Eric D’Alessandro on Italians, Boomers, AI, Streamers, Comedy (S5E23)

from Will Love Listen · host Will Love Listen

Eric D’Alessandro joins the pod to poke fun at Italians, boomers, streamers, and AI. Eric discusses parenting today, why younger generations are not aging like older generations, and how the fuck were Tony Soprano and George Costanza in their 30s during The Sopranos and Seinfeld? Eric also breaks down why serious comics and streamers have caused the line between performance vs real life to be blurred. If you say something is a joke, but you actually believe it, is it really comedy!?

Episode metadata supplied by the publisher feed · Published Jun 16, 2026

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Eric D’Alessandro on Italians, Boomers, AI, Streamers, Comedy (S5E23)

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