BOOMER Cartoon Caption Contests: Current and Past

By Brian Marsh | October 3rd, 2022

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 change to create, vote, or just laugh! (Latest update: Oct. 3, 2022)

October 2022 Caption Contest

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


Make us laugh with your caption.


September 2022 Caption Contest

Boomer Cartoon Caption Contest September 2022

Top 10 winners have been chosen – vote for your Top 3!


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 Caption Contest


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

Which winners caught the spirit of this cartoon?


June 2022 Caption Contest

Name that caption June 2022

Check out the winners for the June caption contest.


May 2022 Caption 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 Caption 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 Caption Contest

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

Check out the March winners.


February 2022 Caption Contest

Name That Caption February 2022

Congratulate the winners.


January 2022 Caption Contest

And the winners are …

December 2021 Caption 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 …


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!

More from Boomer