Winfrey and Letterman additionally appeared collectively in a Late Show promo aired throughout CBS's protection of Super Bowl XLI in February 2007, with the two sitting next to one another on a couch watching the sport. Three years later, during CBS's protection of Super Bowl XLIV between the Colts and the new Orleans Saints, the 2 appeared again in a Late Show promo, this time with Winfrey sitting on a sofa between Letterman and Leno. Letterman appeared as a visitor on CNN's Piers Morgan Tonight on May 29, 2012, when he was interviewed by Regis Philbin, the visitor host and Letterman's longtime good friend. Despite Johnny Carson's clear intention to pass his title to Letterman, NBC chosen Jay Leno to host The Tonight Show after Carson's departure. Three years after he left for CBS, HBO produced a made-for-television movie called The Late Shift, based mostly on a guide by The new York Times reporter Bill Carter, chronicling the battle between Letterman and Leno for the Tonight Show internet hosting spot. Letterman has said that he was initially unable to pinpoint the noise inside his head and free nude video that he hears a relentless ringing in his ears.

Letterman appeared in the pilot episode of the brief-lived 1986 sequence Coach Toast, and seems with a bag over his head as a visitor on Bonnie Hunt's 1990s sitcom The Building. Letterman has denied this. Letterman, Bobby Rahal, and Mike Lanigan co-own Rahal Letterman Lanigan Racing, an auto racing team competing within the WeatherTech SportsCar Championship and NTT IndyCar sequence. He also appeared as himself within the Howard Stern biographical movie Private Parts and the 1999 Andy Kaufman biopic Man on the Moon, in just a few episodes of Garry Shandling's 1990s Tv collection The Larry Sanders Show, and in "The Abstinence", a 1996 episode of the sitcom Seinfeld. In October 2022, Letterman traveled to Kyiv, Ukraine, to movie a particular standalone episode of My Next Guest Needs No Introduction with David Letterman, interviewing Ukrainian president Volodymyr Zelenskyy. Season four premiered on May 20, 2022, with Billie Eilish as the first visitor.

On February 1, 2022, Letterman was the visitor on Late Night with Seth Meyers, marking the 40th anniversary of the franchise's debut. Letterman started his production firm, Worldwide Pants Incorporated, which produced his show and a number of other others, in 1991. The corporate also produces function films and documentaries and founded its own file label, Clear Entertainment. He had a cameo in the characteristic movie Cabin Boy, with Chris Elliott, who labored as a author for Letterman. During the early years of the Late Show's run, Letterman often used a few of Carson's trademark bits, together with "Carnac the Magnificent" (with Paul Shaffer as Carnac), "Stump the Band", and the "Week in Review". The Letterman Foundation for Courtesy and Grooming is a private foundation by which Letterman has donated millions of dollars to charities and different nonprofit organizations in Indiana and Montana, superstar-affiliated organizations reminiscent of Paul Newman's Hole within the Wall Gang Camp, Ball State University, the American Cancer Society, the Salvation Army, and Médecins Sans Frontières.

The appearance was Letterman's idea: Leno flew to New York City on an NBC company jet, sneaking into the Ed Sullivan Theater in the course of the Late Show's February 4 taping carrying a disguise and meeting Winfrey and Letterman at a dwelling room set created in the theater's balcony, the place they taped their promo. Palin was in New York City at the time with Willow, and none of her different kids were at the sport. These included a statutory rape joke about Palin's then 14-yr-outdated daughter, Willow, and MLB player Alex Rodriguez. Some contemporaries questioned the racial connotations of joking a couple of Latino player of Dominican descent committing statutory rape. The possession of rape pornography is illegal in Scotland, England and Wales. In Week 13 of the 2021 NFL season, Letterman joined Peyton and Eli Manning on their Manningcast feed of the Monday Night Football sport between the new England Patriots and Buffalo Bills.