Entertainment
Ranking The 17 '90s Movies That Made You Cry — How Many Tears Did You Shed?
If you're watching any of these '90s movies, be prepared to stock up on the Kleenex. These '90s flicks are guaranteed to make you sob into your popcorn, though just how much depends on which film you put in the DVD player. Check out our list of the '90s movies that will have your eyes working overtime, ranked from "misty-eyed" to "full-out cry fest." (Warning: Spoilers to follow.)
#17 '10 Things I Hate About You' (1999)
What It’s About: In this modern adaptation of Shakespeare’s The Taming of the Shrew, Cameron (Joseph Gordon-Levitt) must find a prom date for Kat (Julia Stiles) so he can take Bianca (Larisa Oleynik) to the prom, which he does in bad boy Patrick (Heath Ledger.)
Why It’s Sad: It’s not sad at all until the end of the film, when Kat recites her love poem to Patrick and breaks down in tears in front of the whole class. You have no soul if that doesn’t make you well up a bit. Luckily, the film ends the way it begins — on a very happy note.
Image: Buena Vista Pictures
#16 'Good Will Hunting' (1997)
What It’s About: A troubled janitor at M.I.T. with a brilliant mathematical mind learns how to deal with his past demons from his new therapist.
Why It’s Sad: The film is more gut-wrenching than weep-inducing, but you may want to keep a tissue in your pocket just in case the breakup scene between Will (Matt Damon) and Skylar (Minnie Driver) is too tough to bear. You’ll also get misty eyed at the film’s bittersweet ending, which involves Will “going to see about a girl.”
Image: Miramax Films
#15 'The Sixth Sense' (1999)
What It’s About: A boy (Haley Joel Osment) sees dead people. His psychiatrist Malcolm (Bruce Willis) helps him deal.
Why It’s Sad: Though the rest of the film is a supernatural thriller through and through, the ending will make you feel all the feels. M. Night Shyamalan’s reveal that Malcolm was a ghost the entire time wasn’t just shocking, it was extremely sad — Malcolm finally realizes that the perceived tension between him and his wife is actually just her coping with the grief of losing him. He finally tells her that he loves her and “moves on.”
Image: Buena Vista Pictures
#14 'The Lion King' (1994)
What It’s About: A lion returns to his pride to claim the throne that was stolen from him by his murderous uncle years earlier.
Why It’s Sad: Mufasa’s death scarred 90s kids for life. The fact that it’s an animated movie softened the blow, but not by very much.
Image: Buena Vista Pictures
#13 'Forrest Gump' (1994)
What It’s About: Forrest (Tom Hanks) is an average man who does extraordinary things (usually by accident) that change history forever.
Why It’s Sad: It’s a long, life-spanning movie, and while there are plenty of happy moments, you’ll definitely shed a tear whenever someone dies. There are at least three deaths, so bring a few tissues.
Image: Paramount Pictures
#11 'Edward Scissorhands' (1990)
What It’s About: A man with scissors for hands (Johnny Depp) is taken in by a kind family but is soon run out of town due to fear and jealousy from the community.
Why It’s Sad: Edward is a kind soul wrongfully ostracized by small minded people, and the whole thing just really, really sucks. You’ll feel a slight sense of melancholy throughout the entire movie, but the tears will well up when it’s revealed the Edward still makes snow for a now-elderly Kim, his one-time love.
Image: 20th Century Fox
#10 'The Truman Show' (1998)
What It’s About: A man (Jim Carrey) finally learns that his entire life has been a long-form reality series.
Why It’s Sad: Most of the film is thought-provoking, not sad, but it ranks on this list because the ending is such a doozy. The ending of The Truman Show — in which Truman asks the creator of the series whether anything in his life was real — is bittersweet and will definitely get those tear ducts working.
Image: Paramount Pictures
#9 'American Beauty' (1999)
What It’s About: Lester (Kevin Spacey) is having a mid-life crisis while everyone else in his world are having problems of their own.
Why It’s Sad: As American Beauty explains, you don’t know what’s good in life until it almost slips from your fingers. The film’s shocking ending — Lester is killed — is met with a sweet, very sad monologue from our narrator that will make you shed a tear or five.
Image: DreamWorks Pictures
#8 'Ghost' (1990)
What It’s About: A murdered man (Patrick Swayze) must find a way to protect his girlfriend (Demi Moore) from beyond the grave.
Why It’s Sad: Because ghosts eventually have to move on, even if they are in love. It would rank higher, but at least Whoopi Goldberg is around for comic relief.
Image: Paramount Pictures
#7 'The Shawshank Redemption' (1994)
What It’s About: Andy (Tim Robbins), a man who had been wrongfully convicted. but never loses hope that he’ll get out.
Why It’s Sad: There’s an overwhelming feeling of hopelessness for the majority of the film, despite Andy’s hope for the future — things really, really suck for Andy for about two and a half hours of the movie. It would rank much higher on the list if the last 15 minutes weren’t so optimistic — you’ll weep tears of joy at the end of this one.
Image: Columbia Pictures
#6 'Armageddon' (1998)
What It’s About: A group of drillers must detonate a bomb to destroy the asteroid headed for Earth.
Why It’s Sad: It’s one of the few disaster movies that ends with a very personal death. Henry (Bruce Willis) sacrifices himself so that A.J. (Ben Affleck) can live and marry Henry’s daughter, Grace (Liv Tyler). Cue the Aerosmith and the weeping.
Image: Buena Vista Pictures
#5 'Boyz n The Hood' (1991)
What It’s About: A group of boys grow up on the rough streets of South Central L.A.
Why It’s Sad: Yes, there is death in the film, but what makes Boys n The Hood so tragic is that it’s almost seen as an inevitable part of growing up in the neighborhood. Ricky’s death is particularly crushing as he’s seen having scored a scholarship to USC just hours before his onscreen murder. You’ll cry for Ricky, but the rest of the film really should just make you mad — because in many ways, that was the filmmaker’s intention.
Image: Columbia Pictures
#4 'Titanic' (1997)
What It’s About: High-society girl Rose (Kate Winslet) falls for poor boy Jack (Leonardo DiCaprio) on the ill-fated Titanic.
Why It’s Sad: “I’ll never let go, Jack!” — spoken by Rose, as she lets Jack’s dead body float to the bottom of the Atlantic. The only thing stopping Titanic from ranking higher on the sad scale.
Image: Paramount Pictures
#3 'Stepmom' (1998)
What It’s About: Jackie (Susan Sarandon) is uneasy about the role that her children’s future stepmother Isabel (Julia Roberts) will play in their lives.
Why It’s Sad: Jackie is diagnosed with terminal cancer and essentially gives Isabel her blessing to help raise her children. It is so, so sad, but might rank higher if there was no peace between the two moms of the film.
Image: Columbia Pictures
#2 'Philadelphia' (1993)
What It’s About: Beckett (Tom Hanks) sues his law firm for wrongful termination after he is discriminated against for contracting HIV.
Why It’s Sad: Watching Beckett die from AIDS related causes is awful, and so is the way he is treated for having the disease. It’s really just melancholy all around, but at least there’s a somewhat uplifting message about the dangerous of discrimination. (And Beckett does, in fact, win his case.)
Image: TriStar Pictures
#1 'My Girl' (1991)
What It’s About: Young Vada (Anna Chlumsky) deals with the struggles of adolescence and her first crush on neighborhood kid Thomas (Macaulay Culkin).
Why It’s Sad: Thomas dies of a bee sting that he gets after looking for Vada’s mood ring. And it is the most depressing thing ever.
Image: Columbia Pictures
