Brad Pitt, George Clooney, and Angelina Jolie

George Clooney at an event for Up in the Air (2009)

George Clooney and Elisabetta Canalis at an event for Up in the Air (2009)

George Clooney, Brad Grey, and Sumner Redstone at an event for Up in the Air (2009)

George Clooney, Brad Grey, Jason Reitman, and Sumner Redstone at an event for Up in the Air (2009)

Brad Pitt and George Clooney in Wolfs (2024)

Brad Pitt, George Clooney, and Austin Abrams in Wolfs (2024)

George Clooney and Al Pacino in Ocean's Thirteen (2007)

Brad Pitt and George Clooney in Ocean's Eleven (2001)

George Clooney and Scott Jacoby in Return to Horror High (1987)

George Clooney in Return to Horror High (1987)

George Clooney and Lori Lethin in Return to Horror High (1987)

George Clooney and Michelle Pfeiffer in One Fine Day (1996)

George Clooney, Michelle Pfeiffer, Alex D. Linz, and Mae Whitman in One Fine Day (1996)

George Clooney and Quentin Tarantino in From Dusk Till Dawn (1996)

Brad Pitt, George Clooney, Matt Damon, Andy Garcia, Casey Affleck, Elliott Gould, Scott Caan, Bernie Mac, Carl Reiner, Eddie Jemison, and Shaobo Qin in Ocean's Eleven (2001)

George Clooney, Arnold Schwarzenegger, Alicia Silverstone, Uma Thurman, and Chris O'Donnell in Batman & Robin (1997)

Brad Pitt, George Clooney, Julia Roberts, Don Cheadle, Matt Damon, Andy Garcia, Catherine Zeta-Jones, Bernie Mac, and Jeffrey Wright in Ocean's Twelve (2004)

George Clooney and Diane Louise Salinger in Unbecoming Age (1992)

Brad Pitt, George Clooney, Don Cheadle, Matt Damon, Andy Garcia, Casey Affleck, Elliott Gould, Scott Caan, Bernie Mac, Carl Reiner, Eddie Jemison, and Shaobo Qin in Ocean's Thirteen (2007)