Allmusic describes their body of work as containing "sadness, paranoia, misery, and dry humor", comparing them to AJJ or 'a sarcastic Bright Eyes'.

[1] Clayton enlisted drummer Dan Watson to turn Crywank into a band for their third full length, Tomorrow Is Nearly Yesterday and Everyday Is Stupid which was self-released in 2013.

Crywank released the tongue-in-cheek Shameless Valentines Money Grab EP in time for the holiday in 2014.

A few weeks later, Clayton also released a Simpsons-inspired EP, Following the Lizard Queen, from the perspective (and under the name) of Langdon Alger, a minor character from the show.

[15][16] In March 2022 Crywank ended their hiatus and continued their postponed farewell world tour, doing shows around Canada with COMMUTED, Guard Petal and Jordaan Mason.

[18] In May 2023, Crywank toured the United States on three headline tours with support from Absinthe Father, Foot ox and local news legend and as a supporting band with Brighton-based indie rock band Lovejoy, as well as releasing a single titled Don't Listen to This Song featuring Guard Petal.

In February 2024, Clayton announced on the Crywank X page that the band was not breaking up, despite their previous farewell tour, and would be bringing in a new member, bass player Jules from Guard Petal.

[20] Between May 3rd and May 4th 2024, Crywank attempted to set an unofficial world record for the most gigs played in different cities in 24 hours.