To better understand men's reluctance to seek help for mental health issues, we investigated the contributions of depression, stigma, and masculinity on help-seeking likelihood in a sample of depressed men. Two-hundred and fifty-eight men, who screened positive for depression on the PHQ-2, completed measures assessing self-stigma, self-reliance, emotional control, and general help-seeking likelihood via an online Qualtrics survey. Path analysis using MPlus tested one model of moderated mediation and two mediation models among the variables. Results supported a partial mediation model where (a) self-reliance, emotional control, and self-stigma directly related to lower likelihood of help-seeking, (b) self-reliance and emotional control predicted greater self-stigma, (c) depression predicted greater self-reliance and emotional control, (d) self-reliance and emotional control had indirect effects on help-seeking being partially mediated by self-stigma, and (e) depression had significant indirect effects on both help-seeking and stigma, being fully mediated by self-reliance and emotional control. We discuss the need to develop practices and interventions that address self-stigma's contribution to men's help-seeking through the complex relationships between depression and men's self-stigma as mediated by self-reliance and emotional control. Limitations to the study and future research directions are discussed.