Variety praised McCrudden's film Islander for its “deeply felt performances” and “intimate, powerfully atmospheric” style.
[citation needed] His film Anita O'Day: The Life of a Jazz Singer (which he co-directed) won the Satellite Award for Best Documentary Film by the International Press Academy and was nominated for Best Long Form Music Video at the 52nd Annual Grammy Awards.
McCrudden has directed the films Child of Grace (Ted Levine, Maggie Elizabeth Jones), Cowboys & Indians (Ruby Knox), The Things We Carry (Alexis Rhee), Äntligen midsommar (Luke Perry, Lisa Werlinder, Olle Sarri), Islander (Phillip Baker Hall), the documentary Anita O' Day: The Life of a Jazz Singer, Trespassers (Michelle Borth), The Big Day (Julianna Margulies), Mr. Smith Gets a Hustler (Alex Feldman), and Trailer: The Movie.
He also directed one-woman show "Patriotic Bitch", written and performed by Alanna Ubach, in New York City.
McCrudden has contributed songs for many of his films and his debut album Start Over was released in March 2007, followed by Dream Anyway in 2010.