This brief report describes methodology and results of a novel, efficient, and low-cost recruitment tool to engage high-risk MSM in online research. We developed an incentivization protocol using iTunes song-gifting to encourage participation of high-risk MSM in an Internet-based survey of HIV status, childhood sexual abuse, and adult behavior and functioning. Our recruitment methodology yielded 489 participants in 4.5 months at a total incentive cost of $1.43USD per participant. The sample comprised a critically high-risk group of MSM, including 71.0 % who reported recent condomless anal intercourse. We offer a “how-to” guide to aid future investigators in using iTunes song-gifting incentives.