We report four photocatalytically active cobaloxime complexes for light-driven hydrogen evolution. The cobaloxime catalysts are sensitized by different meso-pyridyl boron dipyrromethene (BODIPY) chromophores, bearing either two bromo- or iodo-substituents on the BODIPY core. The pyridine linker between the BODIPY and cobaloxime is further modified by a methyl substituent on the pyridine, influencing the stability and electronic properties of the cobaloxime catalyst and thus the photocatalytic efficiency of each system. Four cobaloxime catalyst complexes and three novel BODIPY chromophores are synthesized and characterized by absorption, fluorescence, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and electrochemistry. Crystal structures for the BODIPY-cobaloxime complexes 2 and 3 are presented. In contrast to the photocatalytically inactive, nonhalogenated reference complex 1, the four newly reported molecules are active for photocatalytic hydrogen evolution, with a maximum turnover number (TON) of 30.9 mol equiv of H2 per catalyst for the meso-methylpyridyl 2,6-diiodo BODIPY-sensitized cobaloxime complex 5. We conclude that accessing the photoexcited triplet state of the BODIPY chromophore by introducing heavy atoms (i.e., bromine or iodine) is necessary for efficient electron transfer in this system, enabling catalytic hydrogen generation. In addition, relatively electron-donating pyridyl linkers improve the stability of the complex, increasing the overall TON for hydrogen production.