This Past Weekend w/ Theo Von

Podbit · This Past Weekend w/ Theo Von

#662 - Matt Rife

Explore episode Jun 10, 2026
Arts
Ralphie May Was Matt Rife's First Mentor

#662 - Matt Rife · Jun 10, 2026 Arts

At 16, Matt Rife cold-tweeted Ralphie May asking to open for him at a Cleveland club, and Ralphie said yes — until Rife's anxious mother flooded him with logistical questions and Ralphie had to cancel. Six months later he made good on it. Ralphie later took Rife to diners in LA and made him order three entrees so he'd have groceries for the week.

Where this was said

Young Matt Rife's Nashville Roots & Opening for Ralphie May

At 34:12 · chapter starts 30:18

Matt Rife traces his Nashville roots back to age 16, when he was already opening for established acts at Zanies. The most memorable story is his cold Twitter DM to Ralphie May at 16, which immediately resulted in a 'yes' — until his mother, unfamiliar with the comedy industry, bombarded Ralphie with questions about parking, tickets, and logistics. Ralphie politely withdrew, and Matt held a gentle grudge against his mom. Six months later Ralphie made good on it with a Youngstown theater show that paid $100 — and where Matt randomly met Tony Hinchcliffe's mother in the audience.

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