Rosie O’Donnell recently shared candid insights into her experiences with guests on her iconic talk show, revealing both her favorites and those who proved to be unexpectedly challenging. Appearing on the Australian talk show Sam Pang Tonight on October 13, O’Donnell, 62, highlighted a surprising name on her list of difficult interviews: Keanu Reeves.

While naming Barbra Streisand as her ultimate favorite and Martin Short as the best overall guest, O’Donnell recounted Reeves’ 1997 appearance on The Rosie O’Donnell Show. Despite her admiration for him, calling him “sweet” and “gorgeous,” she noted that Reeves was not adept at talk show dialogue. “He would not answer a question,” O’Donnell explained, detailing how attempts to engage him with simple questions like “So, Keanu, how’s it going? How are you feeling?” were met with monosyllabic responses like “Good.” Given the live nature of the show, O’Donnell eventually had to prompt Reeves directly, stating, “You know, Keanu, it is a talk show. You have to talk.” She clarified that Reeves eventually “got the hang of it” during subsequent appearances, emphasizing that he is a “lovely man and a good-hearted guy” and she didn’t want to unfairly criticize him.

However, O’Donnell couldn't resist referencing another particularly notorious interview: her fiery 1999 exchange with Tom Selleck. This controversial interview occurred shortly after the tragic Columbine High School shooting. Selleck had appeared in a full-page NRA advertisement proclaiming, “I am the NRA. Shooting teaches children good values.” Deeply affected by the Columbine tragedy, O’Donnell recalled feeling “torn up” and relentlessly questioned Selleck about his stance and perceived responsibility for gun deaths. The intense discussion garnered significant media attention, with Selleck famously accusing O’Donnell of “questioning my humanity” during the heated debate.