David Letterman holds a record that will likely never be passed. From 1982 until 2015, the comedian ruled late night television, hosting consistently for 33 years, first on NBC and then on CBS. Over that time, he amassed a fortune and established the successful Worldwide Pants production company.
Celebrity Net Worth estimates that Letterman has a net worth of $400 million and was earned $20 million a year from hosting The Late Show with David Letterman when he retired. Letterman also stayed on Forbes‘ Celebrity 100 list for 2015, earning an estimated $35 million that year. Now retired, the 69-year-old Letterman can enjoy life.
Here’s what Letterman has done with his money and how he has earned it.
1. Letterman’s Worldwide Pants Produced ‘Everybody Loves Raymond,’ so He Makes Thousands From Syndication
Worldwide Pants famously produced Everybody Loves Raymond, which ran from 1996 to 2005 and starred comedian Ray Romano. The show is still in syndication and, according to The Hollywood Reporter, runs in 150 countries. There have even been foreign-language remakes of the series. In 2005, TBS shelled out $650,000 per episode, notes AdAge.
Worldwide Pants also produced The Late Late Show with Craig Ferguson, but it doesn’t have much more in the making. According to IMDb, WWP only had one project on the slate at the time of Letterman’s retirement – a movie called The Revised Fundamentals of Caregiving with Paul Rudd and Selena Gomez. The movie opens in June.
2. Letterman Has a Warehouse Full of Ferraris
Owning one Ferrari might be enough for some, but not for Letterman. Like former rival Jay Leno, Letterman loves cars and reportedly has a warehouse in Danbury, Connecticut filled with 28 of them.
The Connecticut Post reported in 2012 that 10 of those cars are Ferraris. A 2011 list of the vehicles in Danbury showed that Letterman’s entire collection of cars is worth $1.2 million.
Letterman also co-owns Rehal Letterman Lanigan Racing with three-time IndyCar champion Bobby Rahal and Mi-Jack co-owner Mike Lanigan. He joined the team in 1996.
3. Letterman Faced a Salary Cut Before Retiring & Wasn’t the Highest-Paid Late Night Host
By the time Letterman retired, he was not the highest-paid late night talk show host. In 2013, TVGuide found that The Daily Show‘s Jon Stewart had passed Letterman and Leno, earning $25-30 million a year at that point from Comedy Central. Letterman and Leno both took pay cuts and were earning about $20 million. At that time, Leno was still hosting The Tonight Show.
The pay cuts for Letterman and Leno came as ratings for The Late Show and The Tonight Show among younger viewers was slipping. According to TheWrap, when Letterman began on CBS in 1992, he was averaging a 4.39 rating in the 18-49 demographic. By 2014, that had fallen to a 0.53 rating in that all-important demographic for advertisers.
4. Letterman Started a Foundation Called the Letterman Foundation for Courtesy & Grooming
For a comedian who enjoys growing out a beard, Letterman has a strangely-named independent foundation called The Letterman Foundation for Courtesy and Grooming. The foundation doesn’t have a website, but the Foundation Center reports that it awarded $540,253 in grants in 2013. The foundation was established in 1993.
Letterman’s foundation has supported Doctors Without Borders and the American Cancer Society, as well as Letterman’s alma mater, Ball State University. In fact, Letterman has been a major supporter of Ball State, donating much of his Late Show archive to the university after retirement. The university also named the David Letterman Communication and Media Building after him.
Ball State President Paul W. Ferguson said of the collection in a statement:
This collection will become part of The David Letterman Experience to be housed in the Letterman Building, extending a legacy of excellence, learning and preparation for our students into the 21st century.
5. Letterman Loves Big Sky Country & Lives on a Ranch
Although Letterman is an Indiana native, he lives part time in Whitefish, Montana, where he has a ranch. In an interview with the Whitefish Review, Letterman said he fell in love with the state. He said that Big Mountain is his favorite place to go skiing with his son, 12-year-old Harry. Letterman told the magazine:
The last time we were out there at Big Mountain—I guess they call it Whitefish Mountain now, you’re looking into the Canadian Rockies, then you’re looking back at Glacier, then you’re looking south to the ranges that run forever in that direction. One of my early ski instructors said to me that the first lesson in skiing is that when you get off the chairlift, take in the view. We’d been half way up the chairlift and it was like an IMAX movie. It’s beyond an IMAX movie—it’s all there. It’s crazy. You don’t see stuff like that.
Letterman does have plenty of other homes. He has homes on Martha’s Vineyard and Se. Barth’s. He also has a home in New Salem, New York that he bought in 1994 for $4 million, reports Zillow. The manison’s interior covers 8,000 square feet and has seven bathrooms.
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