Quote · The Bill Simmons Podcast
Spain Prevails, World Cup Winners and Losers, and Damon Vs. Leo With Chris Ryan and Anthony Dabbundo
Where this was said
Matt Damon vs. Leonardo DiCaprio
At 1:28:06 · chapter starts 1:09:00
The debate is framed by Chris Ryan's opening observation: DiCaprio has twice as few films as Damon and treats himself like a brand — only Leonardo DiCaprio parts with Leonardo DiCaprio directors. Damon, by contrast, will pop up in a Soderbergh garage shoot, do SNL, and take ensemble supporting roles. Bill walks through a dozen custom categories. Damon wins: iconic rewatchables (Rounders, Bourne, Ocean's Eleven, Interstellar), action films (the entire Bourne franchise), ensemble movies (Ocean's, Oppenheimer, Saving Private Ryan), comedy, range, TV work, screenwriting, and director buddies in sheer number (Soderbergh, Nolan, Lonergan, Kevin Smith). DiCaprio wins Oscar bait, most iconic single movie moments (the Titanic prow, the bear scene), younger films, and Best Picture batting average [1] — Bill Simmons "Bill Simmons built a full category-by-category case for why Matt Damon deserves to be in the conversation with DiCaprio. Damon wins action …" 1:08:24 . The Departed head-to-head is a draw: DiCaprio won the movie but Damon had the harder part. Both agree The Odyssey — Damon playing Odysseus in Christopher Nolan's technically groundbreaking epic — is the best Damon has ever been, and Chris Ryan concedes that after seeing it, he would rather have Damon's career than DiCaprio's.
Matt Damon has approximately 100 acting credits compared to Leonardo DiCaprio's 48 (including TV), illustrating Damon's willingness to say yes to a wide variety of projects.
Matt Damon turned down Avatar to film Bourne Identity. The deal would have given him 10% of box office, which would have been worth approximately $250 million.
Leonardo DiCaprio has cited not doing Boogie Nights as his biggest career regret, though skipping it also meant he was available to make Titanic.
Matt Damon's films have grossed an estimated $12 billion at the box office, nearly double Leonardo DiCaprio's $6.5 billion, though Damon has made roughly twice as many movies.
LeBron James' prolonged free agency deliberation is causing real problems for NBA scheduling, with commissioner Adam Silver flagging the issue publicly. Bill Simmons remains convinced Cleveland is the destination, despite prediction markets briefly spiking Miami to 55%.
