Interviewing Interviewers

Conan O’Brien, Jimmy Fallon, Sean Evans, The Tonight Show, and Hot Ones

I often think about what it must be like for a famous chef to eat at another restaurant. There must be an urge to be judgmental, but an eagerness to see another person’s take on their shared craft. For the host chef, the added pressure to cook well for this established guest could just as easily be an exciting opportunity to show their worth. I like to think that both chefs, as cook and eater, would be in it for a true love of food, whether in the pan or on the plate.

I suppose then, that the same could be said for lots of people in lots of professions. A teacher attending a class, an actor watching a play, a writer reading a book, a barber getting a haircut, or a tailor getting fitted, to name a few of the endless examples. People who are renowned in their own craft must sometimes partake in the work of a peer, and each person on each side of the transaction feels something for it. 

This is also true for one of the most profound professions of the last century: The interviewer.

Among the many stories, films, events, and programs that are made by the masters of their day, the common person often learns about them through an interview. That interview could have been in writing, heard via radio or podcast, or, probably most often for the last hundred years, televised. That televised interview could have been formally journalistic, casual, or comedic. I am speaking, of course, of the Great American Talk Show.

Morning, noon, or night, you probably have had a favorite host at some time of day and some point in your life. They become more than a TV personality, even more than a star: They become part of your life. When you turn on the screen, you welcome them into your home. When they have an important guest on their show, it’s like they become a guest in your home, too.

They’re your morning coffee, your lunch break buddy, or your easy laugh before bed. Many have risen and fallen, but this routine of host interviewing guest has sustained through the years. There are countless examples to be covered, but at the end of the day - better yet, the end of the night - only one show really matters: The Tonight Show.

Since 1954, The Tonight Show has been NBC’s premier late night television program. It defined the late night format with jokes about the day’s events, celebrity interviews, musical performances, comedic showcases, and more. Steve Allen and Jack Paar were the first hosts of The Tonight Show. Then, Johnny Carson’s thirty year reign solidified the Tonight Show as the cultural monolith it is today. Or, tonight. Last time I crack that joke, I promise.

I was not alive for Johnny Carson, so I was only ever able to experience him through other people’s stories or old clips of his show. I cannot tell you much about him, so I encourage you to do a little bit of your own research to fully appreciate what he meant to the generations of fans he entertained, and the future stars he inspired.

There is a six part documentary called The Story of Late Night, which thoroughly covers the history of late night television. Episode two is all about Johnny Carson, and a lot of what I might refer to can be found across the whole documentary. Here’s all six episodes for your viewing pleasure: Episode 1, Episode 2, Episode 3, Episode 4, Episode 5, and Episode 6.

Appreciating Johnny Carson’s importance is the only way to fully appreciate the things that happened after he retired.

When Carson retired, many people believed that his natural successor should be David Letterman. Letterman hosted his own show, Late Night, which aired after Carson’s Tonight Show, so it seemingly made sense to push him forward a time slot, especially since he was already fantastically popular.

But NBC said no. So, Letterman left NBC to start The Late Show over on CBS (see episode 4 of The Story of Late Night). In an unprecedented move, NBC selected someone completely unknown to take over Late Night after Letterman.

Conan O’Brien.

Conan O’Brien was a comedy writer who had worked on Saturday Night Live and The Simpsons. He had never hosted a talk show, had barely appeared on television, but SNL’s Lorne Michaels saw something in Conan, and vouched for him (episode 4 of The Story of Late Night talks more about this). They gave him a shot, and after a fantastic premier and then a rough few years, Conan became a cultural icon to a new generation. He was silly and smart, he was edgy and grounded. For 16 years, the 12:35 time slot was his domain to reign.

Conan moved the medium forward, and he moved comedy forward. He did it in his own way. Eventually, it came time for Conan to take on The Tonight Show, moving up a time slot the same way Letterman wanted to.

And he did… Briefly.

Since Conan O’Brien is one of my favorite funny people and famous figures of all time, it only makes sense that his Tonight Show departure is one of the most compelling pop culture stories to me. I have repeatedly read articles, watched videos, and sought out new information on the events that led to Conan O’Brien leaving The Tonight Show. This has been extensively documented, and I don’t need to drive that history into the ground, so I again encourage you to do a little bit of research on what happened there, like watching the video linked here or watching episode 5 of The Story of Late Night.

In short: Conan deserved better.

Conan’s departure from The Tonight Show took his own career down a different path than he dreamed of. In doing that, it opened the door a few years later for Late Night’s new host to also have a chance to host The Tonight Show. This host would go on to receive more network support, and continues to host The Tonight Show to this day. Or, to this night, I should say. Sorry, broke my promise.

This host is Jimmy Fallon.

Jimmy Fallon was no unknown. He was a star on the same show Conan wrote for, and NBC’s other iconic late night television program: Saturday Night Live. He also starred in several movies, and was well-known and beloved by audiences already. Plus, he already had some hosting experience via SNL’s Weekend Update.

Fans of late night television have mixed opinions about Jimmy Fallon and the direction he has taken The Tonight Show. Where Conan’s style was defined by the fact that he was a comedy writer before a host, Jimmy’s style is defined by the fact that he was an actor/performer before he was a host. Conan put comedy above all else, Jimmy puts the show itself above all else.

Let me explain.

Conan was given a shot because he had goofy ideas and made other writers laugh when they worked together. This translated to him wanting to pursue those goofy ideas in sketches or remote segments. He would do whatever it took to get a laugh, be it reacting to someone else’s absurdity or becoming the absurdity himself. Conan once described his comedy as a Venn diagram between smart and stupid.

Jimmy is just as much of a comedian as Conan, but because his background was in stand-up comedy, sketch comedy, and big picture acting, he understood a key difference between being funny and being entertaining. That said, instead of trying to come up with the whackiest idea or the funniest bit, he wants to put on a show. Yes, Jimmy Fallon is hilarious, and has been a part of many hilarious works, but his show is more about the show itself than it is about pure comedy.

Jimmy’s Tonight Show has less sketches and more games with guests. When he tells you a story, he wants you to feel like you were there, and like you were in on how cool it was, more than he cares about a set-up and a punchline. He wants you to be entertained. Though it is ultimately a comedy show, Jimmy’s Tonight Show cares less that you laughed and more that you smiled.

Whether or not they were your favorite, both Conan and Jimmy are positively viewed and popular across wide audiences. They do, however, draw their criticisms, as anyone does. If you are not a fan of goofy comedy, you will not be a big fan of Conan. If you want your late night host to be more comedic and less viral, you will not be a big fan of Jimmy.

I used to be quite caught up in the criticisms of one late night host versus another, and I would take it oddly personally. However, a recent conversation reminded me of Teddy Roosevelt’s Man in the Arena speech.

In this speech, Roosevelt explains that anything worth attempting, whether you fail or succeed, is going to come with criticism. Conan has critics. Jimmy has critics. But those critics, who comment from outside of the arena instead of ever getting into the dirty battle of it themselves, are the “cold and timid souls who neither know victory nor defeat.” Though unrelated to this topic, you should read Teddy Roosevelt’s full Man in the Arena speech here.

Conan and Jimmy have several differences, in both their style as a host and the way in which they got there. There are also many things that bond both their histories and their humors. One thing that they certainly have in common, as do any talk show host, is that they are both masters in the art of interviewing.

You have to know your guest and your audience. You have to have some idea of their answers before you ask the question, while still allowing the freedom to fly away with it. It is a blend of structure and spontaneity, a balance of planning and improv. There are moments you step back and listen, and moments you speak up and guide the conversation. At the end of the day, it is all about making sure the audience has a good experience with your guest. How you get there is up to the host.

Critics spoke, years passed, and both Conan and Jimmy thrived in their own way. Eventually, fate would allow Conan to return to The Tonight Show as Jimmy’s guest. An experienced late night host being interviewed by another experienced late night host. A chef eating at another restaurant.

Only this time, the chef is returning to their old restaurant. Conan was not just being interviewed by another interviewer, but it was a successor to The Tonight Show. You can watch most of the interview here.

These days, I never stay up to watch any late night show. I just watch some of the videos the next day on YouTube, sometimes. When I found out Conan was going back to The Tonight Show, I set a reminder in my phone so I could stay up and watch it live. I’m glad I didn’t miss the moment.

When Conan walked out, The Roots (the band on Jimmy’s show) played a modernized version of his iconic theme song that the Max Weinberg Seven (the band on Conan’s show) played for years. The interview was delayed by a standing ovation from the studio audience, which Jimmy joined in on. It was Conan who had to settle the audience, either due to his own discomfort of such praise, or because he is a show biz professional through and through. Likely both.

At one point, Conan takes a moment to look down and touch Jimmy’s desk, almost longingly. Perhaps Conan, retired from late night television, was missing some of the glory of the old gig. Perhaps he was dreaming of what could have been on his Tonight Show.

There was something so important of Conan being a guest back on this show. It shows you the kind of person he is, who wants to move on from grudges and let go of bad feelings. You could see it in his Tonight Show farewell statement, and you could see it in the simple fact that he came back. He came back to the show he had to walk away from. Not a lot of people would have done that.

Beyond the symbolism of The Tonight Show as an institution, there was a deeper significance of Conan being interviewed by not just a peer, but his successor and old friend. Maybe not his best friend, I couldn’t say, but the two worked in the same building for a long time with the same goal of entertaining audiences. It had to be The Tonight Show, and it had to be Jimmy.

As the interview commenced, something unique happened: The guest took control. Conan took control. This is in no way a cut of Jimmy “losing control” of his guest. No, Jimmy was in awe of someone who was not just a guest, not just a friend, but a comedy hero. Someone he looked up to for years. Jimmy wanted to let Conan shine on his monumental return to the show he briefly called home.

Jimmy letting Conan lead the way was probably the best choice he could have made as the host, as the interviewer. When you think of it this way, it’s as if “giving up control” was the ultimate power move on his own show. Especially when you consider Conan had nearly 30 years of such televised interviews under his belt. This interview was a masterful display of both interviewer and interviewee playing their roles to entertain an audience.

And seeing Conan on the other side of the desk, considering where his career has gone since The Tonight Show, was beautiful. He deserved it. When you look at the outstanding work he has done, you realize that so little of it would have been possible if not for his NBC departure.

What the Tonight Show does for most hosts is elevate their career to match the mantle of the greatest franchise in television history. For Conan, I believe that it would have done the opposite.

The criticisms against Fallon, which I myself used to express, are unfair. I see that now. The Tonight Show isn’t meant to be risky comedy, it’s meant to be light and fun for everyone. That’s why Letterman didn’t get it, and why Conan didn’t last. I love Letterman, and I love Conan, but for both of them to do what they had to do, it could not have been on The Tonight Show.

That’s why Jimmy Fallon’s Tonight Show simply works. It isn’t always groundbreaking, but it does not have to be. It’s fun. It makes you smile. Isn’t that enough?

Conan deserved better, and if he had the time to grow his show, perhaps his Tonight Show could have driven comedy forward. But that isn’t what The Tonight Show is. For Conan to drive comedy forward, he had to go on tour. He had to go to cable. He had to go to his podcast. He had to go to streaming. He had to go online.

In the online era, everything has changed. Well, not everything. The goal of any show that gets produced is to entertain people, so they will watch, and you can advertise. More viewers, more advertising dollars. That’s show biz, baby.

Now, however, you don’t need the executive approval of one of the few major networks, or one of the many cable channels, to make a famous show. You can record yourself right now, take a risk, and post it. Sometimes it fails, but sometimes it skyrockets. In this new era of entertainment, a new interviewer has risen as a successor to all the greats before him in a whole new way.

His name is Sean Evans. 

Sean Evans is the host of Hot Ones, the show with hot questions and even hotter wings. If you’re a fan of the show, you know that is how Sean opens up every episode. On this show, which I love, Sean and his guest eat ten chicken wings covered in increasingly spicier and spicier hot sauces. After each bite, Sean asks an increasingly deeper and deeper question.

The idea is that when guests are under the influence of extreme heat, they let their guard down and give you real, vulnerable moments on camera. This oftentimes extends to their answers to Sean’s well-researched questions.

Seriously, it is almost comical how many guests will be stunned at not only the research Sean has done on his guest’s early life and work, but how intuitively he will ask his question to dig down to a deeper insight. Not only does Sean get a fascinating story from his guest, but he gets them to discuss a belief or a discovery that they may have never been given the opportunity to talk about.

That last sentence is important to understanding not only why Sean Evans is an outstanding interviewer, but why the art of interviewing is so important: You are giving your guest an opportunity to talk about something they may have never had a chance to before. You are giving your guest an opportunity to speak to their audience in a whole new way, as themself, independent of what they do. When you add in ridiculous reactions to hot sauce, you have a recipe for one of the hottest shows in this new landscape of entertainment.

Hot Ones’ popularity is not only evident by the tens of millions of views their videos get, but by the influential guests that Sean sits down with. I could go on and on about Sean and his show, but I can’t (right now). Instead, I am going to keep my focus on two of Sean’s influential guests who are also influential hosts of their own shows.

Conan O’Brien and Jimmy Fallon.

Conan’s appearance on the show broke the internet. He brought along a friend who played the character of his doctor. He ridiculed each sauce for being not spicy enough, several times opening the bottles to take a sip while commenting that there was no spice. He said this, though you could see the pain in his eyes. He sang, he screamed, he performed, he “never felt so alive,” and he dropped an unexpectedly amazing thesis of the art and history of comedy. It was manic. It was amazing. It was Conan. I have no words to describe it that would do a better job than just watching it for yourself.

Jimmy’s appearance on the show was much different than his bubbly Tonight Show persona. He was calmer, he was more grounded, he was very casually quick witted without emphasizing the joke or laughing through it. His reactions were real and subdued, not playfully performed. He even poked fun at his tendency to break (laugh) during old performances at SNL. What Jimmy lacked in the spectacle that Conan’s Hot Ones appearance had, he more than made up for it by simply being nice.

I cannot tell you how refreshing it was to see Jimmy just be Jimmy, for Jimmy to be exactly who you want him to be. “Pound for pound” (go watch the episode), it was one of the better episodes of this great show, in my opinion.

Conan and Jimmy’s Hot Ones interviews each did a phenomenal job of showing you who they were. Conan did bits, he made silly sounds, and he went to extreme lengths at his own painful expense to get a laugh. Jimmy cracked jokes quietly and knew when to perfectly call back to moments from earlier. He paid attention to Sean and kept their interaction conversational and lighthearted.

Jimmy also called out the fact that he has used Hot Ones as a segment on The Tonight Show, giving Sean praise as both a host and an innovator to their craft. Though I spent the bulk of this article talking about Conan, Jimmy, and late night television, Sean is an amazing interviewer. Even though his show airs on the internet and can be viewed as late or early as the viewer chooses, his show is here and now.

Hot Ones has paved a unique way forward, and I believe Sean Evans has cemented himself in the conversation with Conan, Jimmy, or any of the late night hosts that came before them. I hope Sean does Hot Ones for a long, long time. But, if he ever decides to go, I wouldn’t be shocked to see him become a late night host one day. Part of me hopes to see it one day, while part of me of me hopes he keeps doing Hot Ones forever. Because what Hot Ones has proven is that, thanks to the internet, you don’t need a late night time slot to make it anymore… Though it helps.

Though I loved Conan’s Hot Ones episode, it was Jimmy’s appearance that inspired me to write this piece. It opened my eyes about who he is, what he does, and why he is the perfect host for The Tonight Show. As someone who always wished for Conan’s Tonight Show to have lasted longer, and wondered what it could have become, it could never have been that way. Conan had other work to do, and Jimmy was meant for The Tonight Show.

Whether it was Conan’s episode, or Jimmy’s episode, or any of the hundreds of guests Sean has had on, Hot Ones gives viewers one of the most unique shows in entertainment history. You see them in pain, you see them sweat, you see them let down their PR-guard that their managers have built up for years. I think that is why Hot Ones is so hot. It is one of the few instances in entertainment where you see a celebrity guest be truly unfiltered and vulnerable, be truly human. We like to see humans as humans, and not just celebrities.

After all, that is why interviewers matter.

It wouldn’t be Hot Ones if it were just about the spicy wings, but Sean’s ability and willingness to research the unheard past of his guests gets them on his side every time. They trust Sean through this experience because he cares deeply about the person sitting across from the table. If he didn’t care, he would ask them the same ten questions every other interviewer likes to ask.

I am personally grateful to Sean and the entire Hot Ones team for providing these glimpses of Conan and Jimmy as they have never been seen before. Hosts that countless guests have trusted, now vulnerable guests themselves.

True, Jimmy has had Sean perform Hot Ones segments on the Tonight Show with a variety of guests, but this most recent bout against the wings of death made me appreciate him more than any other time I’ve ever seen him, wings or not.

As for Conan’s episode… It was pure magic. Pure, stupid magic.

Conan, Jimmy, and Sean are all masters in the unsung craft of interviewing. The best interviewers of all time are often overlooked, because a good interview lets the guest be the leader, while the host simply guides the path. I hope that I was able to give these interviewers the attention they deserve. They deserve it because, across many years and many mediums, many formats and many audiences, these hosts have gone after the same simple, wholesome goal:

To keep you, and me, and viewers everywhere entertained.

To keep us smiling.