Being a celebrity guest on a talk show isn't always smooth sailing- remember Dakota Johnson's infamous on-air clapback to Ellen DeGeneres over a birthday party invite? Celebrity interviews are a risky - but crucial - element of any talk show, since an exclusive chat with an A-lister can draw huge ratings or generate endless social media debate over a testy exchange. Legendary former Tonight Show host Jay Leno once revealed to Men's Health that a key to success as a host was finding ways to relate to his guests. "One thing I do that other talk-show hosts don't do is meet with each guest in the green room before the show," Leno said in 2003. "I let them know that I've seen the movie they're hawking, heard the songs on their latest CD, or read the book they just wrote. I never pretend, because sincerity is very important when you're trying to make someone comfortable. Someone else's work or interests always give me something to discuss. I never think for a minute that anyone is interested in talking to me about me. I think it's an assumption everyone should make." Radio Andy Hosts Share Their Biggest OMG Moments While On-Air Keep scrolling as Rosie O'Donnell, Jimmy Fallon, Andy Cohen, Stephen Colbert and more hosts reveal some of their favorite - and least favorite - guests of all time. Martin Short - Best Amy Sussman/Getty Images Rosie O'Donnell - who hosted her own daytime talk show for six years - singled out comedy icon Martin Short as a guest she could always rely on to keep viewers on the edge of their seats. "You come out and say, 'How you doing, Marty?' and it's over for you," she joked on Sam Pang Tonight in October 2025. "He stands up and he goes, 'I'm here!' He was the funniest and the nicest guy, so I would say Marty Short was definitely one of the best." Keanu Reeves - Worst O'Donnell was less enthusiastic about interviewing The Matrix star Keanu Reeves, who she suggested was simply not comfortable in the talk show format. "One of the worst, who, I love the guy, but he's not good on talk shows: Keanu Reeves," she admitted. "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 are you feeling?' [He'd respond] 'Good.' We were live. We couldn't retape. I finally said after three minutes, 'You know, Keanu, it is a talk show. You have to talk." The former Rosie O'Donnell Show host praised Reeves as a "lovely man and a good-hearted guy" before crediting him with improving as a guest over time. "He did come back, and he got the hang of it," she said. Patti Lupone - Best Neilson Barnard/Getty Images The Broadway diva's appearances on Watch What Happens Live With Andy Cohen are always iconic - from her infamously calling Madonna a "movie killer" to airing out her many grievances with Andrew Lloyd Webber. "[Patti's] a great one, always a classic," Andy Cohen said in 2020. "She's at a point in her life where she just doesn't care, and that's a wonderful place to be." Amber Rose - Worst Cohen played one of Watch What Happens Live's signature segments, "Plead the Fifth," during a 2016 appearance on The Rachael Ray Show, and was asked about his least favorite guest. "I will say, Amber Rose came on and she didn't want to answer any of the questions I was asking," Cohen explained. "She was wearing sunglasses. She actually said on the air, 'Am I your worst guest ever?' And I told her, 'You are in the running right now!' ... I really liked her a lot and after the show we had a laugh about it." Conan O'Brien - Best Paul Morigi/Getty Images Howard Stern has interviewed many of the world's biggest stars - including Paul McCartney, Barbra Streisand and Madonna - throughout his legendary career but he singled out a 2015 interview with fellow talk show host Conan O'Brien as his best ever. "I went home after [our] interview and said, 'This is the first time in my life [where] I feel like I asked every question I needed to ask and I feel like I had one of the most sincere conversations," Stern recalled on his SiriusXM show in 2019. "It was so fulfilling. It was funny. It was brilliant in terms of what [O'Brien] was saying. ... It felt complete." Stern described O'Brien as "super funny, insightful and bright," then admitted: "After the interview, in all my delusion, I thought we were going to become really good friends! ... He's the brother I would want." Gilda Radner - Worst The original Saturday Night Live cast member was beloved for her charming personality, though her witty nature didn't necessarily translate into a great interview for Stern. The two crossed paths during Stern's early years at WNBC in New York City - and it's safe to say they didn't hit it off. "There are some people who just won't give you anything," Stern told Larry King Live in 2006. "And I'm thinking back all the way like 20 years ago when I was on NBC. Gilda Radner was really freaked out by me." Stern suspected that may have come into the interview with preconceived concerns