"[4] Ryan is known for his "hushed rasp, with words catching like vows destined to be broken – one of modern music's most potent whispers.

After attending Valley Forge High School, Matthew Ryan arrived on the music scene on September 23, 1997 with May Day, produced by David Ricketts (Sheryl Crow, Meredith Brooks) and released on A&M Records.

Allmusic concluded, "The native of Chester, PA (near Philadelphia) was 25 at the time, but this is such a mature, emotionally honest effort that one got the impression he'd done more living than usual during his 25 years.

Ryan's voice is rough and has a very lived-in quality that proves most appropriate on such tales of loss, disappointment, and hurt as "Watch Your Step," "Chrome," and "Lights of the Commodore Barry."

It was recorded at Kingsway Studio in New Orleans (with additional sessions in both Nashville and Oxnard, California) and was co-produced with Trina Shoemaker (known for her work with Sheryl Crow and Giant Sand).

[10] 2002 was a quiet period for Ryan, who eventually released two collections of Stereo-Pak demo recordings, Dissent from the Living Room and Hopeless to Hopeful.

From a Late Night Highrise was met with the strongest wave of critical support Ryan has received to date.

"[13] In the early winter of 2011 Ryan started writing for his next album after moving from Nashville, Tennessee to a town just outside Pittsburgh, Pennsylvania (the state where he was born!).