This week, Tommy is joined by actor Milo Ventimiglia, whose career has spanned beloved television roles, heartfelt dramas, and unforgettable characters that continue to resonate with audiences. From being stopped on the street for Jack Pearson to reflecting on the lasting cultural impact of Gilmore Girls and its sharp, enduring writing, Milo looks back on the characters that shaped his career and the complicated legacy of playing a “toxic” love interest. He shares what he really thinks about Jess today, the advice he would give his younger self, and why he has never been afraid of rejection. This conversation also explores maintaining boundaries between work and home life and why separating emotion from career has been key to longevity.

Milo also opens up about stepping into I Can Only Imagine 2, taking vocal lessons and guitar training for the role, and how personal loss, including losing his home in the fires just before welcoming his first child, deepened his connection to the story’s themes of faith, resilience, and gratitude. He reflects on what having faith means to him, why relying solely on work for happiness can be dangerous, and what his relationship is like with fear. Milo also speaks candidly about letting life experiences shape creativity rather than the other way around.

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Executive Producers: iHeart Media and Elvis Duran Podcast Network

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