The band mixes genres such as rock, funk, jazz, jive, blues, surf, R&B, reggae, rockabilly, rap, and psychedelic. Their sound has also been described as "equal parts Screamin’ Jay Hawkins, bizarre electronica, creepy hip hop and in-your-face gonzo rock". Gypsy jazz has been used in description of the band, while Godforbid himself describes the band's music as "fringe pop".

The band was founded in Boston by Godforbid and Jeremy Page, both members of the hip hop group Alaskan Fishermen.

In late 2004, That Handsome Devil, sometimes abbreviated "THD," released their first single, "Dating Tips" featuring three songs, "Dating Tips", "How to Get Money", and "Don't Go", which received mostly mediocre scores from magazines and other reviewers. July 23, 2006, saw the release of their first eponymous EP That Handsome Devil, which included the single "Dating Tips" from 2004. "Elephant Bones", the fourth track on the album, was featured as a bonus song in Guitar Hero II.

Their first studio album, A City Dressed in Dynamite, was released on August 5, 2008 to scores of positive reviews, being praised as "profoundly entertaining", "bizarre in a beautiful way" and "a madcap musical frenzy as dizzying as it is dazzling". Although the music continued to be as stylistically varied as their last release, the album expanded on the band's prevalent themes of emptiness, drug addiction, materialism, and death, and continued to feature their trademark of dated soundbites from the 1950s.

A portion of "Mexico" was featured in the seventh episode of season four of Weeds, "Yes I Can", before A City Dressed in Dynamite was released, though they are mistakenly credited as The Handsome Devils (Another band called The Handsome Devils had produced a song titled "Mexico" though this is a coincidence). "Squares" was later heard in the episode "Rebellion" of Reaper.

"Rob the Prez-O-Dent" was featured as the fourth track on Good Riddance, George W. Bush, released in December 2008, a compilation album of anti-George W. Bush songs, even though, despite its premise, "Rob the Prez-O-Dent" doesn't refer to George W. Bush or his policies at all; though "Viva Discordia" contains overt references to the Iraq War and the Bush administration, referring to the latter as "a bunch of mobsters looking for Osama".

"Rob the Prez-O-Dent" was also featured as a playable track in Rock Band 2. This, along with the appearance of "Elephant Bones" in Guitar Hero II, has greatly increased their visibility.

Their next EP, Enlightenment's For Suckers was released on August 25, 2009.

THD is planning a national tour for Summer, 2010.

That Handsome Devil EP (2006) Stardust/Traffic