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“On the Bus Mall” chronicles the the experiences of two male prostitutes eking out a living in Portland, Oregon, where the band hails from. In 2013, Stereogum named the song the best Decemberists song – and of the many vignettes featured on Picaresque, it is often regarded as one of the saddest or most emotional. Adding to the song’s authenticity is its description of areas or neighborhoods in Portland. For this and its touching story, Willamette Week (an area paper) listed it as one of the top 21 songs about Portland.