Comedians Theo Von and Matt Rife dedicated a portion of their latest conversation on This Past Weekend to honoring the late Ralphie May, sharing stories of his immense generosity. Von recalled May's unique ability to connect across cultural lines, noting that "he loved, like being accepted by Black folks and white folks."
Rife shared personal memories of how May jumpstarted his career back when he was still an unknown teenager living in Ohio, letting him open at Zanies right before Christmas and providing critical financial support. "When I was, like, still living in Ohio, he used to let me come down here and do his shows right before Christmas at Zanies, and he would, like, I mean, he would pay me probably, like, five, $600, which, and I'm in high school, so that's like a million dollars to me-" Rife remembered, highlighting May's reputation for helping young comics get on their feet.
The affection for May ran deep in Rife's personal life as well. Rife revealed that his late father figure, Steve, was also an incredibly passionate fan of the comedian, telling Von, "Oh, dude, he fucking loved Ralphie, too." While the comedy world still feels the void left by May's untimely passing, his legacy of quiet generosity and universal appeal continues to shape the next generation of headliners.