The Stand-Up, the Struggle, and Sobriety: Comedian Jeffrey Jay Gets Real

What happens when you’re a rising stand-up comic, a trans man in Texas, and a high-functioning alcoholic all before your 21st birthday? In this unforgettable episode of Drunk-ish, host Stefanie Wilder-Taylor sits down with the hilarious and brutally honest Jeffrey Jay, a groundbreaking transgender comedian who built a career making people laugh—while privately battling a deepening addiction to alcohol.

Jeffrey opens up about his early start in comedy, his unconventional (and deeply loving) upbringing with a Republican judge for a mom, and the ingenious hustle he pulled off in high school to keep himself stocked with booze. He talks candidly about the toxic drinking culture in stand-up, what finally drove him to rehab, and how he found healing, purpose, and self-respect on the other side of addiction.