This month marks the arrival of Dumbo, the first of three remakes from Walt Disney Pictures of its hand-drawn animated classics (Aladdin and The Lion King are arriving this summer). Each of these films boast A-list casts, well-known directors, and big budgets to replicating hand-drawn images via live-action or CG technology.
But they're also based on films with unforgettable songs.
For Dumbo, specifically, its most memorable song is known primarily for being something of a heartbreaker. So with that in mind, grab a box of tissues and let's look at 15 of the saddest songs in Disney history, from Disney and Pixar animation and live-action.
"When You Wish Upon a Star," Pinocchio (1940)
Your mileage may vary, but something about this wistful number always reads as particularly sad to me. Pinocchio, the pinnacle of Disney hand-drawn animation, is one of the studio's most terrifying films. (Just think: a little wooden marionette wants to be a real boy, after which it is sent through a series of trials culminating in being destroyed by a whale. All because he just wants to impress his father!) "When You Wish Upon a Star" plays over the opening credits; decades before it became the studio's theme song, Cliff Edwards' quavery performance makes the song both an ode to the power of dreaming and a haunting piece of music suggesting how sadly unlikely such wishes are to actually come true.
"Baby Mine," Dumbo (1941)
This is the rare Disney song that’s heartbreaking no matter how old you are. The 1941 film that tells the story of a baby elephant with inexplicably large ears that enable it to fly also features one of the most wrenching subplots of parent/child separation. After Mrs. Jumbo lashes out at some jerky humans who taunt her and her son Jumbo, she's locked up in a cage, barely able to swing her baby back and forth in an attempt to comfort him. The song playing over this image, and a montage of other circus animals cuddling with their babies, is "Baby Mine," a truly beautiful lullaby whose sadness is compounded by the protagonist's mother being unable to give her son the love he so badly needs. It's not the first time in Disney history when an animated film was designed to make you sad, but it's still the saddest of all.
"Love is a Song," Bambi (1942)
You may not remember the songs from Bambi as much as you may remember its most memorable moment, in which the mother of young deer Bambi is shot down by an off-screen hunter. But "Love is a Song," which opens the film, is as eerie in its own way as "When You Wish Upon a Star." The number, performed by Irish tenor Donald Novis (best known to theme-park aficionados as an original performer in Disneyland's Golden Horseshoe Revue show), sings of the power and enduring quality of love. However, with the context of what's to come for young Bambi (and who he'll lose), it sounds a lot more heartbreaking.
"Feed the Birds," Mary Poppins (1964)
"Feed the Birds," a song from the 1964 classic Mary Poppins in which the eponymous nanny sings a song to her charges about a homeless birdwoman in London, is famously known as Walt Disney's favorite song in his later years of life. The story goes that he would ask the song's composers, brothers Richard and Robert Sherman, to come into his office and play the song on a whim. It's one of many stone-cold classic numbers from Mary Poppins, yet perhaps the saddest song in the film, in no small part because it's both something of a lullaby and a melodramatic solo with no compare. It's no wonder that, even though Mary Poppins Returns' songs echoed its predecessor often, this song didn't get a parallel in the new film. How could it have measured up?
"My Own Home," The Jungle Book (1967)
Arguably, "My Own Home" is meant to be seductive. It’s sung by a little girl from the "man-village" where the man-cub Mowgli is destined to go. Within the context of the film, we’re meant to think that this song and the girl singing it is enough for Mowgli to leave behind his animalistic days. (Or, if you like, Mowgli encountering this girl is enough to send him right into puberty.) But the point of the song is a little bleak, if not just a little backwards to consider: the nameless girl is fetching water, until she grows up to have a daughter of her own and cooks in her home. It's perhaps not inaccurate to the time period to hear a young woman sing of her life of metaphorical servitude, but no less sad to consider the monotony Mowgli is entering (and the monotony she lives through every day.)
"Not in Nottingham," Robin Hood (1973)
There's a subset of Disney fan that dearly adores this 1973 film, either for its laid-back nature or for its weirdly seductive lead fox characters. (That's not a joke. Google it.) Most of the film's songs were written and performed by country singer Roger Miller, including its sole downer number, "Not in Nottingham." In this song, his rooster character Alan-a-Dale woefully sings about the state of affairs in Nottingham with innocent animals locked up, the Sheriff reigning over all, and things being pretty rough. Of course, Robin Hood eventually saves the day, but this low point is emphasized by Miller's bluesy take.
"Someone’s Waiting for You," The Rescuers (1977)
Though it's far from the best Disney animated film, you could make a solid argument that The Rescuers is perhaps the saddest. Here’s a film in which a little orphaned girl is ruthlessly kidnapped by a prospective jewel thief and her only hope comes in the form of two little mice. The story of poor Penny, and the eponymous characters who save her, has a few songs that play over the soundtrack, and "Someone’s Waiting for You" is the saddest (though, being fair, none of them are terribly upbeat). Each song in the film is melodramatic, but this one lays it on thick and makes it clear how hopeless Penny's plight is (and how lonely a kid in her situation would be). This one's going straight for the tear ducts.
"Candle on the Water," Pete's Dragon (1977)
Pete's Dragon (1977) is largely not a great film, and not well-remembered aside from being fodder for the much better 2016 remake. But the film is a full-scale musical, in the vein of Mary Poppins, combining live-action and animation in depicting the story of a boy and his pet dragon. Most of the songs are as forgettable as the whole film, but at the midpoint, there's "Candle on the Water," a truly underrated piece of music. As sung by Helen Reddy, it's a hopeful but still downbeat ballad performed by a character singing to her lost love. By the end of the film, that lost love returns (in a cop-out moment), but "Candle on the Water" is a hymn of sacrifice and sadness.
"Jack’s Lament," The Nightmare Before Christmas (1993)
The title of this song spells out that it's going to be something of a downer. Early in the Henry Selick-directed stop-motion animated film, Jack Skellington sings of his ennui and disaffection. While he's the Pumpkin King of Halloweentown, Jack has grown bored and dissatisfied, wishing he could find some other joy in his life. The sequence with this song, performed by composer Danny Elfman (who provides Jack's singing voice throughout), features a truly memorable image in which Jack saunters down a spooky forest tendril that spools out in front of him. The song itself is a bit of a dirge, but appropriately downbeat.
"I Will Go Sailing No More," Toy Story (1995)
Just as Toy Story was patient zero for proving the worth of feature-length computer animation, so too was "I Will Go Sailing No More" the test case for one of Pixar's go-to storytelling choices over the last quarter-century. As much as Pixar films are fun, funny, exciting, and more, they're also largely intended to make you cry your eyes out. Toy Story doesn't quite get there, but the Randy Newman song "I Will Go Sailing No More" comes close. The song plays over the soundtrack, performed by Newman, as Buzz Lightyear realizes that the other toys in Andy's room have been telling the truth: he isn't a spaceman, but a toy that can't fly. At the very least, this is a great jumping-off point for future sad Pixar songs.
"Hellfire," The Hunchback of Notre Dame (1996)
This is just generally the most complex villain song in Disney history, if not one of the most complex songs in Disney movies. The form of sadness evinced by "Hellfire" isn't the kind where you feel that bad for the performer — the maniacal Judge Frollo sings the number as he struggles to balance his growing sexual attraction to the comely gypsy Esmeralda. What's sad is less in the character of Frollo than in the mature relatability of a character struggling with desires that can never come to fruition. (Let's also dole out some sympathy for Esmeralda, who's a prop in Frollo's mind for his sexual fantasies.) "Hellfire" deserves all the attention it can get — while this film is not Disney's greatest, its ambition is largely unparalleled.
"You'll Be In My Heart," Tarzan (1999)
It took nearly 60 years for another song in a Disney animated film to mimic the style of "Baby Mine," and all we needed was a songwriter in the form of... Phil Collins! This lullaby is first sung to baby Tarzan by his adoptive mother, a gorilla played by Glenn Close. Close sings the song herself, her voice appropriately tender and even a little shaky as she lets this stranger to her world know that everything will be all right. "You'll Be In My Heart" is not the most lyrically complex song in the Disney discography, but it's a sweet and soulful number, even when performed by Collins himself.
"When She Loved Me," Toy Story 2 (1999)
It's basically impossible to think of a sadder song in a film released by the Walt Disney Company, at least in the modern age. Pixar laid it on exceptionally thick with Randy Newman's "When She Loved Me," which plays over a flashback to the happier time for Jessie the Yodeling Cowgirl (voiced by Joan Cusack) and the girl who loved her and played with her all the time. It's not just that we find out that Jessie was carelessly donated when young Emily grew up and past playing with toys, it's that Sarah McLachlan sings the song, maximizing how many tears you're going to cry out. Thus, "When She Loved Me" is the ASPCA ad of sad songs, specifically designed to make you sad; careful planning aside, it's still a heartbreaker.
"Almost There," The Princess and the Frog (2009)
It's become something of a standard now for songs to get reprised in the films in which they appear, so the version of "Almost There" being called out here wouldn't be the version that you may know best. The song first appears as lead character Tiana explains to her mother that her enterprising, work-hard attitude is close to paying off as she gets enough money to buy her own restaurant in New Orleans of the 1920s, in a gorgeously animated Art-Deco-style number. But later in the film, at a dark moment, Tiana sings an abbreviated version of the song, hinting at how the lyrics and even title to "Almost There" belie the inherent sadness of having to work so hard for your dream only to lose it in an instant.
"Remember Me," Coco (2017)
For Pixar, music is a sure sign of getting the audience to cry. Of course, some of the saddest music in Pixar films has no words at all — just listen to the "Married Life" composition from Up and try not to get teary. Coco was a bit different for Pixar, in that it's the closest thing they've made to an out-and-out musical. Lead character Miguel loves music, even as the rest of his family refuses to support him in his rhythmic desires.
His favorite song, "Remember Me," shows up in a number of contexts in the film: a big, crowd-pleasing production number first, before becoming much sadder by the finale. There, Miguel sings the song to literally encourage his great-grandmother Coco to remember her dead father, who wrote the song as a lullaby to his now-aged daughter. It's, yes, shamelessly manipulative, but no less heartrending to hear the song in this manner.