The brilliantly funny Bob Mankoff served as cartoon editor for the New Yorker for 20 years, ending in April 2017. Among his other duties he ran the New Yorker Cartoon Caption Contest.
In November 2018, Mankoff launched a similar contest at his new venture, Cartoon Collections. Many New Yorker contest devotees/Mankoff fans immediately started entering the new contest as well.
It isn’t the New Yorker – only the New Yorker is the New Yorker – but it quickly became the second most popular everyone-wants-to-win caption contest.
And … I won the New Yorker caption contest!
Then … I won the Cartoon Collections caption contest!
“The first rule of sex addiction group therapy is to stay on your own couch.”
I feel incredibly lucky and incredibly great to have won both. I am a bit curious if I am the first to do so.
Cartoon Collections allows me up to three entries. I learned by accident to only enter two initially, in case a better one occurs to me later.
That is exactly what happened. I could only think of two captions – and they were not bad, but not great. A couple of days later the winning caption popped into my head. Thank goodness I still had one remaining entry allowed.
Although I thought it was good, I had little hope for this caption, as it is just a bit not-safe-for-work. I don’t think it would have stood a chance in the New Yorker. But Cartoon Collections seems to have a more positive attitude toward slightly naughty humor. This is, I think, the first naughty joke to win. Also possibly the longest. Shorter is generally funnier, but the key rule is no wasted words.
