WHEN IT COMES TO THE SPOOKIEST NIGHT OF THE YEAR, ARTISTIC INTERPRETATIONS RANGE FROM THE DELIGHTFUL TO THE TERRIFYING, AS SEEN IN THESE PAST AND PRESENT HERITAGE LOTS
By Rhonda Reinhart | October 21, 2025
Be it magazine covers and comic books or movie posters for horror classics, generations of artists have taken a variety of approaches to depicting Halloween. Depending on the artwork, witches, ghosts, and goblins can be spine-chilling or utterly charming – or something in between. Even a simple jack-o’-lantern, depending on who wields the paintbrush, can instill fear or bring a smile.
In celebration of the holiday, we’ve rounded up nine Halloween-themed works from past and present Heritage auctions, including nostalgic illustrations, playful animation, and paintings made to fright. Keep reading – if you dare – to see more.
Set against the backdrop of a rural starry night, the grinning kids in Eugene Iverd’s Halloween Smiles are lit from the glow of the jack-o’-lantern they are proudly setting up. The guileless image graced the Halloween 1934 cover of The Saturday Evening Post and stands as one of Iverd’s most delightful depictions of the ideal American childhood, which was his signature subject. The quality, emotion, and nostalgic joy of this work make it a classic example of everything collectors love about cover art from The Saturday Evening Post. The oil-on-canvas painting is available in Heritage’s November 4 Illustration Art Signature® Auction.
Though the central figures remained the same (two costumed kiddos and a carved pumpkin), the 1935 Halloween cover of The Saturday Evening Post traded festive for frightful. In Halloween Scare, Frederic Stanley’s take on the ooky-spooky holiday, something must have gone bump in the night because the smiling faces of Eugene Iverd’s subjects are long gone, replaced instead with fearful expressions, complete with wide eyes and gaped mouths. Stanley’s Halloween painting sold for $56,250 in a May 2015 Heritage auction.
Forty-three years after Frederic Stanley took a stab at a Halloween scare for The Saturday Evening Post, Robert Gleason catapulted the concept to a whole new level when he created the instantly recognizable poster art for John Carpenter’s Halloween. The 1978 slasher flick forever changed the horror landscape, and Gleason’s artwork for the film’s original one-sheet remains one of the most iconic images in scary-movie history. Though the painting’s components seem simple at first glance – a creepy combination of a hand, a knife, and a pumpkin – Gleason noted in 2016 that there is more there than meets the eye: “While painting the hand, my thought was to have dramatic light and dark shapes to match the strobe stabbing effect of the pumpkin. I did not consciously know that I was infusing in the back of the hand a screaming monster with worms coming out of his mouth, eye, and nose. I couldn’t have done it better if I had tried to do that. What dark nightmares lurk in my psyche?” Gleason’s original painting for the poster sold for $83,650 in a March 2016 Heritage auction.
Animator Bill Melendez is best known for his work on more than 50 animated Peanuts television specials, including the Halloween favorite It’s the Great Pumpkin, Charlie Brown. In the 1966 classic, as the gang prepares for an evening of trick-or-treating, Lucy utters this ironic advice before donning a witch’s hat and mask: “A person should always choose a costume which is in direct contrast to her own personality.” This hand-inked and hand-painted production cel featuring Lucy dressed as a witch sold for $11,400 in an October 2023 Heritage auction.
Only Charles Addams’ second Halloween-themed cartoon to appear in The New Yorker, this work is one of the rare early published pieces that show the development of his now-classic Addams Family sensibility. The gag, captioned “She shows up every Halloween,” shows a black-hatted witch with a shock of white hair stirring a cauldron in a fine dining kitchen, surrounded by a bemused staff. It’s a significant offering by the legendary cartoonist, who would go on to develop this archetype into the Addams Family’s Granny Frump. The work is available in Heritage’s November 4 Illustration Art Signature® Auction.
The first issue of Donald Duck – a comic-book offshoot of Four Color Comics – debuted in 1952 with a Halloween-themed cover by cartoonist Carl Barks. Based on the short story “Trick or Treat,” the cover shows Donald opening the door to a menacing Witch Hazel, who is accompanied by costumed versions of Huey, Dewey, and Louie. Two decades later, Barks revisited the concept with his painting Halloween in Duckburg, but this time he amped up the whimsy, adding four mischievous monsters, a pink skeleton, and a flying jack-o’-lantern. The bewitching artwork sold for $83,650 in an August 2011 Heritage auction.
Tim Sale
Released in October 1995, Batman Ghosts finds Batman being awakened by a maniacal laugh coming from downstairs of Wayne Manor. There he discovers his friend and guardian Alfred Pennyworth tied up at the hands of Joker. The Dickensian story, in which Bruce Wayne meets the Ghost of Halloween Past, the Ghost of Halloween Present, and the Ghost of Halloween Future, comes from the iconic team of writer Jeph Loeb and artist Tim Sale. Sale’s original art for Pages 34 and 35 of Batman Ghosts sold for $43,200 in a June 2022 Heritage auction.
Sean Cliver is a man of many talents. In addition to serving as a producer and writer for the Jackass TV series and movies, he is a longtime skateboard artist who got his start as a designer for Powell-Peralta in 1989. He has even written two books on the topic – Disposable: A History of Skateboard Art and The Disposable Skateboard Bible. In 2008, Cliver, long known for his irreverent and politically incorrect creations, joined forces with the skate brand Supreme, contributing his original artwork to a series of boundary-pushing skateboard decks. The collab included works dubbed Motel Hell and Halloween, the latter a veritable buffet of problematic costumes. Both decks are available in Heritage’s October 30 Urban Art Signature® Auction.
Florence Pearl England Nosworthy
Halloween Spirits, Hearth and Home magazine cover, October 1930
Depictions of kids’ Halloween costumes were a little more wholesome in 1930, as evidenced by this sweet watercolor painting by Florence Pearl England Nosworthy, who created the image for the October cover of Hearth and Home magazine. Here, a rosy-cheeked little girl in an orange sash and witch’s hat admires herself in a handheld mirror while her pet cat, also in costume, looks on. Pumpkins, bats, and a flickering candle round out the charming Halloween scene. The artwork sold for $4,687 in an April 2019 Heritage auction.
