As expected, he was funny, especially when he chronicled his one-time attempts to be invited on her program. To prove it, he showed clips from his own Late Show, in which Barbara Walters, Martha Stewart, Julia Roberts and Tom Cruise all separately told Letterman they had been on the air with Winfrey. Stewart even pointed out that Winfrey gives her an entire hour.
“Why didn’t you just pick up the phone?” Winfrey asked him.
As was not expected, “He’s a li’l bit nervous,” said Winfrey, 53, before Letterman, 60, entered the Madison Square Garden stage, where the 22nd-season premiere of her show took place. His hands planted firmly in his suit pockets, Letterman appeared tight-lipped, even when she gave him a big, warm hug.
Later, his eyeglasses fogged up. “I think that also may be you, Oprah,” he explained.
Letterman didn’t spend his entire appearance joking. He spoke warmly about being a father, to 4-year-old son Harry, and called being a parent “ideal for me,” despite his also saying, “It is the constant razor’s edge – do you make your point with patience or discipline?”
During the 30 minutes Letterman sat and talked with her, Winfrey told him that when he “graciously” had her on his show in 2005 and then walked her down the street to the opening of the Broadway musical she produced, The Color Purple, it was “one of the highlights of my career.” To prove it, she showed Letterman the photograph of their walking together that is framed in her office.
Letterman was still gracious. Pulling a piece of paper from his suit pocket, he announced the Top 10 Reasons I Love Oprah:
10. She smells great.
9. Without her, we would never have known that quack, Dr. Phil.
8. She helped me start my wildly popular “D” magazine.
7. We’re yoga buddies.
6. Oprah’s incredibly busy, yet she still finds time to ignore my calls.
5. She agreed to validate my parking.
4. Taught me how to launder money in the Cayman Islands.
3. Any time I’m in Chicago she lets me crash on her couch.
2. Oprah gave me my first post-surgery sponge bath.
1. She’s giving everybody in today’s audience a new house.