The band released their breakthrough second studio album, Madison, in 2021, through Saddest Factory Records, an imprint owned by their former bassist Phoebe Bridgers.

[2] As an experiment she wore one suit for an entire year without washing it, vowing to wear it until it "rots off her body" and now intends to eat it.

The band then played South by Southwest on March 16 for the saddestfactory showcase and opened for a few shows on Phoebe Bridgers’ tour in May.

Following the year of touring, Dahl moved to Cerro Gordo, an abandoned mining town in the Owens Valley near Lone Pine, California.

In 2023 Sloppy Jane released a full visual album of Madison featuring eight new music videos to accompany the three already existing ones ("Party Anthem", "Jesus and Your Living Room Floor", and "Wilt").

The film featured Haley Dahl as the Main, and John Ennis as "The Tooth Fairy" (who played the same character in the music video for "Mindy" from the album Willow),[9] along with other uncredited actors and musicians.

In the 2024 film I Saw the TV Glow, Sloppy Jane appeared with Phoebe Bridgers, performing "Claw Machine" in a memorable scene.