The album was originally to be released by Columbia Records, but they dropped the project in October 2011 after finding the music was more mature than they anticipated, and S-Curve later picked it up.

American singer-songwriter Nikki Jean was best known as a featuring artist on the 2007 album Lupe Fiasco's The Cool and its single "Hip Hop Saved My Life".

She described herself to journalist Jim Fusilli as an "unlikely candidate" to carry out the concept but believed that her lack of success allowed her to approach each writer as a fan who wanted to learn from them.

Hollander contacted Paul Williams and Carole King, while Jody Gerson reached out to songwriters such as Burt Bacharach and Lamont Dozier.

However, when he received the demos, Hollander felt that some of their co-writers were attempting to emulate "current rhythmic shit without having much, if any, understanding of the Black Eyed Peas and T Pain [sic] ruling radio at the time."

[2][4] This resulted in "Steel and Feathers (Don't Ever)"—the song was originally written for Shot of Love (1981) but had been left unfinished until Jean worked on it, quickly earning Dylan's approval.

[9] "Mercy of Love" was written by Jean and the songwriting couple Barry Mann and Cynthia Weil; it is a ballad which combines '60s girl-group music and modern pop.

[9] Jean promoted Pennies in a Jar through appearances on the Late Show with David Letterman, Tavis Smiley, Weekend Edition Saturday and Live from Daryl's House.

This was easily the biggest miss of my career, and man, it stung.Despite its poor commercial performance, Pennies in a Jar received positive reviews from music journalists.

AllMusic's Andy Kellman said that the album was "very easy to enjoy, voiced by a remarkably refined artist who is neither squarely R&B nor pop", considering Jean a worthy songwriter and the songs' composition "appropriately classicist".

[8] Jim Fusilli of The Wall Street Journal wrote that she "sings with warmth and sincerity, and while many of the compositions bring to mind the work of her famous counterparts, she's in there too.

"[1] Billboard's review opined that Jean "[excelled] when she plays into her collaborators’ strengths", praising the production and arrangements as "sounding breezy and simple, yet [it was] far more accomplished than most modern R&B".