Songs of individual male Blue Grosbeaks (Passerina caerulea) typically begin with the same combination of elements, but the sequence and number of elements in the latter portion of songs vary. We examined the possible functions of within-song variation in Blue Grosbeaks at the Blue Grass Army Depot near Richmond, Kentucky, USA from 15 April to 31 July 2007. We examined singing rates and song characteristics of second-year (SY; n  =  6) and after-second-year (ASY; n  =  14) males, and conducted playback experiments (n  =  15) to identify the possible function of variation in song length. Male Blue Grosbeaks sang at highest rates prior to pairing, maintained relatively high singing rates during the post-pairing/pre-nesting and nest-building/egg-laying stages, and sang at lower rates during the incubation, nestling, and fledgling stages. These results suggest high singing rates are important in attracting mates and establishing territories, and lower singing rates may result from trade-offs associated with parental care. Males used longer songs during aggressive encounters with conspecifics and responded more aggressively to playback of longer songs. This suggests songs containing more elements signal increased aggression. Within-song variation may be an important way to vary song meaning for male Blue Grosbeaks, and perhaps other males in species with a single song type but repertoires of several different song elements.