[2][3][4] It was slated to be supported by the Southside Summer Tour 2020, which would have featured guests Kip Moore, Travis Denning, Brandi Cyrus, and Ernest, and was set to begin in Charlotte, North Carolina, on May 28, 2020, but was canceled due to the COVID-19 pandemic.

[18] Writing for Rolling Stone, Jon Freeman highlighted the "thread of sensitivity" in Southside and opined that the album made Hunt "a crossover star.

[26] In concurrence, Pitchfork's Natalie Weiner stated that the album "shows a clarity of purpose that his debut lacked" while also praising Hunt's "enviably organic" way of threading "the country/hip-hop needle".

[22] In a mixed review, Seth Wilson of Slant Magazine took note of the album's "ingratiating charm" but criticized its lyrical content.

[24] Robert Christgau awarded the album an A− grade in his online subscription letter praising in particular Hunt's "way with words" prevailing throughout the record, citing the chorus of 'Body Like a Back Road' as an example of his words cherishing "the American vernacular that imbues great pop songwriting from Irving Berlin to Jay-Z in a Nashville dialect that recalls John Prine".