David Letterman and Billie Eilish in My Next Guest Needs No Introduction with David Letterman (2018)

David Letterman and Suzanne Ciani in The David Letterman Show (1980)

Robert Downey Jr. and David Letterman in My Next Guest Needs No Introduction with David Letterman (2018)

David Letterman in The Comedy Store (2020)

David Letterman, The Kid Mero, and Desus Nice in PJ Boys (2020)

David Letterman and Dick Cavett in Late Night with David Letterman (1982)

David Letterman and Howard Smith in Late Night with David Letterman (1982)

David Letterman and Melinda Gates in My Next Guest Needs No Introduction with David Letterman (2018)

David Letterman and Tiffany Haddish in My Next Guest Needs No Introduction with David Letterman (2018)

Ellen DeGeneres and David Letterman in My Next Guest Needs No Introduction with David Letterman (2018)

Jim Carrey, David Letterman, and Jerry Lawler in Man on the Moon (1999)

David Letterman, Natalie Merchant, Steven Gustafson, Robert Buck, 10,000 Maniacs, and Morgan Fichter in Late Night with David Letterman (1982)

David Letterman and Norm MacDonald in Norm Macdonald Live (2013)

David Letterman, Norm MacDonald, and Adam Eget in Norm Macdonald Has a Show (2018)

David Letterman and Jay-Z in My Next Guest Needs No Introduction with David Letterman (2018)

George Clooney and David Letterman in My Next Guest Needs No Introduction with David Letterman (2018)

David Letterman and Garry Shandling in The Larry Sanders Show (1992)

David Letterman and Conan O'Brien in Conan (2010)

David Letterman and Chris Elliott in Cabin Boy (1994)

Steve Martin and David Letterman in Steve! (Martin): A Documentary in 2 Pieces (2024)

Emilio Estevez and David Letterman in Brats (2024)

David Letterman and Charles Barkley in Charles Barkley (2024)

David Letterman, Charles Barkley, Shaquille O'Neal, Ernie Johnson, and Kenny Smith in Charles Barkley (2024)

David Letterman and Ernie Johnson in Charles Barkley (2024)

David Letterman in Charles Barkley (2024)

Julia Louis-Dreyfus and David Letterman in Julia Louis-Dreyfus (2022)

David Letterman and Billie Eilish in Billie Eilish (2022)

David Letterman and John Mulaney in John Mulaney (2024)

David Letterman, John Mulaney, and Charles Mulaney in John Mulaney (2024)

David Letterman in My Next Guest Needs No Introduction with David Letterman (2018)

David Letterman in Late Show with David Letterman (1993)