25 Awesome Funny Pumpkin Designs

We curated 25 of the very best awesome funny pumpkin designs so you can pick one and start carving in minutes.

1. Plain Thumbs Up Relief
The classic thumbs-up hand, thumb raised high over four curled fingers, presented as a bold etched panel on the pumpkin's face. No holes are pierced; you shave the outer skin inside the hand outline so the pale flesh forms the gesture, leaving thin rind lines to separate the fingers. Keep the shaved depth even and stop at each finger line so the knuckle ridges stay dark and readable.
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2. Split Tooth and Two Sparkles
A giant molar with a split between its two roots gleams at the center, flanked by a four-point sparkle on each side and two small dot accents. The tooth outline is cut through around its lobed crown and twin roots, and the sparkles and dots are pierced as well, making a bright emblem any dentist would love. At medium difficulty, the pinch between the roots is the tightest cut, so saw into that notch from both sides and go slow.
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3. Sleepy Eyes and Eight Lashes
Two closed crescent eyes with four little lashes apiece rest above a small oval mouth, while round dots on each side form rosy cheeks for a sweetly sleeping face. Every crescent, lash, dot, and the mouth is pierced through, so the tiny lash cuts do the expressive work. Cut the two big crescents first, then add the short lash strokes with a fine saw, keeping each one clear of its neighbor.
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4. Wink and Five Rounded Gaps
One eye is a jaunty upswept crescent wink while the other stays a wide triangle, set over a small diamond nose and a lopsided grin broken into five rounded gaps by chunky teeth. The eyes, nose, and mouth gaps are cut through, leaving the tooth shapes as attached skin between them. A medium carver should cut the five mouth gaps individually rather than one big mouth, which keeps every tooth solidly connected and the crooked smile intact.
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5. Winking Seven-Tooth Grin
A goofy winking jack-o'-lantern with one wide round eye, one squinting wink, a triangle nose, and an enormous grin broken up by a jumble of square and pointed teeth along both lips. Every feature is cut clean through so the mismatched expression beams from the whole face. At medium difficulty the mouth is the main event; cut the grin outline first, then shape each tooth individually, alternating sides so the lip strips stay supported.
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6. Cyclops Eye and Five Teeth
A goofy cyclops with one giant round eye under a curly brow, a small triangle nose, freckle dots on each cheek, and a huge laughing mouth with five stubby teeth. The features are cut through, and the pupil stays in place as an attached tab hanging inside the enormous eye. That pupil bridge is the medium-level test; cut both sides of the tab before freeing the rest of the eye circle.
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7. Wink and Barred Square Grin
One huge round eye stares while the other squeezes into a curled wink above a giant open grin packed with blocky square teeth, and freckle dots sprinkle each cheek. The eyes, mouth, and freckles all cut through the wall, with skin bridges left in place to form the teeth. Cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block stays anchored.
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8. Crossed Eyes and Buck Teeth
Huge crossed googly eyes sit under raised brow slots while a gaping oval mouth shows off two goofy buck teeth, with freckle dots on each cheek. The eyes, brows, mouth, and dots are all pierced through, and the dark pupils and teeth are rind left attached inside the openings. Those attached pupils and teeth are the tricky bit; cut around them slowly and leave their connecting bridges generously wide.
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9. Teardrop Eyes and Three Stars
Two enormous teardrop eyes dominate this quirky alien mug, floating above a tiny triangle nose and a crooked grin made of separate oval mouth slots, with three little stars sprinkled around the face. Every eye, slot, and star is cut through, giving the pumpkin a goofy otherworldly stare. At medium difficulty, carve the huge eyes last since removing that much wall weakens the face, and keep the small oval grin slots evenly spaced.
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10. Raised Brows and Four Tears
A theatrically miserable pumpkin with worried brows arched high, drooping oval eyes, four teardrops sliding down the cheeks, and a deep downturned frown showing a hint of teeth. Every brow, eye, tear, and the big frown is cut through so the whole sob story glows. A medium carve that lands the joke best when the tears line up; cut the small teardrops first, then the eyes, saving the wide mouth for the end.
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11. Wide Eyes and Eight Cheek Dots
Raised eyebrow slivers arc over two huge oval eyes, while a big O shaped mouth gasps below and four round dots freckle each cheek. All the openings are simple pierced shapes, but their sheer number bumps this into medium territory. Drill or core the eight cheek dots first while the wall is still strong, then cut the large eyes and mouth so the face keeps its comic shocked stare.
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12. Unequal Eyes and Crooked Teeth
This lovably lopsided face pairs one round eye with one droopy crescent eye, a triangle nose, and a huge crooked grin full of uneven square teeth, plus a pair of dot dimples on each cheek. The eyes, nose, mouth, and dots are pierced while the mismatched tooth bars stay attached. It suits odd-shaped pumpkins perfectly; cut the tooth gaps in random sizes and the wonkier it looks, the better.
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13. Lovestruck Heart Eyes Face
This lovestruck face beams with two big heart-shaped eyes under curved brows, a wide open smile showing three square teeth, and playful dot dimples on each cheek. All the features are cut through the wall, so the hearts glow brightest and instantly read as the classic heart-eyes expression. Cut the notch at the top of each heart carefully with short strokes, since that little dip is what makes the shape.
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14. Barred Eyes and Cheek Tears
A goofy clown face with big round eyes crossed by horizontal rind bars, teardrop shapes dangling from each cheek, a button nose, and a huge grin with three chunky teeth. The eyes, tears, nose, and mouth are all cut through, while the eye bars and teeth stay as attached rind bridges. Those bars make it a medium carve: cut each eye as an upper and lower opening on either side of the bar, supporting the bridge with a finger as you finish the strokes.
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15. Three Eyes and Rounded Teeth
Three round eyes line up across the brow of this cheerful monster, above a wide grinning mouth with four rounded teeth hanging from the top lip and a small diamond accent cut on each cheek. The eyes, diamonds, and mouth are cut through, with the teeth left attached to the upper mouth edge. At medium difficulty, the main care point is those hanging teeth: cut around each one gently, and try it on a green or warty pumpkin for extra monster energy.
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16. Three Eyes and Four Teeth
Three round eyes of different sizes line up above a small rectangular nose and a wavy grin broken by four square teeth, giving this mutant jack-o'-lantern a delightfully goofy personality. The eyes, nose, and mouth are all cut through, with the teeth left as tabs, and tiny freckle dots may be etched shallow on the cheeks. A medium carve mainly for tooth care; cut into the grin from between the teeth so each square tab keeps its corners.
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17. Left Wink and Six Cheek Wedges
A playful winking jack-o'-lantern: one big round open eye, one arched wink, a triangle nose, and a smiling mouth with blocky teeth, all framed by three thin whisker-like wedges slashed across each cheek. Every opening is cut through, and the six cheek wedges throw extra slivers of light. At medium difficulty, cut the large features first and finish with the skinny cheek slits, using a fine saw so each wedge tapers to a clean point.
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18. Almond Eyes and Wide Cat Smile
A sly cat face with two swooping almond eyes, a small triangle nose, and an enormous curling grin that stretches nearly ear to ear. The eyes, nose, and mouth are cut fully through, and the thin rind strips inside the smile create the mischievous cat-lip curves. At medium difficulty, the tapering eye points need patience; finish each point with a short pull cut toward the corner.
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19. Die and Pawn on Curved Board
A six-sided die and a classic rounded game pawn sit side by side on a curved, segmented game board path. The die faces, pawn silhouette, and board track are shave-carved so they glow in warm relief, with the pips scooped deeper for contrast; nothing pierces the wall. Shade the two big shapes first, then dot in the pips with a small round gouge, keeping each one the same depth so the die reads evenly.
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20. Margarita and Citrus Wheel
A wide-rimmed margarita glass on a slender stem, garnished with a citrus wheel notched onto the rim, its segments radiating like a tiny sun. This is a shading design: the glass, stem, and fruit are shaved to different depths so the salt-rimmed bowl reads brighter than the stem. Etch the citrus wheel's thin segment lines with a V-tool after the broad shapes are done so they stay crisp.
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21. Seated Capybara with Smile
The internet's favorite chill rodent sits in calm profile, its whole rounded body glowing warmly with a small dark eye and nostril left as untouched spots of skin. Rather than piercing the wall, you shave the capybara's full silhouette down to the inner flesh so it lights up as one soft shape. For this medium shading carve, peel the big body areas with a flat scraper, thin them evenly, and leave the eye and nose dots strictly alone.
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22. Frothy Four-Panel Beer Mug
A frothy beer mug fills the pumpkin, its billowing head of foam spilling over a four-panel glass body and a sturdy curved handle. This is a shaded design carved into a continuous wall, so the mug is shaved out of the skin rather than pierced, which keeps the foam bubbles and panel lines intact. Shave the foam shallow and fluffy, then go slightly deeper on the four panels so the glass glows brighter than the head.
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23. Round-Eyed Clown With Brows
A cheerful clown face with raised curving brows, big round eyes, a round button nose, small dot cheeks, and a huge sweeping smile. Every feature is a straightforward cut-through opening, and the little cheek dots on each side add extra sparkle at night. At medium difficulty the challenge is spacing: transfer the stencil carefully so the brows sit clear of the eyes, then drill the small dots with a pumpkin drill or apple corer for perfect circles.
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24. Seven-Leaflet Cannabis Leaf
A symmetrical seven-leaflet cannabis leaf spread across the pumpkin's face, each serrated blade radiating from a short central stem. The leaf glows through shaved skin rather than open holes, so every jagged tooth along the edges reads clearly while the wall stays solid. A medium shading design; score the full outline first, then peel from the center of each leaflet outward so the serrations do not tear. Best saved for the adults-only party pumpkin.
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25. Fishbone Skeleton
A cartoon fish skeleton stretches across the pumpkin, complete with an open-mouthed head, a round eye, a long spine lined with curved rib bones, and a fanned tail. The whole design is skin-shaved rather than pierced, so the pale bones glow softly against the dark rind like an x-ray. For this medium etch, outline the spine first, then shave each rib in one smooth stroke so the curves stay parallel and evenly spaced.
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