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The funniest talk show hosts of all time
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The funniest talk show hosts of all time

In 2021, there are no shortages of talk shows hosted by some of the funniest people on Earth. So with that in mind, let's look at the 20 funniest talk show hosts of all time — and one who was the absolute worst.

 
1 of 21

David Letterman

David Letterman
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Letterman didn't invent the late-night talk show, but he may have come the closest to elevating to art. He took a sardonic approach to the trappings of the talk show itself, unimpressed by celebrity and often ending up openly hostile to his guests. Letterman's sketches were often brilliantly stupid, particularly Stupid Pet Tricks, various POV camera bits, from tiger to monkey, to any of Chris Elliott's bizarre characters. He made the theater crew and his own mother part of the show, turned Rupert Jee's Hello Deli into a tourist destination and influenced the subsequent generation of late-night hosts even more than Johnny Carson. You can see Letterman's influence on Jimmy Kimmel's show in particular, but you can even see it in how often things are presented in a list of 10.

 
2 of 21

Johnny Carson

Johnny Carson
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Here's Johnny! Still the king of late-night television, Johnny Carson manned the desk of "The Tonight Show" for 30 years, alongside announcer Ed McMahon. Carson had recurring characters like the clairvoyant punster Carnac the Magnificent and old lady Aunt Blabby, but he really shone with his monologues and improvising in weird moments, like when he got a lesson in throwing a tomahawk. And he was a tough interviewer — Robert Blake called it "facing the death squad," and that's Robert Blake saying that — with Carson only laughing when genuinely amused, unlike some of the subsequent "Tonight Show" hosts.

 
3 of 21

Jon Stewart

Jon Stewart
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Under original host Craig Kilborn, "The Daily Show" was a goofy, lighthearted parody of newsmagazine shows. Once Jon Stewart took over as the host, it turned into a nightly dismantling of all news shows and politicians of all stripes. It wasn't even restricted to his own show: Stewart's appearance on "Crossfire" was such a takedown that CNN cancelled the show weeks later. Stewart became a political figure in his own right, more Edward R. Murrow than Johnny Carson. In addition to regularly producing the smartest comedy show on television, Stewart was a generous straight man, which is how the show launched careers for Steve Carell, Stephen Colbert, John Oliver, Samantha Bee, Rob Corddry, Hasan Minhaj and more. Stewart also had some great, if short-lived talk shows prior to "The Daily Show," and the fictional version of Stewart nearly took over Larry Sanders' talk show.

 
4 of 21

Conan O'Brien

Conan O'Brien
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At his best, Conan O'Brien is a great sketch comedian who happens to host a late-night show. The strength of the show has always been in the bizarre sketches, devices and characters: The lever that played clips from "Walker, Texas Ranger" when it was pulled, Pimpbot 5000, countless two- and three-man scenes with Andy Richter and bandleader Max Weinberg. Over the years, Conan's monologues steadily improved, and he no longer needed sidekicks for support, especially when he's playing 1864 baseball.

 
5 of 21

Stephen Colbert

Stephen Colbert
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While Stephen Colbert's hosting job on "The Late Show" on CBS has been successful, he's never been better than he was hosting "The Colbert Report" on Comedy Central. Colbert did the whole show in character as a pompous conservative pundit, coining phrases like "truthiness" and bringing a nightly "Threatdown" of forces endangering America that was always bear-heavy. But somehow, the character remained endearing, in part due to Colbert's unpredictable in-character interviews, in which he would engage in what he called "ignorant deconstruction" of his guests' arguments. He's still charming on CBS, but it's nice that he occasionally brings out the old character, billed as his "identical twin cousin, Stephen Colbert" for legal reasons.

 
6 of 21

Ellen DeGeneres

Ellen DeGeneres
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Ellen was another superstar stand-up comedian who transitioned into talk show hosting. Her first show featured Ellen dancing at the end of her monologue, and it quickly became so iconic that within a year, American Express had her dancing through a commercial . Ellen combines the giveaways of Oprah with the goofy celebrity games of Jimmy Fallon and shows enough prank videos to rival Jimmy Kimmel. Lest you forget she's a comedian, Ellen recently put out her first stand-up special in 15 years.

 
7 of 21

Steve Allen

Steve Allen
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Steve Allen was not only the first host of "Tonight" on NBC, he essentially invented the format. Allen's show had an opening monologue, a house band, celebrity interviews and remote comedy bits, and in the opening of the first show, he announced that "This program is going to go on forever." Allen was talking about the run time of the show, but we're now in the 66th year of "The Tonight Show," which is longer than forever in TV terms.

 
8 of 21

Jimmy Kimmel

Jimmy Kimmel
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Jimmy Kimmel's first year at the helm of his own show was volatile, perhaps because the show was serving unlimited alcohol to its guests in the green room. But once the show settled down, Kimmel turned his focus to skewering pop culture, elaborate musical numbers about Matt Damon and getting parents to film themselves lying to their children. Still, despite the show's extreme pop culture focus, Kimmel's scathing wit comes through, like when he roasted Jay Leno on Leno's own show. And recently he's become a voice of moral conscience, which no one would have predicted in his "Man Show" days, talking about his son's heart surgery and the mass shooting in his hometown of Las Vegas. In this era of Woke Kimmel, the girls on trampolines from "The Man Show" would all be unionized and have a generous health care package.

 
9 of 21

Joan Rivers

Joan Rivers
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Can we talk? Joan Rivers certainly did, spending years as a guest host for mentor Johnny Carson on "The Tonight Show," before being banned from the show for a ridiculous 28 years for having the audacity to get her own show. Her late-night show didn't last, but her daytime talk show was a huge success, winning an Emmy and showcasing Rivers' quick-witted personality. She also had a syndicated daytime show as early as 1968, and in a less sexist era, she would have been even more of a television mainstay than she already was.

 
10 of 21

Dennis Miller

Dennis Miller
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"The Dennis Miller Show," Miller's first attempt at a late-night show, was derailed by booking wars with other late-night shows and lasted only seven months. However, the follow-up, "Dennis Miller Live," ran for eight years and won five Emmys. The HBO show stripped away a lot of the talk show artifices and focused on Miller himself: There was no house band, a sparse dark stage, an audience you never saw and just one guest. Instead, it played to Miller's strengths — jokes, more jokes and rants, despite his repeated protests that he didn't want to get off on one.

 
11 of 21

Rosie O'Donnell

Rosie O'Donnell
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After finding success as a stand-up comedienne and a movie star, Rosie O'Donnell got her own daytime talk show in 1996. It won five Emmys for Outstanding Daytime Talk Show in its six years on the air and contributed more to sales of Koosh balls than any show in TV history, as O'Donnell constantly shot them into the crowds during the show. The main hallmarks of the show were relentless positivity and over-the-top enthusiasm, as shown in her overwhelming passion for Tom Cruise and Barbra Streisand. O'Donnell was known as the "Queen of Nice" during her run, essentially the opposite of Jerry Springer in daytime TV, but she wasn't afraid to grill Tom Selleck about gun control either. And she was definitely your mom's favorite 20 years ago!

 
12 of 21

John Oliver

John Oliver
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John Oliver took over the reins of "The Daily Show" for a summer when Jon Stewart temporarily left to direct a movie, and he immediately proved he was too good to go back to a correspondent role. By December of that year, he had his own show on HBO, "Last Week Tonight," which has passed up "The Daily Show" as the pre-eminent political show on television. It proves British people are smarter, because Oliver only has to do one show per week. The political content is funny and illuminating, but the most memorable "Last Week" pieces are the elaborate projects — fake ads featuring the Catheter Cowboy that run on the Fox News affiliate in D.C. to reach the president, sending Russell Crowe's jockstrap to Alaska's lone Blockbuster Video and creating tobacco mascot "Jeff the Diseased Lung In A Cowboy Hat."

 
13 of 21

Seth Meyers

Seth Meyers
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Seth Meyers graduated from the Weekend Update desk and the head writer position at "Saturday Night Live" to take over a talk show on the same floor of 30 Rock. His time on Update feels like the foundation for Meyers' show, which eschewed the traditional standing monologue in favor of a seated monologue and desk piece where Meyers tells jokes with the help of over-the-shoulder graphics. The longer "A Closer Look" pieces have become the show's signature — and they're perfect for an era when people might not stay up to see them live at 12:35 a.m., but they'll definitely watch a five-minute YouTube clip the next day.

 
14 of 21

Arsenio Hall

Arsenio Hall
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One of those things that make you go hmmm is that Arsenio Hall's show only lasted five years. Despite being the first late-night show aimed at a young, urban audience, Hall's show was a big hit out of the gates, but fell victim to factors out of its control: namely, all the CBS affiliates who carried the show dropped it when David Letterman's show started, and ratings plunged. Still, Hall will always be known for his enthusiastic "Dog Pound" section of the crowd, the diversity of his guests and that time when Bill Clinton played "Heartbreak Hotel" during the 1992 presidential campaign. Hall's response was, "It's nice to see a Democrat blow something besides the election."

 
15 of 21

Craig Ferguson

Craig Ferguson
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When Craig Ferguson took over "The Late Late Show" in 2005, he initially kept the standard talk show format of scripted monologues and prepared celebrity interviews. But quickly Ferguson decided that the improvised ad-libs he was delivering did better than the stuff on cue cards, and he started improvising the whole thing, often tearing up his notes before talking to a guest. He also brazenly pre-taped portions of the show and didn't bother to pretend otherwise. Eventually the show also acquired a stable of puppets, a robot sidekick and a fake house band that was too shy to appear on camera. But Ferguson also had some genuinely touching moments, such as the times he eulogized his parents on air and one entire Peabody-winning episode devoted to Archbishop Desmond Tutu.

 
16 of 21

Dıck Cavett

Dıck Cavett
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Dıck Cavett was one of the few performers to create a genuine competitor to Johnny Carson with "The Dıck Cavett Show" in the early '70s. (There were various programs on various networks called "The Dıck Cavett Show" for nearly three decades.) Cavett's trademarks were his highbrow approach to comedy — he'd book authors, politicians, and rock musicians who were too edgy for Carson, and his very first guest was futurist Buckminster Fuller. It was an unpredictable array of guests: Salvador Dali once brought an anteater on stage with him, and a drunk Norman Mailer feuded with (and headbutted!) Gore Vidal on one episode. 

 
17 of 21

Jimmy Fallon

Jimmy Fallon
Theo Wargo/Getty Images for NBC

Jimmy Fallon may not be a hard-hitting interviewer, or even a soft-hitting interlocutor, but his edition of "The Tonight Show" realizes that the celebrity interview itself is played out. So Fallon has guests play giant beer pong or spin a "Wheel of Impressions." Plus, Fallon has legitimate musical chops and the good taste to hire The Roots as his house band, which allows for classic bits like Slow Jam the News. There's nothing wrong with Fallon's goofy, lighthearted approach to late night, even though his idea of political comedy is playfully tousling the future president's hair.

 
18 of 21

Garry Shandling

Garry Shandling
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As Larry Sanders, Garry Shandling played the greatest fictional talk show host of all time. But Shandling was also a great real-life talk show host, serving as Johnny Carson's main guest host for "The Tonight Show" in the '80s. In fact, Shandling turned down lucrative offers from both NBC and CBS to take over a late-night show after David Letterman's departure to CBS, choosing to keep making his sitcom about a late-night host instead.  

 
Zach Galifianakis
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Zach Galifianakis currently hosts "Between Two Ferns," the most awkward anti-talk show of all time, and certainly the only one where a host asked President Obama, "Where are you planning on building the presidential library, in Hawaii or in your home country of Kenya?" But before that, he had "Late World With Zach," a talk show that ran for 36 episodes on VH1 in 2002. The show's monologue was done Zach-style, where the mostly beardless Galifianakis would play the piano and throw out non sequiturs. It didn't work exactly, which is why Galifianakis eventually tried doing the monologue for kindergarteners instead.

 
20 of 21

Jack Paar

Jack Paar
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Jack Paar was the second host of "The Tonight Show" on NBC, taking over the job six months after Steve Allen. Paar turned "Tonight" from a variety show to a talk show, with his emphasis on conversations with guests and witty banter. His very first show had songs, sketches, extended interviews and a chimp. In 1960, when NBC censors cut one of his "controversial" jokes (Paar pretended to confuse a water closet with a wayside chapel – scandalous!), Paar walked off mid-show. He came back a few weeks later, and his first words were, “As I was saying before I was interrupted.” Paar went to explain, “I believe my last words were that there must be a better way of making a living than this. Well, I've looked...and there isn't."

 
21 of 21

Worst: Chevy Chase

Worst: Chevy Chase
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Chevy Chase is good at a lot of things: physical comedy, reading fake news on Weekend Update, slap fighting, the list goes on. But that list does not include hosting a late-night talk show, as evidenced by the five awkward, sweaty weeks of "The Chevy Chase Show" in 1993. Here's the disastrous first show of that run, where a visibly anxious Chase made the crowd sing "Happy Birthday" to Goldie Hawn's son, before Chase dropped his birthday cake on the ground in front of him. Then he begged the crowd to stand up and dance as Goldie tried to console Oliver Hudson.

Sean Keane is a comedian residing in Los Angeles. He has written for "Another Period," "Billy On The Street," NBC, Comedy Central, E!, and Seeso. You can see him doing fake news every weekday on @TheEverythingReport and read his tweets at @seankeane. In 2014, the SF Bay Guardian named him the best comedian in San Francisco, then immediately went out of business.

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