Talk Show Hosts Reveal Their Favorite — And Least Favorite — Guests

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.”

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

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

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

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 about his “insane” radio antics.

“She came in and she was very shaky and kept sort of getting up and she got up quick to leave and hit her head on a speaker,” he remembered. “And she was just, it was a disaster. And you never know, you just never know who’s going to be good.”

Bruce Springsteen — Best

Conan O’Brien shared a special connection with Bruce Springsteen since E Street Band drummer Max Weinberg worked on his late night show when he wasn’t touring with “The Boss.”

“Bruce Springsteen, we were fortunate enough to have on our show a couple of times,” O’Brien revealed on The Howard Stern Show in 2022. “He would show up early, he would rehearse. He knew all the cameramen’s names, he learned their names. He was a gentleman.”

O’Brien went on, “[Springsteen] crafted it. He figured it out. You think, ‘He doesn’t need to prove anything on Late Night With Conan O’Brien. He’s got nothing to prove! He’s got nothing to prove to anybody!’ Then, he’s hanging out afterwards and thanking people? You think, this is not an accident. There’s a reason he’s Bruce Springsteen.”

Abel Ferrara — Worst

As O’Brien wrapped up his 30 years in late night TV, he named a 1996 interview with the Bad Lieutenant director as a low point. He told the “Armchair Expert” podcast in 2018 that Abel Ferrara wasn’t simply unruly on-air, he allegedly tried to flee the studio too.

“He was this wild eccentric,” O’Brien told host Dax Shepard. “And he fled during the show before his segment. He ran away, got on the elevator and was out on the street running away and [producer] Frank Smiley gave chase. … He came on camera against his will, came out and started yelling at me.”

O’Brien admitted his interview with the filmmaker was a deeply unpleasant experience but it helped prepare him for tough interviews later in his career.

“It was like if you ate 15 cloves of garlic, you wouldn’t say that was a great experience but you’d remember it,” he joked.

Cardi B — Best

Tonight Show host Jimmy Fallon name-checked Barack and Michelle Obama, Cher and Bob Dylan as some of his most memorable guests, before revealing Cardi B’s 2017 appearance might be his all-time favorite.

“I was not prepared, nor were many people prepared for Cardi B,” Fallon admitted to The Hollywood Reporter in 2019. “That was one of those things where I’ve seen her in interviews and thought, ‘Wow! She’s really interesting and weird, so different.’ We’re two different people but I loved it!”

Fallon was so amazed by “the way [Cardi] talks” that he let her take the lead during an appearance on The Tonight Show.

“It exploded. That was Cardi-Mania,” he teased. “It was one of those things we didn’t even prepare for. We just thought it would be a fun interview but it just went crazy all over the place. … I love that! It was great.”

Robert De Niro — Worst

While Fallon has a reputation for being very supportive and friendly with his guests, he got off to a rough start with Robert De Niro as the first-ever guest on the premiere of his Tonight Show predecessor, Late Night With Jimmy Fallon, in 2009.

“In real life [De Niro] doesn’t even talk much,” Fallon quipped on Watch What Happens Live With Andy Cohen in 2011. “It’s not easy to get guests when you first come out, as a talk show … I wanted to get somebody A-list and I wanted to get somebody from New York because our show came from New York. The first person in my mind was Robert De Niro.”

Unfortunately, De Niro wasn’t the most cooperative guest when he sat down with Fallon for the latter’s NBC debut.

“He came on and he was Robert De Niro. Just one word answers. … Flop sweat is coming down my face and I go, ‘Oh my gosh,’” Fallon noted. “What I learned from that is to make the studio much cooler. We have an air conditioner so it’s icy cold in my studio!”

Will Smith— Best

Arsenio Hall looked back on his groundbreaking 1990s talk show during a 2013 interview with Parade, where he named Mariah Carey, Bill Clinton and former CBS News anchor Dan Rather as some of his favorite guests. However, Hall pointed to his 1991 interview with the Fresh Prince star as a particular highlight.

“[Will is] always funny, never stale,” Hall said. “He will always get you ratings, but reinvents himself for each appearance; he’s part of the family. We were to rap what CNN was to news.”

Vanilla Ice — Worst

The rapper’s 1991 appearance on The Arsenio Hall Show delivered one of the most cringeworthy TV interviews of all time. Arsenio Hall challenged Vanilla Ice on his street cred multiple times during a tense exchange.

“I’m not sure if I was poking fun at him because, to be totally honest with you, I wasn’t feeling funny,” Hall told VLAD TV in 2014. “I’d had a long, hard day and I probably wasn’t feeling like teasing anyone.”

Hall suggested he’d been “misled with some information” and fed “intentional lies” about Ice’s backstory, which fostered a hostile environment for their interview.

“I felt I was being used and my audience trusts me,” he declared. “My audience knows that if I say it, I believe it … It just was a confrontational day. I probably didn’t deal with Vanilla Ice in the way people are accustomed to me dealing with guests. I’m a ‘warm and fuzzy’ guy. It wasn’t a ‘warm and fuzzy’ day. I don’t think I was teasing him. I think I was pissed!”

John Oliver — Best

Stephen Colbert gave his former Daily Show coworker and Last Week Tonight host John Oliver a sash for being his “most frequent guest” in 2019.

Oliver made his record-setting 21st appearance on The Late Show With Stephen Colbert in September 2025 to kick off Colbert’s final season on CBS.

Donald Trump — Worst

Colbert and Donald Trump’s notorious feud has raged on for years, though many may not know that the future president actually visited The Late Show With Stephen Colbert once in 2015. During a 2020 appearance on Watch What Happens Live, Colbert explained why his showdown with Trump was forgettable.

“I wouldn’t want to [interview him] anymore,” Colbert said. “I did once and he was actually kind of disappointing. He played the ‘reasonable man.’ He’s always kind of in ‘persona mode.’ Sometimes he plays the ‘rallying populist’ and sometimes he plays ‘reasonable man.’”

The Late Show host likened Trump to “some guy you might meet at a [country] club” when he’s off camera, but then he “puts on a persona for the camera.”

“The persona he gave me when he was on [my show] was actually very quiet and very safe. He wouldn’t even make eye contact for most of it,” Colbert said. “He played it extremely safe and that’s always boring. He’s essentially boring.”