In 1999, television host David Letterman bought a 2,700-acre ranch in Montana. According to Realtor, the ranch is one of several properties owned by Letterman, who has spoken openly about moving away from the pressures and lifestyle associated with show business.Letterman, now 79, was born and raised in Indianapolis. He left Indiana in 1975, when he was in his late 20s, to pursue a career in stand-up comedy. He later became one of American television’s best-known late-night hosts, spending much of his career in New York before stepping away from his long-running show in 2015.After his decision to leave late-night television, Letterman and wife, Regina Lasko, moved back to Indiana, where he said he felt more comfortable being himself. He has described his years in show business as a period when he felt he had been pretending to be someone he was not.
Life away from show business
In a 2024 interview with GQ, Letterman spoke about the difference between his life in show business and his life in Indiana. He said returning to his home state had helped him reconnect with a broader part of life outside television.“In show business, I find that I have pretended to be someone I’m truly not. In my life here in Indiana and at my home with my family, I am probably the person I actually am. And I regret that they don’t kind of cross at any point,” Letterman said.When he was asked whether he believed Hollywood had made him a “worse person”, Letterman agreed. “Yes. You’re exactly right,” he said.Letterman also said that his priorities had changed after leaving his late-night show. “I just feel like, personally, I have greater humanity than I did when I was in show business. It was all single-minded and great pressure, real unimagined, and I felt like it’s all on me and it’s all on me, and that it was all nonsense,” he said.Letterman had hosted his popular late-night programme for 22 years before leaving in 2015. Even after stepping away from the show, however, he did not completely leave television behind. He continued working on screen while also spending more time away from the demands of late-night television.
Letterman’s properties
The Montana ranch became one of Letterman’s major properties during this period. He bought the 2,700-acre ranch in 1999.
Letterman grew up in a modest three-bedroom house in Indianapolis.
The ranch is not his only large property outside Indiana. Letterman also owns a compound in upstate New York made up of two separate properties purchased more than a decade apart.His first New York purchase was an 88-acre estate in North Salem. The property has a large main residence and a swimming pool. In 2007, he bought an adjoining 20-acre plot for around $5 million.
The childhood home
Letterman’s connection to Indiana goes back to his childhood. He grew up in a modest three-bedroom house in Indianapolis. The home recently changed hands for $347,500.The property is now being rented through Airbnb for $200 per night. Its connection to Letterman is a major part of its appeal, with the listing describing it as his childhood home in Broad Ripple, a neighbourhood in Indianapolis.The listing highlights the house’s location near restaurants and shops and describes it as a quiet property in a tree-lined neighbourhood. It also mentions updated bathrooms, comfortable beds and a screened porch.Letterman himself does not live in the childhood home. Instead, after returning to Indiana, he bought another property for himself and his family.His return to Indiana has been part of a wider change in how he views his life. He has said that during his years in television, his attention was focused almost entirely on his programme and the demands that came with it.“All I cared about was television, one hour of television that I was responsible for, for 30 years. That’s all I cared about,” he said. “Everything fell apart, went away. I didn’t even know if it was falling apart or not. And now I have the energy and the broader focus to recognize humanity has other fulfilling pursuits.”
Connection to Indiana remained
Although Letterman spent many years away from Indiana, he continued to maintain a connection with the state. He is a part-owner of Rahal Letterman Lanigan Racing and has remained closely associated with the Indianapolis 500.In a 2019 interview with NBC, he also spoke about how much Indianapolis had changed while he was living in Los Angeles. He said he often depended on familiar landmarks to find his way around his hometown.“Every time I come here, I get lost. I don’t recognize things, I know landmarks, and I can find my way to the speedway,” he said. “I know where Broad Ripple High School is. I know where Monument Circle is. I know where Long’s Doughnuts is off 16th Street. I know where Shapiro’s Deli is and a few landmarks like that.”
