I developed a soft spot for McSweeney’s Internet Tendency when I first heard about the site when I was living in Brooklyn in the early 2000s. McSweeney’s had a small store which featured things like taxidermy and a book about how to care for your miniature donkey, and I liked the work they were doing, particularly on their quirky humor site.
I sent them my first submission in 2001, and it was rejected. A couple years later I took a humor writing class through Mediabistro, and was inspired to start submitting to them a little more. I got six more rejections. Then in 2005 my first acceptance — an essay about U2’s song “One Tree Hill” for a series they were running about songs.
Since I had accomplished my goal of getting a piece placed with them, I took a break from submitting there. Life got in the way. Then in 2015 I got back into writing and submitting more regularly. I read their site regularly for a while and then sent them a new piece, and it was rejected. Then I sent a second piece, and it was accepted. It was a piece that poked fun of all the contradictory rules that parents hear about how to discipline toddlers. It was my most successful piece for them thus far (and one of my most successful pieces at any publication) and has helped me get other writing assignments.
I decided to submit again last year, and that piece was also accepted. At this point I felt like I had cracked the McSweeney’s code and would have better luck with acceptances — so of course my next four submissions were rejected. But the fifth one was accepted — a imagined note to a kid’s college roommate about things he never grew out of (e.g. needing to be swaddled at night and sleep in an infant swing).
I still really like the site and will probably submit again. I don’t know that I have cracked the code in terms of acceptances — they can be a tough site to publish in. But reading what they regularly publish and being persistent seem to be the things that have worked for me.