Sometimes Weekly was created by Nick Butler in 2015 to tell the story of Donald Trump threatening to sue him and subsequently cutting him a check. From there, Nick told the story of the time a Lord of Parliament offered him a bribe. In June 2015, Nick recalled his brief Twitter diplomacy with North Korea. In February 2016, Nick created “Don’t Approve This SuperPAC” which the FEC approved. In June 2016, Fox News accidentally advertised a fake Trump dating website Nick created as a joke.

A couple years later, Nick told the story of the time A&E almost filmed a ghost hunting show at his house when he was 14-years old. A few months later, Nick tried to set the dress code for a British secret society after he was emailed by mistake. After a brief hiatus, Nick filed an addendum to Sometimes Weekly with a few short stories that weren’t quite good enough for their own post.

In 2022, Nick apologized to Neill Blomkamp, the director of District 9 for stealing his Twitter handle in 2009, and Neill Blomkamp subsequently accepted the apology.

In 2023, the Sometimes Weekly newsletter launched, Sometimes Weekly, LLC was formed, and the Sometimes Weekly brand expanded to YouTube, podcasts, and Patreon.