Two chiral copper(II) complexes [Cu(L)2Cl]Cl (1) and [Cu(L)2Br]Br (2) {L = N-[(pyridin-2-ylmethylene)imino]dehydroabietylamine} have been synthesized and fully characterized. The coordination geometry of the CuII ions in 1 and 2 can be described as an intermediate between square-pyramidal and trigonal-bipyramidal. DNA binding studies suggest that the complexes interact with salmon-sperm DNA through intercalation, and 2 exhibits a higher binding affinity. The new complexes were screened for their antibacterial and cytotoxic ability. They have similar cytotoxic activity and they represent the first rosin-derivative-based simple Schiff base complexes with strong anticancer potential.