Crookston's family origins include Hungary, and his website reports that polkas and Eastern European food figured in his upbringing.

Crookston's first label album, Fall Down as the Rain, was selected by Performing Songwriter Magazine as one of 2004's top 12 self-produced independent recordings, and was featured on National Public Radio's All Songs Considered, The Midnight Special and Folkscene.

Emulating Woody Guthrie, he spent a year traveling in the Finger Lakes region of New York state, collecting stories to turn into songs.

In Spring 2008, Crookston and the other "Most Wanted" award winners (Anthony da Costa, Randall Williams and Lindsay Mac) were sent on a 23 concert promotional tour in the northeastern U.S., with venues including the Kennedy Center and Club Passim.

He collaborated with The National WW1 Museum and Memorial in Kansas City MO to write the song, "The Letters of Florence Hemphill" about a 19 year old nurse who served in France during WWI.