Critical response at the time was generally positive and, in retrospective articles, reviewers felt This Side of the Moon helped enhance Cook's musical career.

[12] This Side of the Moon was inspired by Cook's departure from Warner Bros., which she described as her "divorce from Music Row" and a "period of extreme frustration".

"[12] Cook wrote two songs, “Ruthless" and "Heather Are You With Me Tonight", by herself and worked with her then-husband Tim Carroll on "Where the Blue Begins", which they recorded as a duet.

[18] In The Tampa Tribune, Stephen Thompson remarked that the songs had different styles, ranging from a "slow ballad" to a "rollicking mid-tempo number".

[20] Alden described Cook's voice as "high [and] clear", saying it was "reminiscent in its quiet moments of Dolly Parton, or of a more burnished Julie Miller".

[21] Although Thompson noted that Cook lacked a "knockout voice" like Patsy Cline, Kelly Willis and Iris DeMent, he wrote that she had a "sincere, unfussy style of singing".

[26] According to a 2005 press release, Cook planned to embark on a summer tour and perform at the Grand Ole Opry to further support This Side of the Moon.

[30] According to the company's YouTube channel, This Side of the Moon was later licensed to the Orchard Music on behalf of Hog Country Production.

[30] This Side of the Moon's tracks received little airplay,[6] and following the album's release, Cook worked as a waitress to secure a steady salary.

[28] In a 2007 CMT interview, Cook said she developed a fanbase from "a small handful of cult country music fans" that she thought were frustrated with her lack of commercial success; she also mentioned reaching a sense of peace about her experiences with different record deals.

[31] Sanneh included it on his list of 2005's best obscurities,[17] and in an August 2005 article, Thompson named it the best country album by a female artist so far that year.

[3] Describing This Side of the Moon as an improvement over Hey Y'all, Cristiano appreciated how "disappointment obviously didn't dull her artistry".

[21] In 2006, Randall, Carter, and Little also singled out the track when praising Cook for creating "lush harmonies, traditional arrangements, and simple production".

[34] While dismissing the notion that Cook was a guilty pleasure, Cooper praised "Here's to You", "Where the Blue Begins", and "Somebody's Gotta Do It" as "music fit for smiling, humming and other admirable pursuits".

[27] Critics identified the album as an important part of Cook's career,[36][37] such as Louisville's Brent Owen who believed it gave her further exposure in the music industry.

[37] A staff writer for the River Cities' Reader attributed This Side of the Moon and Balls to helping establish Cook as a "soulful country singer and impassioned songwriter".