter, Jane Fonda. With Katharine Hepburn playing the matriarch, this New England-based drama traced the story of the adult daughter’s attempt to repair her strained relationship with her father.

Why It Makes Boomers Cry: This film, which takes place in 1940s Brooklyn, features flashbacks to tell the tale of Sophie (Meryl Streep) and her harrowing Holocaust journey in which she was forced to make a choice that would break anyone’s spirit. The heartbreak, though, is far from left in the past, as her “new life” with Nathan (Kevin Kline) will also end in a most tragic way. As Entertainment Weekly has said, “She’s a damaged, haunted heroine who’s not likely to live happily ever after. But the real poignance lies in Sophie’s tremulously maintained illusion of hope. Hers is a brave but fragile front that conceals the depth of her guilt and sorrow as a Holocaust survivor. You don’t cry for Sophie because she dies so young, but because she has suffered so long.”

Why It Makes Boomers Cry: A mother and her daughter – Shirley MacLaine and Debra Winger – share a bond that carries them though life, from bad marriages to illness, and do it all with a trademark mix of laughter and tears. Keeping audiences both laughing and crying in turn, the film, noted critic Roger Ebert noted, was like real life: “The most remarkable achievement of ‘Terms of Endearment,’ which is filled with great achievements, is its ability to find the balance between the funny and the sad, between moments of deep truth and other moments of high ridiculousness.”

Why It Makes Boomers Cry: This historical drama is a sweeping tale that follows the life of an African-American woman (Whoopi Goldberg) living in the South who was married off to an abusive man and dreams of being reunited with her sister in Africa. As Entertainment Weekly wrote, “Steven Spielberg’s searing adaptation of Alice Walker’s novel about a group of disparate black Southerners consistently makes our eyes fill to the brim as their stories unfold over three decades.”

Why It Makes Boomers Cry: This film delves into the Holocaust story in an unexpected way, taking moviegoers into a 1943 French boarding school where the story follows a trio of new students who are actually Jewish boys, brought there to evade capture by the Nazis. It’s a harrowing story seen through children’s eyes, giving it unexpected depth. The Times (UK) wrote, “Without being sentimental, the drama is incredibly moving as the muted light plays over young faces that are about to face the unknowable evils of the adult world.”

Why It Makes Boomers Cry: Another film focusing on female friendship, “Beaches” celebrates the lifelong bond of two women who met as children vacationing at the Jersey Shore. Played by Barbara Hershey and Bette Midler as the adults, the women’s relationship — the highs and the very lows — are traced to the bittersweet end.

Why It Makes Boomers Cry: Carpe diem! Robin Williams is truly memorable as the new English teacher at an all-boys prep school, a no-nonsense institution that takes great pride in its traditions and lofty standards. Williams’ character’s unorthodox methods truly connect with his students, portrayed by actors including Ethan Hawke and Robert Sean Leonard. Their young lives are filled with immense pressure, but Williams leads them to look at life in a new way. Still, a shocking death and its aftermath are haunting.

Why It Makes Boomers Cry: This groundbreaking film follows the lives of a small group of friends, gay and straight, as they experience the devastating effects of the AIDS epidemic in its earliest years. With an ensemble cast including Bruce Davison, Campbell Scott, Dermot Mulroney, and Mary-Louise Parker, it would introduce moviegoers to a reality many had only read about.

Why It Makes Boomers Cry: This tear- and laughter-inducing tale of a group of women in a small Louisiana town — all connected through a hair salon — is a look at female friendship across generations. They savor their good fortune and face tragedy, equal parts Southern sass and sadness. The exploration of the relationship between Julia Roberts’ character, a diabetic who becomes pregnant and the shocking way that storyline plays out, and her mother, played by Sally Field, is unforgettable. As a Time Out critic wrote, “It makes a shameless bid for your heart, aiming to have you smiling one moment, sniffling the next.”

Why It Makes Boomers Cry: An unbroken bond between lovers, one that remains even after death, is at the heart of this romance/fantasy/thriller that starred Patrick Swayze, Demi Moore and a memorable pottery wheel. She’s an artist, he’s a banker who will be murdered — and he tries to protect her, even from the grave.

Why It Makes Boomers Cry: This film tackled the AIDS crisis head-on  in a hauntingly realistic way. Tom Hanks played a closeted lawyer whose HIV status is exposed, leading to him losing his job at a Philadelphia firm. The subsequent fight is about him suing for discrimination with the help of a somewhat sketchy — and initially homophobic — attorney played by Denzel Washington. While it certainly can be viewed as a courtroom drama, the film, as critic Roger Ebert wrote, delved deeper, offering a heartbreaking glimpse into what was new territory for many moviegoers: “Even as the case is progressing, the film’s center of gravity switches from the trial to the progress of Beckett’s disease, and we briefly meet his lover (Antonio Banderas) and his family, most especially his mother (Joanne Woodward), whose role is small but supplies two of the most powerful moments in the film.”

Why It Makes Boomers Cry: This is a love story of a different kind — an epic Holocaust story that spotlights how businessman Oskar Schindler (Liam Neeson) transformed into a humanitarian, protecting his more than 1,000 Jewish workers from the concentration camps and probable death. It’s incredibly sad, but how sad is it? A poll by Entertainment Weekly proclaimed it the saddest movie of all time.

Why It Makes Boomers Cry: It’s easy to get swept up in this tale of a family living in early 1900s Montana, a father (Anthony Hopkins) and his dashing sons, played by Brad Pitt, Aidan Quinn, and Henry Thomas. Theirs is a rough-hewn life, with experiences ranging from devastating deaths to intense sibling rivalries to tearful reunions. It adds up to quite the emotional trek into the Old West. In a decidedly mixed review, critic Roger Ebert noted that the film served as “a throwback to the days when Hollywood didn’t apologize for passionate stories involving three brothers whose fates are intertwined with that of a legendary woman, as they're all outlined against the Big Sky.”

Why It Makes Boomers Cry: Meryl Streep and Clint Eastwood brought the spark to this utterly romantic tale, one that had many a moviegoer daydreaming of such a romance. Eastwood plays a photographer who comes to a small Midwestern town in 1965, encountering a local wife whose family is away at the state fair. They grow close and experience an intense (if brief) love affair. It’s a testament to taking chances and following your heart, but in the end, Streep decides to forego her own happiness to put her family first. Entertainment Weekly called out a “Kleenex moment” from the film: “As she makes a trip into town with her husband a few days after rejecting Eastwood, she spots him standing in the rain, mournfully staring at her. You stop being able to tell the difference between the torrential downpour on screen and your own tears.”

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Why It Makes Boomers Cry: It’s a scenario many are familiar with — a divorced couple with children coming to terms with the husband’s new love and her place in the family. Here, that story is played out by Ed Harris and Susan Sarandon, with Julia Roberts the younger new addition. It’s a story about expectations, adjustments, and a heartwrenching impending death. The New York Daily News said, “It’s a lovely daydream, made lovelier by the fiercely maternal performance of Sarandon as a lioness protecting her cubs, and Julia Roberts as a mass of insecurity trying to measure up to impossible standards.”

Why It Makes Boomers Cry: This more recent art-house film hit close to home for many older moviegoers. It paired Charlotte Rampling and Tom Courtenay as a loving couple soon to celebrate their 45th anniversary. All seems ideal until a letter arrives with the devastating news of the husband’s first love, which will set the film’s unsettling story into motion, a course that will cut to the core.

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