The 2025 US Open Tennis Championships - Day 10: Owen Wilson and Ben Stiller are seen on Day 10 of the 2025 US Open Tennis Championships at USTA Billie Jean King National Tennis Center

NEW YORK, The 2025 US Open Tennis Championships Day 10 - SEPTEMBER 2, 2025 

Owen Wilson, Ben Stiller and Daymond John are seen on Day 10 of the 2025 US Open Tennis Championships at USTA Billie Jean King National Tennis Center on September 2, 2025 in Flushing Meadows, Queens, New York City. 

Photo: GettyImages 

Daymond John sits behind Owen Wilson and Ben Stiller

Owen Wilson and Ben Stiller are seen on Day 10 of the 2025 US Open Tennis Championships at USTA Billie Jean King National Tennis Center on September 2, 2025 in Flushing Meadows, Queens, New York City. Photo: GettyImages

Ben Stiller during the Men's Singles Semifinal match between Carlos Alcaraz of Spain and Daniil Medvedev of Russia

NEW YORK, NEW YORK - SEPTEMBER 08, 2023

Ben Stiller, Scott Galloway and Kara Swisher during the Men's Singles Semifinal match between Carlos Alcaraz of Spain and Daniil Medvedev of Russia on Day 12 of the 2023 US Open at the USTA Billie Jean King National Tennis Center in the Flushing neighborhood of the Queens borough of New York City. 

 

Scott Galloway, Ben Stiller and Kara Swisher

Scott Galloway and Ben Stiller

Ben Stiller as Derek Zoolander

Photos from GettyImages