Starcast Join the waitlist
For Crying Out Loud

For Crying Out Loud

Introducing Drunk-ish: Jeffrey Jay

Oct 28, 2026 · 54m

Coming soon to iPhone. Already have it? “Listen in Starcast” takes you straight there.

About this episode

This episode was special to my for obvious reasons! 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…