
The Bill Simmons Podcast Ben Stiller on 'Tropic Thunder,' Comedy in 2019, the Knicks, and His Biggest Career Lessons, Plus Bill's Dad | The Bill Simmons Podcast
Mar 22, 2019
Ben Stiller, the acclaimed actor and director, shares insights into his career, from 'Tropic Thunder' to 'Escape at Dannemora.' He discusses the challenges of pursuing comedy in today's world, the nostalgic impact of films like 'Reality Bites,' and the cultural evolution of filmmaking. Stiller reflects on his experiences with the Knicks, showcasing the emotional highs and lows of being a fan. Bill Simmons also calls his dad, leading to a lively conversation about basketball playoffs and the Celtics' aspirations.
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Word-of-Mouth and Theatrical Experience
- "There's Something About Mary's" success is attributed to positive word-of-mouth and a strong theatrical experience.
- This organic growth, now rare due to quick streaming releases, created a communal viewing experience.
De Niro and Meet the Parents
- Stiller recalls being surprised by Robert De Niro's interest in working with him on "Meet the Parents".
- This marked a turning point in Stiller's career, realizing his comedic clout.
Celebrity Encounters
- Stiller shares anecdotes of encountering celebrities he parodied, like Tom Cruise and Bruce Springsteen.
- He emphasizes that his impressions were never malicious, often arising from project needs.


