The late-night host woos Winfrey back to his show for the first time in nearly two decades

By Todd Peterson
Updated November 22, 2005 08:00 AM

When Oprah Winfrey last sat down for an interview with David Letterman, there was a different President Bush in the White House.

That was 16 years ago, before Letterman moved his show to CBS in 1993, and before a quiet and somewhat mystifying feud developed between the sardonic late-night host and the queen of daytime TV.

Now, Oprah is set to return to Letterman’s Late Show Dec. 1, on the same night the musical The Color Purple, which Winfrey is producing, opens on Broadway, the Associated Press reports.

Letterman made the announcement Monday during his taping.

“What a big night that is going to be – not only for us, not only for Oprah, but for Broadway. You have The Color Purple Broadway opening, and then right across the street here in this theater, you have Oprah appearing here. I mean, that’s what Broadway is all about – it’s a street of dreams,” Letterman said.

The source of the rift between the two isn’t exactly clear, although Winfrey has been on the receiving end of Letterman’s jokes for many years. When Letterman hosted the Oscars in 1995, he used her name for his failed “Uma, Oprah” joke. And in 2003, Letterman publicly lobbied to get Winfrey to appear on his show.

That same year, Oprah told Time magazine that she was “completely uncomfortable” appearing on the show as a target for Letterman’s cracks, but she turned the tables on Dave and asked him to appear on her show. Letterman turned her down.

“Here’s what would happen: I would go on the Oprah show, and I would break down and sob like a little girl I don’t want to have that happen,” he said.