McDermott started performing in Chicago coffeehouses in the early 1990s,[citation needed] incorporating elements of Irish music into an American folk rock sound.

"[3] In 2013, McDermott formed The Westies with Heather Horton, Ian Fitchuk, Joe Pisapia and Lex Price.

Performers on the record include Price, guitarist Will Kimbrough, keyboardist John Deaderick and McDermott's wife, Heather Horton on backing vocals.

It received critical acclaim from journalists such as John Apice, who wrote in Americana Highways: "McDermott isn't a song & dance man.

He's about as important, pertinent & reinforcing as James Taylor, Cat Stevens (Yusef Islam), Peter Himmelman, & John Hiatt.

There's a Tin Pan Alley quality, with intense songwriter delicacy that isn't mainstream pop music.

On the subject, the New Jersey Stage wrote, "McDermott is now part of a lofty winner's circle as the Tenco Award has previously gone to luminaries in the singer-songwriter pantheon such as Leonard Cohen, Joni Mitchell, Tom Waits, Sting, Jackson Browne, Elvis Costello, Randy Newman, and David Crosby.

A few international past winners include Caetano Veloso, Jacques Brel, Joan Manuel Serrat, and Milton Nascimento.

"[7] McDermott has performed "God Bless America" and "The Star Spangled Banner" at arenas and stadiums across the United States.