Historically, a paucity of comparative morphological characters has led to much debate regarding relationships within and among the major lineages of New World nine-primaried oscines. More recently, DNA-DNA hybridization studies have provided novel and testable hypotheses of relationships, although no consensus has been reached. For 40 songbird taxa, we obtained 1,929 base pairs (bp) of DNA sequence from the mitochondrial cytochrome-b (894 bp) and NADH dehydrogenase subunit 2 (1,035 bp) genes. Phylogenetic analyses confirm the monophyly of this assemblage as traditionally defined. The lineages delineated historically on morphological grounds are retained; finches (Fringillinae) are sister to a well-supported clade (Emberizinae) containing blackbirds (Icterini), sparrows (Emberizini), wood-warblers (Parulini), tanagers (Thraupini), and cardinal-grosbeaks (Cardinalini). However, each tribe individually is either paraphyletic or polyphyletic with respect to most recent songbird classifications. Our results suggest that Euphonia is not a tanager but perhaps represents a derived form of cardueline finch. Piranga, traditionally considered a typical tanager, is a cardinaline in all of our analyses. Calcarius falls outside the sparrow lineage in all of our analyses, but its true affinities remain unclear. Elements of four different AOU families are represented in our clade Thraupini. The inclusion of several “tanager-finches” (Haplospiza, Diglossa, Tiaris, Volatinia, Sporophila) and a nectarivore (Coereba) in this clade is consistent with findings from other molecular phylogenies in suggesting that convergence in feeding specializations among some lineages has confounded traditional morphological classifications. We obtained a novel arrangement of relationships among tribes in our “best” topology; Cardinalini is sister to the rest of the Emberizinae assemblage (as defined by Sibley and Ahlquist [1990]), and Thraupini is sister to a clade containing Icterini, Emberizini, and Parulini. Despite nearly 2,000 bp of sequence for each taxon, and a high degree of stability across most weighting schemes and analytical methods, most nodes lack strong bootstrap support. The ND2 gene provided higher resolution than did cytochrome b, but combining genes provided the most highly supported and resolved topology. We consider the phylogeny a working hypothesis to be used as a guide for further studies within the nine-primaried oscine assemblage.