18 Funny Painted Pumpkin Ideas for a Laugh-Filled Halloween

Painting pumpkins is one of those classic fall activities that never gets old. Whether you’re hanging out with friends or just want a goofy touch for your porch, painted pumpkins bring out the laughs.

One to two small pumpkins painted with colorful, funny designs placed on a wooden tabletop with soft natural light.

With these funny painted pumpkin ideas, you’ll have no shortage of ways to bring a little personality to your home this season. Honestly, playful pumpkins are the best way to make your autumn decor feel like, well, you.

Googly Eyes and Goofy Smile

One or two small painted pumpkins with googly eyes and silly smiles on a tabletop.

Big googly eyes and a goofy grin? That’s a painted pumpkin you can’t help but smile at.

Cartoonish Shocked Face

Those wide eyes and open mouth create a funny expression of surprise—perfect for a pumpkin that looks like it just heard spooky gossip.

Clown Face

These pumpkins with big-grinned clown faces with 3D red noses are equal parts funny and creepy—perfect for making guests smile and squirm.

Grumpy Cat

A pumpkin painted with a colorful, detailed cat face featuring blue fur, yellow eyes, and pink ears sits on a sunlit table, with other decorated pumpkins blurred in the background.

Turn a pumpkin into the Internet-famous Grumpy Cat with sharp eyeliner, fur-like paint strokes, and 3D paper or cardboard ears for full sass effect.

Funny Trolls

Close-up of one to two pumpkins painted with bright neon hair designs on a clean tabletop.

Paint your pumpkin with giant cartoon faces, then add neon faux fur above for a Troll look that’ll have kids giggling nonstop.

Diva Face

Close-up of one or two painted pumpkins with cartoon eyebrows on a tabletop.

This smirking pink-cheeked diva with bold brows and lashes is all about attitude—and she knows it.

Laughing Emoji

Paint your pumpkins bright yellow, then top them off with huge laughing emoji faces that are impossible not to love.

Goofy Robot

Bold blocks of blue, yellow, and orange transform your pumpkins into happy little robots straight out of a cartoon.

Dapper Gentleman

Close-up of one or two pumpkins on a table, one painted with a large monocle and wearing a top hat.

For a charming look that says “classy with a side of silly,” paint your pumpkin with a funny face, then top it with a 3D monocle painted blue and a tall hat.

Silly Face With Yarn Hair

Close-up of one to two brightly painted pumpkins on a tabletop, one decorated with colorful yarn hair.

A bright and messy yarn wig, googly eyes, a felt nose, and painted eyebrows and a grin all add personality to a pumpkin face that’s full of chaotic joy.

Toothy Grin

Close-up of one or two pumpkins painted with goofy grins and buck teeth on a tabletop.

Between the giant toothy grin and green paint “hair,” these pumpkins infuse your fall decor with a dash of silliness.

Laughing Ghost

Give your pumpkin a ghostly makeover with a happy face and white body that’s silly, not spooky.

Big Eyes and Big Smile

One to two pumpkins on a table painted with funny smiley faces.

The bright yellow paint, big eyes, and huge grin on this pumpkin prove that sometimes the simple designs are the best—and even the funniest.

Funny School Teacher

Give your pumpkin a quirky school teacher makeover by painting a face with glasses, a tie, and silly features.

Dumbfounded Expression

One or two pumpkins painted with funny dumbfounded cartoon faces on a tabletop with a clean background.

There’s just something about this pumpkin’s dumbfounded expression with bugged-out eyes and a mouth gaping open. You won’t be able to stifle your laugh with a pumpkin that looks this silly.

Happy Bunny

Close-up of one or two pumpkins on a table, painted with a goofy bunny face and whiskers in bright colors.

This cheerful blue bunny design, complete with painted-on whiskers and 3D cardboard ears, is the perfect combo of cute and quirky for your funny pumpkin lineup.

Silly Monster

One to two brightly painted pumpkins with funny monster faces on a tabletop, lit by soft daylight.

Give your pumpkins personality with silly monsters showcasing oversized cartoon eyes, sharp teeth, and splashy dots in bright colors.