He has been a member of major indie pop and punk bands, most notably Guided by Voices, Nada Surf, Bambi Kino, Death of Samantha, and Cobra Verde.

[3] Beginning in high school, Gillard began performing with Ohio punk bands such as Suspect Device, Children's Crusade, and Starvation Army.

[2] He has also performed and/or recorded with Richard Buckner, Yuji Oniki, My Dad Is Dead, The Mice, Bill Fox, Fence Lions, Zest of Yore, Stewart Pack, The Oranges Band, Mascott, and Sally Crewe and The Sudden Moves.

[2] Robert Pollard, who had been a fan of Gillard's since his Death of Samantha days, asked Cobra Verde in 1996 to be his backing band for Guided by Voices' Mag Earwhig!

"[2] Trouser Press called Hexed a "tuneful rush of smart, catchy and simple rhythm guitar pop-rock – sort of grown-up Weezer without the anxious pretensions.

"[10] According to Trouser Press, Gillard's contributions stood out as "crafty," with "the woolly and weird chant of 'Sheep,' the bracing T. Rex borrowings of 'Your Heroes Hate You' and the countryfied pun of 'Only a Loan.

[11] The band also includes Nada Surf drummer Ira Elliot, Mark Rozzo (guitarist for Maplewood and Champale) and Erik Paparazzi (bass player for Cat Power).

As a result, he’s able to synthesize disparate pieces that other people wouldn’t imagine fitting together until they saw the completed puzzle.... Doug deserves more attention, no doubt.

"[3] AllMusic's Mark Deming called Parade On an eclectic and superbly crafted album of "guitar-fueled rock & roll with an extra portion of pop hooks" and lyrics in "various degrees of bittersweet snark.

"[20] Deming praised Gillard as a gifted songwriter, guitarist, producer, and arranger, whose multi-instrumental performances included layers of strong lead and rhythm guitar work melding with "tough yet flexible" bass, in the service of songs ranging from "sparkly jangle" to "sweet but aggressive" hard-rocking power pop.

[24][25] In 2014, Gillard recorded a version of Scott Miller's song "Dripping with Looks," which originally appeared on the 1987 Game Theory album Lolita Nation.

[3] The song "Say Goodbye", with Gillard on guitar and lead vocals, and Peter Buck on mandolin, appears on the posthumous Game Theory album Supercalifragile (2017).