Background: We explored predictors of cigar product initiation among Hip Hop-identifying U.S. youth using data from the U.S. Food and Drug Administration’s Fresh Empire evaluation. Participants were Hip Hop-identifying youth living in evaluation markets who had not initiated cigar product use at their first survey. Objectives: We modeled cigar product initiation odds using discrete time survival analysis logistic regression models as a function of factors related to one’s large social, physical, social/normative, and intrapersonal environment, and other tobacco use. Results: In the unique sample, 26.2% initiated cigar product use. Factors associated with higher cigar product initiation odds included: current/former (vs. non-susceptible never) cigarette smoking (odds ratio [OR]=5.35; p=.008); cigarette experimentation (vs. non-susceptible never smoking) (OR=3.26; p<.001); current (vs. never) e-cigarette use (OR=2.06; p<.001) and hookah use (OR=1.83; p=.011); having at least one friend who uses marijuana (OR=1.43; p=.008); high music use (OR=1.32; p=.035); household tobacco use (OR=1.26; p =.042); increased age (OR=1.18; p< .001); and higher sensation seeking (OR=1.16; p=.018). Youth reporting higher perceived smoking risks had lower cigar product initiation odds (OR=0.86; p=.029) as did Hispanic (OR=0.53; p<.001) and non-Hispanic Other youth (OR= 0.68; p=.023) (vs. non-Hispanic Black youth). Conclusions: The finding that high music use predicted cigar product initiation should be considered in light of cigar brand sponsorship of musical artists and events and indicates a potential opportunity for counter messaging. Peer crowd segmentation in this study identified unique and differing factors that influence tobacco use risk among Hip Hop-identifying youth that are not found in the general population.