David Letterman and Regina Lasko welcomed their son Harry in November 2003 Stephanie Kaloi is a contributing writer at PEOPLE. She has been working at PEOPLE since 2022. She has also written about ...

“They tell me he’s in college,” said David Letterman when joking about his son, Harry, during an appearance on the Sept. 28 episode of Jimmy Kimmel Live! During this rare return to late ...

David Letterman said he didn't expect to be hit so hard emotionally after he dropped his 18-year-old son Harry off at college on Tuesday's episode of Jimmy Kimmel Live. The 75-year-old former ...

David Letterman came out of retirement last year ... Letterman opened up about his real passion in life, his son, Harry. When Willie asked the 72-year-old broadcasting legend if he misses his ...

When David Letterman's girlfriend Regina Lasko last ... be involved in something so beautiful as the creation of his son, Harry Joseph, became a first-time father at age 56, just a year shy ...

David Letterman is sharing his experience of recently ... "Jimmy Kimmel Live," during which he cracked a joke about his son Harry, 18, moving away to college. "Harry is my son, and all reports ...

Harry Letterman loves airplanes, bugs and leaving his toys in places he shouldn’t, his dad shared yesterday on the season premiere of Oprah. The 3 1/2-year-old son of David Letterman is not yet ...

“I always think of that and I pester Harry. ‘Have we had the talk? We should. Especially now. Let’s have the talk.’ ” His voice trails off and he laughs again. David Letterman knows ...

Precious little is known about David Letterman and the life he lives away from the Ed Sullivan Theater. He has a home upstate with his wife Regina Lasko and son Harry, 11, and he has a ranch in ...

David Letterman stood out in bright colors Wednesday while celebrating the New Year with his wife Regina Lasko and son Harry in St Barts. The 72-year-old comedian wore a white T-shirt with a small ...

“I could never imagine ever being a part of something that turned out this beautiful,” the proud dad said on his show after ...