The lyrics address topics that affected Hood around the time the songs were written, such as the birth of his child and his success with the Drive-By Truckers.

The album received mainly favorable reviews from critics, who praised it for being optimistic and mature in its handling of both positive and negative themes.

Some also commended it for addressing these themes in a compassionate manner, and for being exceptionally personal compared to his previous work with the Drive-By Truckers.

Half of the songs on the album were written when Hood moved to Athens in 1994, before the Drive-By Truckers were established,[2] and soon after his previous band, Adam's House Cat, disbanded.

[4] Stuart Henderson, writing in PopMatters, described its music as "grinding three-or-four chord garage rock, [and] drive-heavy reverb" and its lyrics as "throaty storytelling, a hefty dose of gallows humour, and a few slow-burning excursions into some poor schlub’s bleak night".

[5] "Murdering Oscar" tells a tale of a "morally elastic hitman" inspired by the Woody Allen film, Crimes and Misdemeanors (1989).

[10] "Walking Around Sense" displays a sound similar to that of Crazy Horse, and some have speculated that the song may be criticizing Courtney Love's parenting ability.

[18] Joshua Klein wrote that Hood was "surprisingly sanguine, even mature" in the way he addressed both positive and negative topics on the album,[10] and AllMusic's Mark Deming wrote that its songs were "dark but compassionate character studies", adding that it "consistently cuts closer to the bone" than Hood's first solo album, Killers and Stars (2004).

"[5] Henderson also argued that the music of Murdering Oscar discusses variations on the story of "the lonely, forgotten everyman", which he called one of Hood's favorite themes.

[19] It was ranked 316th on the Village Voice's 2009 Pazz & Jop,[20] 39th on Robert Christgau's 2009 "Dean's List",[21] and was named the fifth best album of 2009 by Steven Hyden of The A.V.