Rosie O’Donnell Dishes on Her Most Challenging Talk Show Guest

Comedian Rosie O’Donnell took to the Sam Pang Tonight Show to reflect on the legacy of her talk show, ‘The Rosie O’Donnell Show,’ which ran from 1996 to 2002. During the interview, she shared her perspective on some of the most memorable guest interactions, particularly highlighting Keanu Reeves as her most difficult interview.

O’Donnell recounted her initial encounter with the ‘John Wick’ actor during a 1997 episode, describing his minimal responses as a challenge. She noted, ‘He’s so sweet, he looks gorgeous, I love all his movies, but he would not answer a question.’ Despite the actor’s quiet demeanor, O’Donnell took on the role of encouraging him to engage, emphasizing the need for conversation in a talk show setting.

Praising Reeves’ character as ‘a lovely man and a good-hearted guy,’ O’Donnell admitted that he eventually adapted to the format after returning to her show in 2001. She praised both Martin Short and Barbra Streisand as her favorite guests, describing Short’s unique ability to make every interview a performance, with Short responding to O’Donnell’s greeting of, ‘How you doing, Marty?’ with the confident, ‘I’m here!’ O’Donnell’s talk show, which ended when she chose to focus on family, was later followed by ‘The Rosie Show’ on the Oprah Winfrey Network. The latter, however, was short-lived, canceled in 2012 due to low viewership.