She is best known for her use of unconventional musical instruments, such as the toy piano, and her vintage Victorian Era dresses, as well as her collaborations with the podcast Welcome to Night Vale and musician Jason Webley.

Following this, Rickman grew disheartened from not being able to secure industry attention, and after recording O, You Sinners in Chicago, she decided to "uproot" herself and begin a nomadic stage of her career.

She gave up her home in Los Angeles, and even her beloved cat into the care of friends,[7] to tour and perform at any venue she could secure, including house concerts, to build up a fan base.

Webley had grown interested in an unknown, nearly forgotten woman named Margaret Rucker, who was from his hometown of Everett, Washington, and who wrote poetry and lived a tragic life.

[10] Webley had chosen Rickman in particular due to her love of time-worn things, such as the scrapbook of Margaret Rucker that was found in the bottom of a dumpster by Chicken John Rinaldi.

Since the recording and release of O, You Sinners, Rickman had undergone a great deal of stress and anxiety, resulting in health and neurological issues, from perpetually living on the road,[11] as well as being in an abusive relationship, and misogyny[8] from venue managers and audience members.

"[1] On January 11, 2018, Rickman announced the release of one of her covers, "Riches and Wonders" by The Mountain Goats, performed with Jherek Bischoff,[14] and that she intends to include it on the album;[15] the song was featured as The Weather on the 121st episode of Welcome to Night Vale, "A Story of Love and Horror, Part 1".

"[7][11] For example, her song Pretty Little Head has been called "disconcerting," “borderline childlike," “subliminal peculiarity," and "the feel of a nursery rhyme that’s just starting to teeter off the rails.

[7] The antique Schoenhut was purchased as a piece of furniture, but after growing tired of transporting a large keyboard to and from live performances, she opted to use the toy piano for small-venue shows, which was well received by fans.

[2] Other instruments include the ukulele (which was introduced to her by Jason Webley), accordion, pump organ, singing wine glasses, tambourine, ratchets, children's bells, kazoo, and other noisemakers.

Among the most influential are Siouxsie Sioux, Nick Cave, Andrew Bird,[2] Elton John, The Beatles, Rufus Wainwright, Johnny Cash, Patsy Cline,[1] Joan Baez, Édith Piaf, Kate Bush, Echo & the Bunnymen, Bryan Ferry, and the Cocteau Twins,[7] along with Alfred Hitchcock[1] and Tim Burton[2] as non-musical inspirations.