What do Stephen Colbert and an entire generation of Hollywood veterans have in common? They're both facing abrupt career disruption. Elaine Low, Sean McNulty and Natalie Jarvey explore the existential crisis facing Gen X, as careers stall out amid consolidation, AI and a Boomer blockade — and reveal what’s coming next for millennials. Then, Lesley Goldberg breaks down the shocking cancellation of The Late Show, revealed days after a $16 million Paramount settlement with President Trump. Was the ouster of late night’s highest-rated star really just a matter of money? And why didn’t his manager tell him about it for weeks? Plus: Sean checks in on summer box office, where The Fantastic Four is about to face the audience.

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