George Clooney and David Letterman in Late Show with David Letterman (1993)

David Letterman and Richard Simmons in Late Show with David Letterman (1993)

Clint Eastwood and David Letterman in Late Show with David Letterman (1993)

Bill Murray and David Letterman in Late Show with David Letterman (1993)

David Letterman and LeBron James in Late Show with David Letterman (1993)

David Letterman and John McCain in Late Show with David Letterman (1993)

David Letterman and Maria Sharapova in Late Show with David Letterman (1993)

Frank Fritz and Mike Wolfe at an event for Late Show with David Letterman (1993)

Gillian Anderson, Mary-Louise Parker, Simon Pegg, and Richard Simmons at an event for Late Show with David Letterman (1993)

Amanda Seyfried at an event for Late Show with David Letterman (1993)

Benedict Cumberbatch at an event for Late Show with David Letterman (1993)

Bob Dylan at an event for Late Show with David Letterman (1993)

David Letterman, Tom Malone, and Paul Shaffer at an event for Late Show with David Letterman (1993)

David Letterman at an event for Late Show with David Letterman (1993)

Dave Grohl and Foo Fighters at an event for Late Show with David Letterman (1993)

Felicia Michele Collins, Anton Fig, Will Lee, Tom Malone, Sid McGinnis, Paul Shaffer, Aaron Heick, and Frank Greene at an event for Late Show with David Letterman (1993)

David Letterman, Tom Malone, Paul Shaffer, Aaron Heick, and Frank Greene at an event for Late Show with David Letterman (1993)

Still of Tae Dye on the Late Show with David Letterman

David Letterman and Justin Bieber in Late Show with David Letterman (1993)

David Letterman and Joaquin Phoenix in Late Show with David Letterman (1993)

David Letterman in Late Show with David Letterman (1993)

David Letterman and Al Gore in Late Show with David Letterman (1993)

David Letterman and Nancy Pelosi in Late Show with David Letterman (1993)

David Letterman and Sacha Baron Cohen in Late Show with David Letterman (1993)

Beck in Late Show with David Letterman (1993)

Jorge Garcia in Late Show with David Letterman (1993)

Jerry Seinfeld and David Letterman in Late Show with David Letterman (1993)

David Letterman, Regis Philbin, Barbara Gaines, Biff Henderson, Alan Kalter, and Paul Shaffer in Late Show with David Letterman (1993)

Lindsay Lohan in Late Show with David Letterman (1993)