Rosie O'Donnell Names Surprising A-Lister as Her "Worst" Talk Show Guest

Talk show legend Rosie O'donnell just spilled some serious tea during a trip to Australia, revealing which beloved Hollywood star gave her one of her toughest interviews ever. And trust us, you probably won't see this one coming!

TL;DR

• Rosie O'Donnell called Keanu Reeves one of her "worst" talk show guests during a 1997 interview.
• She clarified that she "loves the guy" but he "would not answer a question" during the live segment.
• O'Donnell praised Martin Short and Barbra Streisand as her favorite and best guests, respectively.

Rosie's Shocking Revelation on an Australian Late Night Show

Rosie O'Donnell, the iconic host of The Rosie O'Donnell Show which graced our screens for almost 1,200 episodes between 1996 and 2002, is currently down under in Australia. She's there with her one-woman show, "Common Knowledge," and while promoting it, she made a guest appearance on the Australian talk show Sam Pang Tonight. And let's just say, she didn't hold back!

During her chat with Sam Pang, the conversation naturally turned to her illustrious talk show career and the myriad of celebrities she's interviewed. When asked about her best and worst guests, Rosie dropped a bombshell that has since gone global. Prepare yourselves, internet:

The Unexpected "Worst" Guest: Keanu Reeves' Memorable Visit in 1997

According to O'Donnell, one of her most challenging interviews came from none other than the "Internet's Boyfriend," Keanu Reeves. Yes, the same Keanu known for his "good-guy-ness and humility" (as one article put it)!

Rosie recounted the 1997 interview, which took place when Reeves, then 33, was promoting his movie The Devil's Advocate. Her main issue wasn't with his personality, but his conversational skills (or lack thereof) on live television.

"I love the guy, but he's not good on talk shows," O'Donnell candidly stated. "He's so sweet. He looks gorgeous. I love all his movies, but he would not answer a question. I'd say, 'So, Keanu, how's it going? How you feeling?' [He'd say] 'Good.'"

Imagine being a talk show host live on air, needing to fill minutes of time, and getting one-word answers from a major star! Rosie admitted it got to a point where she had to gently, but firmly, prod him. "We were live, we couldn't re-tape. I finally said after like three minutes, 'You know Keanu, it is a talk show, you have to talk!'" she recalled. She even offered him a snack or a toy to try and get him to open up more.

Keanu's Own Struggles with Talk Shows Revealed Publicly

It turns out that Keanu's reticence wasn't a personal slight against Rosie, but a genuine discomfort with the talk show format itself. During that same 1997 appearance, after Rosie's gentle nudge, Reeves confessed on air, "I'm not comfortable with them, but they're fun. It's alright." This honest admission sheds light on why someone so beloved and seemingly approachable might struggle in that particular setting.

His natural introversion, often noted by fans and colleagues, seems to have been particularly amplified under the pressure of live TV. For a host like Rosie, who thrives on quick wit and engaging banter, a quiet guest can be a real challenge to navigate, especially when there's no opportunity for retakes.

From Awkward to "Getting the Hang of It": Reeves' Eventual Return to the Show

Despite the initial awkwardness, it wasn't the last Rosie saw of Keanu on her set. She was quick to clarify that there's no bad blood and that he actually improved with subsequent appearances.

"But he did come back, and he got the hang of it," O'Donnell added. She reiterated her affection for the actor, stating, "But he's a lovely man and a good-hearted guy, so I don't wanna throw him under the bus." One article specifies he returned in 2001, showing his willingness to give it another shot.

This shows a mutual respect and understanding. Rosie, known for her warmth, clearly understood that his struggle wasn't intentional, and Keanu, in turn, worked on his interview skills. It's a testament to both their professionalism and the enduring appeal of "The Rosie O'Donnell Show" that guests were happy to return.

Spotlight on the Best: Martin Short and Barbra Streisand's Stellar Appearances

While Keanu may have been a challenging guest, Rosie also fondly remembered her favorites. She highlighted two A-listers who consistently delivered fantastic interviews.

• Martin Short: The "Best" Guest Rosie described Martin Short as "definitely one of the best." Why? Because his energy was infectious and immediate. "Because you come out and say, 'How you doing, Marty?' and it's over for you," she laughed. "He stands up and he goes, 'I'm here!' He was the funniest and the nicest guy." Short's comedic brilliance and willingness to perform made him a dream guest for any talk show host.
• Barbra Streisand: The "Favorite" Guest The legendary Barbra Streisand was "probably" O'Donnell's "favorite" guest of all time. While no specific anecdote was shared about Streisand's visit, her status as a cultural icon and multi-talented performer likely made her interviews a truly special occasion for Rosie, who often expressed admiration for her guests.

More Unforgettable Moments: Beyond Keanu with Tom Selleck and Elisabeth Hasselbeck

Rosie's career as a talk show host wasn't just about fun and games; she also had her share of heated and memorable exchanges. She touched upon a significant interview with Tom Selleck in 1999, shortly after the tragic Columbine massacre.

"It was very awkward. I had never been unkind or controversial, but Columbine had just happened," O'Donnell shared. She challenged Selleck, who had an NRA advertisement stating, "I am the NRA. Shooting teaches children good values." Rosie, deeply affected by the tragedy, pushed him on his stance on gun laws. "I was so torn up about Columbine that I just didn't give up," she admitted. The interview made headlines, with Selleck later commenting on O'Donnell's fiery style.

She also reflected on her very public on-air dispute with Elisabeth Hasselbeck on The View in 2007, over American military activity in the Middle East. The segment became so intense that the show's producers controversially cut to an unprecedented split-screen. O'Donnell recently alleged that this argument was a "setup" by the show's late producer, Bill Geddie, a claim Hasselbeck tearfully refuted on Instagram, urging Rosie to "stop the lying." These moments showcase Rosie's willingness to engage in serious topics, even when it led to conflict.

Keanu Reeves: Still the Internet's Boyfriend and What's Next for Him in Film

Despite his past talk show woes, Keanu Reeves, now 61, remains one of Hollywood's most beloved figures, affectionately known as the "Internet's Boyfriend." His career is as busy as ever, and fans are always eager to know what he's working on.

Currently, Reeves is hitting the promotional circuit for his new supernatural comedy film, Good Fortune. This exciting project, directed by Aziz Ansari, hit theaters on October 17, 2025. In the movie, Reeves takes on the role of an angel named Gabriel, starring alongside a fantastic cast that includes Seth Rogen, Sandra Oh, and Keke Palmer. He even recently appeared on Travis and Jason Kelce's "New Heights" podcast to chat about the film, showing he's still out there promoting, perhaps with improved talk show chops!

His upcoming slate continues to be packed, with future installments in his hugely popular franchises like John Wick and potentially more from The Matrix universe always a possibility. His genuine personality and dedication to his craft ensure he remains a fan favorite, whether he's a chatterbox on a talk show or a man of few words.

Rosie O'Donnell's Current Chapter: Comedy, Activism, and Life in Australia

Rosie O'Donnell, at 63, is not slowing down. Her one-woman show, "Common Knowledge," is bringing her unique brand of comedy and commentary to audiences in Australia. This trip also comes after a significant life change for Rosie, who relocated to Ireland in January 2025. She cited concerns over potential political changes in the U.S. and their impact on her non-binary 12-year-old as a primary reason for her move.

Her ongoing, well-documented feud with Donald Trump, which began in 2006, continues to surface, with Trump even threatening to revoke her citizenship in July 2025. O'Donnell has used her social media platforms, including Instagram, to respond to these threats, often referencing controversial figures to bait Trump. While these political discussions are a significant part of Rosie's public life, her current tour and recent revelations remind us of her lasting impact on the entertainment world and the candid insights she can offer from behind the scenes.

The Enduring Appeal of Talk Show Revelations and Celebrity Stories

Rosie O'Donnell's latest revelations serve as a fun reminder of why we love behind-the-scenes Hollywood gossip. It's always fascinating to hear what really goes down when the cameras are rolling and how even the most composed stars can have their awkward moments. It humanizes these larger-than-life figures, showing us that even Keanu Reeves, the epitome of cool, might just be a bit shy when it comes to small talk.

These stories give us a glimpse into the unique pressures of live television and the art of the interview, highlighting the dynamic between host and guest. And for fans, it's a delightful peek behind the curtain of the shows and stars we admire. So, whether it's a quiet Keanu or a boisterous Martin Short, every interview adds another layer to the rich tapestry of celebrity history!

FAQ: Your Burning Questions About Rosie, Keanu, and Talk Shows Answered

When did Keanu Reeves first appear on The Rosie O'Donnell Show?

Keanu Reeves first appeared on The Rosie O'Donnell Show in 1997. He was promoting his film The Devil's Advocate at the time.

Who were Rosie O'Donnell's favorite and best talk show guests?

Rosie O'Donnell named Martin Short as her "best" guest due to his engaging and energetic presence. She also called Barbra Streisand her "favorite" guest.

What is Keanu Reeves' new movie?

Keanu Reeves' new supernatural comedy film is called Good Fortune. It was released on October 17, 2025, directed by Aziz Ansari, and also stars Seth Rogen, Sandra Oh, and Keke Palmer.

How many episodes did The Rosie O'Donnell Show run for?

The Rosie O'Donnell Show ran for almost 1,200 episodes over six seasons, from 1996 to 2002.

Sources:

• Rosie O’Donnell Reveals Surprising A-List Star as ‘Worst Interview’
• Rosie O'Donnell Calls Keanu Reeves One Of Her 'Worst' Talk Show Guests
• Sam Pang's Rosie O'Donnell interview hits headlines worldwide after anti-Trumper's controversial Keanu Reeves confession
• Rosie O'Donnell Thinks Keanu Reeves Was One of the Worst Guests She Ever Had
• Keanu Reeves ‘Not Good’ on Talk Shows, Claims Veteran Comedian
• Rosie O'Donnell Reveals the Upsetting Choice For Worst Celebrity Guest on Her Talk Show