74: Sky Captain and the World of Tomorrow with Emma Stefansky

Every year on Podcast Like It’s the 2000s, Phil and Emily pick one Chaos Pick a movie that doesn’t quite fit into any miniseries, but demands to be talked about anyway. This year’s selection is Sky Captain and the World of Tomorrow, the ambitious 2004 pulp-sci-fi experiment that looked like the future of filmmaking… and then quietly disappeared. Joining the conversation is Emma Stefansky, here to passionately defend Kerry Conran’s retro-futurist spectacle starring Jude Law, Gwyneth Paltrow, and Angelina Jolie. The group digs into the film’s groundbreaking all-digital production, its sepia-toned visual language, and why it feels like a volume-stage movie years before volume stages became standard. They also explore how Sky Captain fits into a lineage of stylized adventure films like Dick Tracy and The Rocketeer, and why audiences often remember how the movie looked more than what actually happens in it. Along the way, they discuss Roger Ebert’s glowing four-star review, the film’s middling box office and critical afterlife, the risks of resurrecting actors digitally, and whether Sky Captain is a misunderstood cult object or simply a fascinating near-miss. It’s a conversation about ambition, technology, and the strange movies that briefly convince us we’re looking at the future right before the future changes again. Hosted on Acast. See acast.com/privacy for more information.

You can listen to 74: Sky Captain and the World of Tomorrow with Emma Stefansky online on Radio and Podcast. Open the player on this page to stream the available audio.

74: Sky Captain and the World of Tomorrow with Emma Stefansky is an episode from Podcast Like It's 1999 by Phillip Iscove.

This episode is 1:23:15 long.

This episode was published on Dec 26, 2025.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Podcast Like It's 1999 when more episodes are available from the podcast feed.