BOOMER Cartoon Caption Contests: Newest and Beyond

By Brian Marsh | June 2nd, 2025

A new chance every month to exercise your sense of humor ... or judge someone else's!

Every month, the Boomer caption contest provides a new cartoon for readers to write their own clever caption. We also capture the top 10 caption submissions so readers can vote for their favorite. And we announce the winner from the cartoon before that!

This page is updated monthly with new cartoons, so bookmark it for your chance to create, vote, or just laugh! (Latest update: June 2, 2025)

June 2025

Snake getting a tattoo with the artist poised to begin. Think you’re funny? Enter our contest to pit your wits against others or see the winners in Boomer’s Name That Cartoon CaptionSend us your best ink for this caption.

 

May 2025

Cartoon of snow woman melting with a human woman looking on, For Boomer magazine Name That Cartoon Caption contest May 2025Vote on your favorites among the Top 10 captions.

 

April 2025 Cartoon

Two monkeys playing on a playground set, with a mug of beer and a bowl of nuts. For the Boomer name that cartoon caption contest, April 2025Cheers to this month’s swinging winners!

 

March 2025 Cartoon

Name That Cartoon Caption: March 2025 - A teacher in a red jacket hugs and gnaws on a log lying in the waterHey, you eager beavers, the results are in!

 

February 2025 Cartoon

A cartoon showing an angry adult female landline phone talking to a huffy young smartphone. For Boomer Name That Caption Contest February 2025See which captions rang up the most votes – for a Boomer caption contest novelty, a three-way tie for first place!

 

January 2025 Cartoon

Cartoon of two women looking at a potted rose plant wearing a physician's uniform / costume. For Name that cartoon caption contest January 2025

See which caption grew the most votes.

 

December 2024 Cartoon

Two onions at home watching a cooking show on TV as a chef begins to slice an onion. For the Boomer cartoon caption contest December 2024

And the winners are…! 

 

November 2024 Cartoon

A cartoon of a dog drumming as a busker on the sidewalk as a couple in the background looks on. For the Boomer Name that cartoon caption contest, November 2024See whose captions were music to our ears.

 

October 2024 Cartoon

Cartoon image of three bears dressed for an evening at a night club. For Boomer Cartoon Caption Contests October 2024
See whose captions prevailed.

 

September 2024 CartoonFor the Boomer September 2024 cartoon caption contest: a manatee bumps his nose into the ocean floor as two fish journalists report his fall

See who won the ‘Pool-itzer’ prize for their captions.

 

August 2024 Cartoon

Name That Cartoon Caption: August 2024

See who walked away with the win.

 

July 2024 Cartoon

See whose captions turned heads!

 

June 2024 Cartoon

Boomer Caption Contest: June 2024. Three thieves dressed in black, one like a nutcracker doll, are trying to open a safe.See who stole the Top 3.

 

May 2024 Cartoon

A cow dressed in rastafarian clothes standing on two legs and drinking milk. For the may cartoon caption contest in Boomer magazine

See whose captions moo-ved the voters.

 

April 2024

Boomer’s Name That Caption: April 2024 - costumed dog digging up street. Full size height

See who dug up a win in the April contest.

 

March 2024 Caption Contest

Two pirates, one applying anti-gray cream to his mustache and beard, for the Boomer Name That Caption Contest March 2024

See which captions conquered!

 

February 2024 Caption Contest

Two pigeons in nice clothes chatting in a business office while a suit-clad cat stalks them. For Boomer cartoon caption contest February 2024

The Top 10 are poised for your vote.

 

January 2024 Caption Contest

A boy fencing with an English Literature book, with swords. For Boomer caption contest, January 2024

See whose captions came out on top.

 

December 2023 Caption Contest

cartoon of a Hotwheels car with people on a Hotwheels track, for Name That Caption December 2023

See whose caption reached the top.

 

November 2023 Caption Contest

See whose captions won.

 

October 2023 Caption Contest

cartoon of two dressed up winged bugs dining out, ordering from a buggy waiter. By Brian Marsh

Didja hear the buzz? Tied votes = more winning captions!

 

September 2023 Caption Contest

two ghost-like gentlemen at a bar, toasting, while women run away in the background. Boomer name that caption: September 2023

See whose captions were outta this world!

 

August 2023 Caption Contest

Think you’re funny? Enter our caption contest and pit your wits against others or see the winners in Boomer’s Name That Caption: August 2023

See who won … with a tie giving us four winners this month! 

 

July 2023 Caption Contest

crow and scarecrow having coffee together. For Name That Caption: July 2023 in Boomer Magazine online

Don’t be scared … see which captions won this month.

 

June 2023 Caption Contest

A mole on the Earth's moon for the Boomer June 2023 cartoon caption contest

See who landed the top three captions.

 

May 2023 Caption Contest

Two ancient Romans surrounded by Roman buildings with a volcano spewing confetti in the background. For the May 2023 Caption Contest in Boomer magazine.

See the winners, whose explosively funny captions got the most votes.

 

April 2023 Caption Contest

An eel "in line" at the SeaMV with two fish behind him. Boomer cartoon caption contest April 2023

See who made it to the front of the line!

 

March 2023 Caption Contest

Name That Caption for March 2023, two fishermen in a boat with a mermaid beneath

See who landed the winning captions.

 

February 2023 Caption Contest

See who gobbled up the votes.

 

January 2023 Caption Contest

January 2023 Boomer cartoon caption contest - woodchuck kicking a tree

We had to chuck all but the top three. See who won! 

 

December 2022 Caption Contest

See who scored in the December contest.

 

November 2022 Caption Contest

cartoon for contest to name caption November 2022: human-sized candy corn sitting at a lawyer's desk

See whose sweet and corny caption captured the most votes..

 

October 2022 Caption Contest

A cow pole vaulting in a crowded sports stadium. The Caption Contest October 2022

See who moooved our readers to laughter!

 

September 2022 Caption Contest

Boomer Cartoon Caption Contest September 2022

See who won!!

 

August 2022 Caption Contest

 

two men at an office water cooler with the boss camel in his office

See whose dry humor triumphed this time.

 

July 2022 Contest

 

Boomer Caption contest July 2022 - boogie boy in parents' bedroom

Which winners caught the spirit of this cartoon?

 

June 2022 Contest

Name that caption June 2022

Check out the winners for the June caption contest.

 

May 2022 Contest

May 2022 Boomer Cartoon Caption Contest - "ice cream" truck with gas pump handles in the cones

Check out this month’s winning captions.

 

April 2022 Contest

Name That Caption: April 2022 - two crazy dinosaurs behind a mountain landscape while a woman paints in the foreground

See the winners of this caption contest.

 

March 2022 Contest

Cartoon caption contest: March 2022 - two dogs fencing on a stage with the owners looking on

Check out the March winners.

 

February 2022 Contest

Name That Caption February 2022

Congratulate the winners.

 

January 2022 Contest

And the winners are …

December 2021 Contest

Name That Caption December 2021 - cartoon of two boys looking at the moon, with the moon as a person's face, crying

See who’s funny

November 2021 Boomer Caption Contest

Cartoon of a dad and child on a beach with someone selling seashells. Name That Caption November 2021

The winners are in!

October 2021 Boomer Caption Contest

Caption contest CUCUMBER

See which captions won!

September 2021 Boomer Caption Contest

Caption contest ducks

See who the winners were!

August 2021 Boomer Caption Contest

Taco Tuesday babyyy

Who’s funny?!

July 2021 Boomer Caption Contest

King Lion

Will the winners make you laugh?

June 2021 Boomer Caption Contest

Caption contest GOAT

Winning captions.

May 2021 Boomer Caption Contest

Pancakes caption contest

See who won!

April 2021 Contest

Baby caption contest cartoon

Does the April caption make you laugh?

March 2021 contest winners

Caption contest

Who was funniest?

Who delivered the best caption in February 2021?

FedEx Godmother cartoon

Check out the winning caption.

See who was tops among the January 2021 entries …

Gargoyle

See who won!

Laugh at the previous winners, including …

December 2020:

Broke caption contest

November 2020:
Caption Contest dog!

Congratulations to all our winners!

Get some tips on writing humorous captions from comedian Joe Toplyn.

Like nostalgia? Browse celebrity nostalgia on our website.

Or sign up for our monthly Nostalgia e-newsletter or other e-newsletters tailored for boomers!

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