The 32 Greatest Talk-Show Hosts Ever, Ranked

Photo: Illustration: Maya Robinson and Photos by Comedy Central, CBS and NBC

Out with David Letterman, Jon Stewart, Craig Ferguson, and Stephen Colbert. In with Trevor Noah, James Corden, Larry Wilmore, and Stephen Colbert. Lately, networks have been changing talk-show hosts faster than Zsa Zsa Gabor changed husbands. (That joke is our tribute to Johnny Carson.) The final piece falls into place tonight, when Colbert makes his CBS debut in Letterman’s old chair. After a long period of late-night firing, retiring, and hiring, it’s time to quantify the monologues and interviews, and crown the all-time kings (and a few queens) of talk. Our ranking includes some hosts who are entirely fictional, others who’ve expanded the job’s original boundaries through podcasting and satellite radio, and those who turned daytime TV into must-see entertainment. It does not, however, include John McEnroe, Magic Johnson, or Tony Danza; make no mistake, that was a conscious decision.

32. Jay Leno

First he elbowed aside David Letterman in order to inherit The Tonight Show from Johnny Carson (who clearly preferred Dave) in 1992. Then he ceded the throne to Conan O’Brien in 2009, only to return a few months later, when Conan’s ratings were iffy. For these two cutthroat moves, Jay Leno is despised by many comics. Howard Stern called him an “ass-kisser”; George Lopez labeled him “two-faced” and “the worst interviewer on TV”; and Arsenio Hall, Dennis Miller, and Craig Ferguson all mocked him. Leno began, in the 1970s, as a revered stand-up; “the best ever that I saw,” Letterman once avowed. But in Johnny’s chair, Leno became a consensus comedian whose O.J. Simpson and Lindsay Lohan jokes helped Americans nod off, like comedy chamomile. He was congenial without being charming, funny without being clever. Leno’s fans point to his endurance (22 years!) and popularity, but ask them to name a great show or moment and their eyes go blank. Jimmy Kimmel once said that Leno fans were “the stupid group,” and he summed up the argument against Jay: “He totally sold out. He was a master chef who opened a Burger King.” As Leno might point out, Burger King sells a lot of hamburgers. But that doesn’t mean they taste good.

31. Craig Kilborn

Yambo! Talk-show hosts aren’t supposed to be blond. Kilborn was a college basketball player, six-five, chiseled, and confident — Jon Stewart once described him as “Aryan” — who became Comedy Central’s biggest star when it was still airing crap like Gallagher specials and Win Ben Steins Money. He shepherded The Daily Show through its first incarnation as a silly, pop-culture-obsessed show — TV Guide once called it “TV’s hippest half hour” — then succeeded Tom Snyder at The Late Late Show for five years. The debate about Kilborn has always been, “Was he a frat-boy douchebag, or was he pretending to be a frat-boy douchebag as a piece of performance art?” Kilborn said, “It’s a character I play,” but it was often difficult to be sure. In 1997, the network suspended him for a week after he made trite, sexist jokes in an Esquire profile, about the “bitches” he worked with. Another time, he said about the show’s humor, “We want to avoid racism and being sexist. Well, for the most part.” And yet, his hair-gelled-news-anchor-mocking-hair-gelled-news-anchors tightrope shtick was appealing; comedian Janeane Garofalo admitted she’d had sexy dreams about him, and when asked in an interview if it was true, she replied, “Yes, unfortunately.”

30. Morton Downey Jr.

“I never did sleaze,” Morton Downey Jr. boasted, which is believable only if you think violence, hooliganism, misogyny, race-baiting, and demagoguery aren’t sleazy. Downey, who was born to a wealthy family, had a knockabout career singer, Top 40 DJ, political lobbyist before he started The Morton Downey Jr. Show at age 55, in October 1987, on local New York station WWOR-TV. He mixed his conservative politics with sexual titillation and the outrageous showmanship of pro wrestling. (Mort was the “Rowdy” Roddy Piper of talk shows.) He rapidly became a national phenomenon, beloved by angry, working-class whites and loathed by everyone else — a one-man tea party. The show went national: People tuned in to see him yell, “Sit down, you fat bitch,” and, “I would have kicked your fucking nuts out.” Guests backed out. Then TV stations did. In desperation, Downey a chain-smoking philanderer and habitual liar drew a swastika on his own forehead and claimed to have been assaulted by skinheads. No one believed his pathetic ploy. Ratings fell. Advertisers fled. His show was canceled. From start to finish, his tumultuous reign lasted less than two years.

29. Joan Rivers

Before she spit-roasted celebrity fashion don’ts or shamelessly harangued pompous actors on awards-show red carpets, the late Joan Rivers was a fearless, pioneering stand-up comedian whose showbiz breakthrough came, as it did for many comics, via Johnny Carson. Rivers first appeared on The Tonight Show in 1965; throughout the ‘70s and ‘80s, she regularly sat in for a vacationing Johnny before being promoted by the famously volatile Carson as an official guest-host in 1983. Rivers’s stand-up tagline was, “Can we talk?” and she was a enthusiastic interviewer with a big New Yawk yap, happy to play the fool to make her guests look their best. In 1986, when the burgeoning Fox network gave her The Late Show With Joan Rivers, competing directly against Carson (after NBC failed to consider her a suitable successor to him), Rivers became the first female late-night talk-show host. But with low ratings and a strained relationship between Rivers and Fox executives over the show’s eccentric direction, she was fired after just one year. Arsenio Hall would take over her role after a string of zany guest-hosts, and from ’89 to ’93, Rivers would try her hand at daytime hosting. Meanwhile, Carson never spoke to Rivers again, a knife-plunge that haunted her for the rest of her life. When her husband Edgar committed suicide in 1987, Carson did not contact her. “It was like Stalin had sent me to Siberia,” she told People. Despite Rivers breaking the glass ceiling nearly 30 years ago, late-night TV remains as much of a boys club today as it was during Carson’s martinis-and-strip-steak prime, and Rivers remains the only woman ever to host a network late-night talk show.

28. Space Ghost

And you thought Chevy Chase’s show was awful? Space Ghost was a vain, dimwitted Saturday-morning cartoon superhero who tried to revive his career with a talk show filmed in outer space, but his attempts to interview B-list celebrities were undermined by backstage bickering with his uncooperative sidekick, Zorak, and sarcastic director, Moltar, both of whom he’s imprisoned. With non sequiturs, outward hostility, and absurdist interludes, Space Ghost Coast to Coast mocked every talk show that preceded it, and the mesmerizing show’s cult success on Cartoon Network, where it debuted in 1994, led to the creation of the late-night Adult Swim block. The show’s appeal, aside from meta comedy (“Can you say ‘bang a dog up the ass’ on TV?” Space Ghost asks), was the sense that he was the only host who told the truth. “See you at the auto show,” he barked dismissively at Adam West, the has-been actor who played Batman in the ‘60s, something every host has surely fantasized about saying.

27. Mike Douglas

He always understood the appeal of his show: “I’m a square,” Douglas said. For 20 years, his low-pulse afternoon show comforted housewives and shut-ins, with occasional surprises. Douglas was a 1950s crooner whose semi-successful music career dwindled when rock and roll emerged; he was on the verge of becoming a real-estate broker before he was hired to host the tellingly titled Chicago talk-show Hi, Ladies! Affable and somewhat handsome, he was a reassuring relic of Middle American values; Roger Ailes, the devious Fox News president, was Douglas’s executive producer for a time. Douglas is now remembered chiefly for a week of shows in 1972, when John Lennon and Yoko Ono, determined to make radical politics less scary to Middle America, co-hosted with him and brought as guests Bobby Seale of the Black Panthers and antiwar activist Jerry Rubin, whom Douglas denounced (“My feelings are quite negative about this young man”) on air. “I don’t think The Mike Douglas Show will ever be the same,” Rubin declared, but he was wrong; Mike’s next co-hosts were Johnny Mathis and Eva Gabor.

26. Larry King

King’s great strength: He wasn’t very smart. With his clogged-nose Brooklyn accent, neck-chafing red suspenders, and eight marriages, he was easy to mock. At times, he seemed to be broadcasting from the activities room at Shady Pines Retirement Home he once confused Ringo Starr, who was sitting near him, with George Harrison, who was dead. King joined CNN in 1985, when it was a sketchy start-up, and as he became the biggest star on cable TV, he helped raise the network to prominence. He interviewed everyone, including eight presidents, and unlike Charlie Rose, who strives to demonstrate how insightful he is, King kept it simple: short, clear questions. Before he retired from Larry King Live in 2010, he said the greatest question an interviewer could ask is, “Why?” Many began to appreciate King only after they got to know his wretched replacement, Piers Morgan.

25. Regis Philbin and Kathie Lee Gifford

What do TV viewers want with their morning coffee and danish, after the kids have been packed off to school? Not social commentary or politics or jokes, even, the conventional wisdom goes. They — homemakers supposedly want chitchat. Mindless, good-natured, husband-and-wife-over-the-breakfast-table back-and-forth. For 12 years, no one did it with less mind or more good nature than gruff teddy bear Regis Philbin and tightly wound mama bear Kathie Lee Gifford. Regis, who’d served as Rat Pack jester Joey Bishop’s sidekick on a short-lived talk show in the ‘60s, had been co-hosting a version of the a.m. franchise since 1975, but it wasn’t until Kathie Lee joined him in ‘88 that the show, then renamed Live! With Regis and Kathie Lee, became a morning-TV bedrock. During her tenure, Gifford bravely grimaced through one tabloid scandal after another hubby Frank was caught having an affair; she was charged with using sweatshop labor to manufacture her Walmart clothing line and earned the sympathy of the female viewing audience for whom she was family (a crazy aunt, but still). The opening 15 or so minutes of Live! just Reege and Kathie Lee shooting the breeze about what they did last night, their families, which celebrity foibles deserved forgiveness, what really grinds their gears were flawless morning TV. Pass the cream, will ya, hon?

24. Zach Galifianakis

Nine weeks. That’s how long VH1 left Late World With Zach on the air in 2002. For Galifianakis, getting fired was like getting out of prison. On one episode, he admitted, “I can’t stand doing this,” which was evident to the dozens of people who were watching. Another night, he held up a sign that said, “I HAVE A SHOW ON A CHANNEL THAT THINKS CREED IS COOL.” Late World often settled for being a bizarre deconstruction of talk shows rather than actually funny, but six years later, Galifianakis found a perfect way to express his disdain for TV convention with Between Two Ferns, a tightly edited Funny or Die series in which he (convincingly) plays the inept, distracted, hostile host of a cable-access show who somehow lands famous guests like President Obama and Brad Pitt. Galifianakis implies that Christoph Waltz has a Mein Kampf tattoo, persuades Amy Adams to read from a script that says, “Don’t you ever fart on my tits again,” and asks Natalie Portman if he can smell her dog’s penis. Jealous yet, VH1?

23. Merv Griffin

When CBS launched its first late-night talk show in 1969 to battle the almighty Carson, it wanted Merv Griffin, who had a hit afternoon show. He said he’d do it only if CBS paid him double what Carson was earning. To Merv’s shock, CBS agreed. And when it fired him three years later, he launched a syndicated talk show, which ran until 1986 and made him a TV sultan. Griffin began his career as a pop crooner, but his great gift was business: He created Jeopardy! (and composed “Thinking,” the show’s famous theme song) and Wheel of Fortune, acquired a hotel empire, and amassed a fortune estimated at $1 billion. Because he was dapper and exclaimed “Ooooh” frequently, Griffin (who was outed after he died) was too easily mocked; in an SCTV spoof, Rick Moranis as Merv tells Yasser Arafat, “That’s a marvelous hat you’ve got on.” Griffin sometimes got his guests drunk before the show, and he wasn’t averse to alcohol himself. But whether he was talking to Martin Luther King or Marie Osmond, he remained a smooth, silver-tongued emcee. Richard Nixon once angrily walked off the show during a commercial break, which delighted Griffin, even though he was a staunch Republican.

22. Barth Gimble

Barth Gimble was a TV host in Miami who fled Florida to escape legal charges that he swore involved entrapment. Stranded in Fernwood, Ohio, Barth hosted a low-budget local show, Fernwood 2 Night. The one-season series, which made its syndicated debut in 1977, billed itself as the first totally fictional talk show on television and won a cult following. Martin Mull brought mustachioed smarm to the role of Gimble, a condescending blowhard stuck in a hick town, and Fred Willard (setting the tone for the rest of his career) played oblivious sidekick Jerry Hubbard. The show mocked midwestern small-mindedness; on the first episode, in a segment called “Talk to a Jew,” Barth explained that Fernwood townsfolk have “never seen a real, live Jew,” and invited them to phone in with questions. “Ignorance often breeds contempt and prejudice,” Gimble declared, and the locals called to ask his Jewish guest why he wan’t wearing a beanie and when the next Barbra Streisand movie was coming out. So much for eradicating ignorance.

21. The View (Seasons 6–9: Barbara Walters, Joy Behar, Meredith Vieira, Star Jones, Elizabeth Hasselbeck)

Which championship basketball team does The View’s classic lineup most closely resemble? We’re going with the 1996 Chicago Bulls: Joy Behar is Scottie Pippen, Star Jones is Dennis Rodman, Meredith Vieira is Toni Kukoč, Elizabeth Hasselbeck is also Dennis Rodman (okay, it’s not a perfect analogy), and G.O.A.T. Barbara Walters is Michael Jordan and Phil Jackson rolled into one. With the 2014 retirement of Walters at the close of The View’s 17th season, the organization has been forced to rebuild remember that seemingly promising but ultimately disappointing draft pick of Rosie Perez? adding fading all-star Rosie O’Donnell and (now-departed) rookie Republican Nicolle Wallace to a squad anchored by crafty vet Whoopi Goldberg.

20. Arsenio Hall

When Bill Clinton appeared on the syndicated Arsenio Hall Show in June 1992, his presidential election was anything but assured. George H.W. Bush was the Republican incumbent, and independent Ross Perot, who’d recently announced his candidacy, was grabbing headlines. Clinton’s advisers needed to reestablish the governor’s bona fides to young voters, and Hall and his hit show were a phenomenon: Not only was it the first national late-night show hosted by an African-American, but one proudly borne of the hip-hop generation. In Risky Business shades borrowed from an aide, Clinton played saxophone with the band (Elvis’s “Heartbreak Hotel”) to a rousing chorus of woof-woof-woofs from the audience, then joked with Hall about his famous “I didn’t inhale” cop-out, explaining that smoking pot “was another one of those things I tried to do in life and failed.” Clinton’s gambit worked; the appearance made headlines, and the first “MTV president” was handily elected in November. As for Hall, his mix of new-jack swagger and Friars Club schmaltz made him a dorm-room favorite from ‘89 until 1993, when Letterman took over CBS’s 11:30 slot and hijacked Hall’s audience. A year later, Hall’s show was canceled. Near the end of his second term, Clinton phoned Hall out of the blue and invited him to a soccer game. “Why me?” Hall asked. “You got me elected,” Clinton replied.

19. Bill Maher

Earlier this year, when he called American Sniper a film about “a psychopath patriot,” Maher reminded us that the essence of comedy is disruption and dissent. Consider this: After 9/11, comedy rolled into a fetal position. Leno and Letterman got timid. Jon Stewart cried. That week, on his ABC show Politically Incorrect, Maher said the 9/11 terrorists weren’t cowardly, but the U.S. response was: “Lobbing cruise missiles from 2,000 miles away, that’s cowardly.” Too soon? The Bush White House objected, sponsors fled, ABC fired him, and Maher moved to HBO, where, under the name Real Time, he’s unconstrained by FCC rules against curse words and weed jokes. Maher has contempt for modern TV “programs like The Tonight Show are no longer real talk, just cogs in the publicity mill,” he told Playboy in the midst of Politically Incorrect’s mid-’90s Comedy Central run and with his hot-button topics and bickering guests, he’s brought back articulate conversation while adding the possibility of violence: Tune in and find out whether Spike Lee punches Tucker Carlson in the face. Maher has a gift for getting to the root of current events, as when he referred to the Bill Clinton–Monica Lewinsky affair as “ten instances of prison sex.” But we still wish he’d cut his fucking mullet.

18. Jimmy Kimmel

Kimmel is an oddity in the modern-day late-night wars. Neither puppy-dog cute and earnest like Jimmy Fallon, nor a graceful comic actor like Stephen Colbert, nor even a corn-fed smart-aleck like David Letterman, Kimmel is more average man than everyman, a fast-witted shlub whose total lack of fealty toward celebrity may be his strongest suit. Since trampolining from co-host of Comedy Central’s puerile Man Show to his late-night Jimmy Kimmel Live! slot on ABC (where he retired Ted Koppel), Kimmel has established himself, in the show’s first 30 minutes, at least, as a reliably funny, occasionally cutting presence. The pretaped bits in particular, built for social-media sharing, are frequently hilarious and skewering: the star-studded mock–music video “I’m Fucking Matt Damon,” and the recurring “Celebrities Read Mean Tweets” (Jennifer Garner: “Jennifer Garner looks like a duck’s vagina”). If Fallon strives for lovable, Kimmel settles for likable a good guy whose real-life cousins and uncles are part of the show’s cast and spirit. Just be sure to skip the show’s second half: Kimmel’s a hopelessly feckless interviewer.

17. Jack Paar

Soon after he became host of The Tonight Show in the summer of 1957, Paar was the first king of late night. The key to his appeal, said Dick Cavett, “was danger.” Paar cried on-camera, spoke out about politics, beefed with critics, and one night, annoyed with actor Mickey Rooney, threw him off the show. “I wanted it to feel like theater,” he said, which was an even bigger challenge because his show was an hour and 45 minutes long. Friends described him as quixotic, neurotic, and unstable, a raw nerve soaked in nitroglycerin. (His successor, Carson, called Paar an “emotional, crazy man.”) A stutterer in childhood and a high-school dropout, Paar toiled in radio, films, and on TV, racking up a remarkable number of canceled shows before his Tonight reign, which lasted less than five years. He was a great monologuist, possibly because he performed them without cue cards or a TelePrompTer, and a probing interviewer more interested in conversation than in punch lines. When NBC prudishly censored a harmless toilet joke he told, Paar quit in protest the next night, tearing up, he walked offstage during his own show, leaving his announcer to finish the remaining hour and 16 minutes. And you think Letterman was snippy?

16. Tom Snyder

Tom Snyder’s late-night one-on-one interview show, Tomorrow, was such a cultural touchstone of the ‘70s that Dan Aykroyd’s impression of Snyder became an early staple of Saturday Night Live. Snyder was a caricature in human form: tall, pompous, with unruly sideburns and a comb-over that began just above his right ear. But his abrasive personality exacerbated by occasional hangovers suited the late hour. Snyder was a blowhard who valued his own opinions more than his guests’ and laughed hardest at his own jokes, but to his credit, he treated Don Rickles with the same gruff bonhomie as he did John Lennon (in his last-ever interview). A career news reporter, Snyder was square and insistent, whether chiding a dominatrix (“To me, this is sick”) or Charles Manson, at whom he barked, “Stop the hogwash.” NBC canceled Tomorrow and replaced him with Letterman, who more than a decade later showed his respect by hiring Snyder at CBS as the host of the then-new Late Late Show. At a press conference, when Snyder asked for advice, Letterman snapped, “Do something about the hair.”

15. Ellen DeGeneres

Where women once swore allegiance to Oprah’s self-actualized, inspirational talk-therapy, their new daytime heroine is more BFF than shrink. On The Ellen DeGeneres Show, there are no lifestyle gurus, no abused spouses, no size 22s hoping to fit into a size-4 wedding gown. Instead, there’s the host, in tailored menswear and sneakers, dancing with her audience to feel-good ‘80s R&B, presiding over smiley-faced party games and comedy bits, and cheerfully goading celebrities even presidents into goofing around with her. “Most comedy is based on getting a laugh at somebody else’s expense, and I find that’s just a form of bullying,” she’s explained, and she’s mostly stuck to that, even when judging American Idol or hosting the Oscars. One big difference between DeGeneres and most (notoriously paranoid) talk-show hosts: She talks freely about her love life, especially since marrying actress Portia de Rossi in 2008. It’s an unmistakable sign of social progress that, in 2015, Middle America rates Ellen’s home life somewhere between idyllic and whatever.

14. Phil Donahue

“If there had been no Phil Donahue show, there would be no Oprah Winfrey show,” Oprah wrote in 2002, which makes Donahue the most influential figure in daytime-TV history. His Phil Donahue Show ran nationally from 1970 to 1996 and frequently tackled important, sometimes taboo social issues: race, sexuality, and, most famously, the covering up of sexual abuse by the Catholic church. Competing against soap operas and game shows, Donahue took the concerns and interests of women seriously. He was the first talk-show host to solicit questions from his studio audience for his guests, who included everyone from Ayn Rand to economist Milton Friedman to Louis Farrakhan. In the ‘90s, Donahue clones from Sally Jessy Raphael to Jerry Springer would dumb down and tabloid up his format, and his run soon ended. Donahue may have also been the most far-left host in TV history; during a brief prime-time comeback on MSNBC, he was fired, in large part, for his criticism of the first Gulf War.

13. Jimmy Fallon

“I thought the smart move was to drop down a generation,” SNL producer Lorne Michaels told New York, explaining his decision to make Jimmy Fallon the sixth host of The Tonight Show. Twelve years younger than Conan and seven years Kimmel’s junior, 40-year-old Fallon breaks with recent comedy trends by showing no interest in irony, meta comedy, or even being cheeky. “I never do anything sneaky or try to make guests look bad,” the chipper Queens-born comedian told New York last year. Though he appears incapable of having a conversation without giggling, he’s singlehandedly revived late night. How? By reimagining the audience and the way they consume media: on their phones, bored at work, skimming Facebook. So Fallon’s interviews are primarily excuses to get A-list stars to do fun, dumb shit Jennifer Aniston plays “Lip Flip,” Gwyneth Paltrow sings Broadway versions of hip-hop hits, Lena Dunham and J.K. Simmons team for Pictionary and Fallon’s frequently awesome musical impersonations and bits, with help from his swaggering and versatile house band the Roots, rack up tens of millions of YouTube views. Fallon may be as edgy as a box of kittens, but his audience is nearly double that of runner-up Jimmy Kimmel, and top celebs flock to the comfort of his sofa. In today’s late-night wars, nice guys finish first.

12. Dick Cavett

Before celebrities occupied the entirety of American cultural coverage, talk shows often booked guests who were authors or philosophers. No host was more identified with lofty conversation than Dick Cavett, who was as influential (if not nearly as popular) as Johnny Carson. The midwestern son of two teachers, Cavett had a low-level job at Time when he nervily infiltrated NBC’s offices and handed an envelope of jokes to Jack Paar, who hired him as a writer. Cavett worked for Carson and Merv Griffin, and when ABC gave him a show in 1969, an AP story said he was “noted for low-keyed humor and sophisticated barbs.” Unlike most other hosts, he wasn’t apolitical, and his support for John Lennon infuriated Richard Nixon so much, the president asked an aide if there was a way “we can screw” Cavett. Words like erudite and intellectual stuck to him, but his show’s most memorable moments were loud and tense: writers Norman Mailer and Gore Vidal trading murderous insults, Georgia’s pro-segregation governor Lester Maddox walking off the set because the host called his supporters “bigots,” or Cavett telling LSD guru Timothy Leary he was “full of crap.” To alienate both Leary and Nixon now, that’s an accomplishment!

11. Craig Ferguson

When Johnny Carson died, Ferguson had been hosting The Late Late Show for less than three weeks. He was already working without a house band, and then he decided to do away with other talk-show conventions most important, no prepared monologue and no staged questions with guests. Later, motivated by what he called a “deconstructionist contempt” for talk shows, he introduced his sidekick, Geoff, a gay robot with a mohawk. From 2005 until last December, Ferguson was the best host on late-night TV, through a mix of intelligence, honesty, dont give a fuck swagger, and wit. “If late night is a club, I don’t want to be a member,” he said. A Scottish-born comedian picked by Peter Lassally, the TV legend who produced Carson and Letterman, Ferguson fostered anarchy, flirted joyfully with actresses, impersonated Sean Connery, played harmonica, and had memorable serious moments: a lengthy interview with Bishop Desmond Tutu, poignant eulogies for his parents, a discussion of his alcoholism, and a pledge not to make hack jokes about celebrities in legal trouble ([cough] Jay Leno [cough]), because comedy should attack the powerful and not the vulnerable.

10. Terry Gross

Terry Gross, the long-running host and executive producer of NPR’s “Fresh Air,” is a boss: a fearless, legendarily well-prepared, intellectually omnivorous interviewer whose needle-sharp questions often lead to enlightening, occasionally heated exchanges with cultural and political icons. Bill O’Reilly stormed out of an interview, and Hillary Clinton got huffy when pressed on gay marriage. Gross’s greatest moment, though, came in a steel-cage match with Kiss’s face-painted vulgarian Gene Simmons, in 2002. Gross tossed grenades, and Simmons swallowed them whole. Gross: “Let’s get to the studded codpiece. Do you have a sense of humor about that?” Simmons: “No … It holds in my manhood … Otherwise it would be too much for you to take. You’d have to put the book down and confront life. The notion is that if you want to welcome me with open arms, I’m afraid you’re also going to have to welcome me with open legs.” Gross: “That’s a really obnoxious thing to say.” And many exchanged insults later, finally, Gross: “My impression is you don’t have much sympathy for anyone. You’re just so deep into yourself.” Terry Gross: She gives no fucks.

9. Conan OBrien

Here’s how dire it was for Conan O’Brien: Bob Denver canceled. When a sitcom actor 35 years past his prime can’t be bothered to sit in your show’s padded armchair, you’re circling the drain. O’Brien was a top comedy writer with little performing experience when NBC hired him to replace David Letterman on Late Night in 1993, after Garry Shandling, Dana Carvey, and half of Hollywood turned down the job. O’Brien was jumpy and overeager, and when ratings dropped, the network fired him, only to realize they didn’t have anyone to take his place. David Letterman visited the show and gave it his imprimatur, and ratings slowly rose. O’Brien’s plan was to stage a traditional talk-show, but with all the elements twisted; hence, the Masturbating Bear, Pimpbot, and, uh, Andy Richter. Eventually, his ratings were good enough that NBC promised him the network’s prize job, hosting The Tonight Show. He lasted only a few months barely long enough to shoot a wax model of Tom Cruise out of a cannon and was pushed out when Jay Leno agreed to sit his fat ass back in the big chair. Though a naturally easygoing man, he was now angry, which added a new and wonderful danger to his final NBC shows, including the piercing jibe, “I just want to say to the kids out there, you can do anything you want in life. Unless Jay Leno wants to do it, too.” Maybe we need to reconsider who won that battle Leno is off the air, and O’Brien is still on, as is the Masturbating Bear.

8. Stephen Colbert

The most exciting moment in late-night television since a gap-toothed Indiana weatherman slid into late night on CBS will take place on September 8, 2015, when Stephen Colbert takes over for said Hoosier, David Letterman, as host of The Late Show. Frankly, Colbert is too brilliant a performer to be a major-network late-night talk-show host in 2015 he makes Fallon and Kimmel look like morning-zoo jocks in comparison but his error in judgment is our good fortune. For ten years on The Colbert Report, he turned his bloviating right-wing newsman character, fake-mourning the loss of the white man’s paradise, into a fully dimensional, even lovable guy more Homer Simpson than Peter Griffin. In real life, Colbert is a science-fiction-reading, Sunday-school-teaching father of three with an abiding sense of social justice, as evidenced in his testimony before a congressional subcommittee on the rights of migrant workers (“I like talking about people who don’t have any power”). Most of all, though, Colbert is wickedly funny, and seems too smart to play dumb, even for a major-network paycheck. Or at least we can hope.

7. Larry Sanders

What Spinal Tap is to heavy metal, Garry Shandling’s brilliant HBO workplace comedy The Larry Sanders Show is to late-night talk. Shandling knew talk shows; after a stint as a sitcom writer, he turned to stand-up, with successful appearances on The Tonight Show leading to a gig as one of Johnny’s recurring guest-hosts in the ‘80s. In 1992, Shandling mined that desk gig to co-create Sanders for HBO, lampooning with deadpan accuracy the glorious vanities of late night. Starring Shandling as Sanders (the putative Carson), Rip Torn as Artie (Carson’s producer Fred de Cordova), and Jeffrey Tambor as mewling Hank “Hey Now” Kingsley (the Ed McMahon–like sidekick), the show was nominated for 56 Emmys during its six-year run. Today, with more late-night options and dwindling big-three-network audiences, celebrities no longer have to genuflect before talk-show hosts as they did to Sanders, but Shandling’s skewering of showbiz narcissism and insecurity remain eternal.

6. Oprah Winfrey

Oprah by the numbers:

Years The Oprah Winfrey Show aired: 25 (1986–2011)
Average number of weekly viewers: 40 million
Number of pounds of fat she rolled out in a red wagon, equal to the weight she lost on the liquid Optifast diet, in 1988: 67
Number of Pontiac G6 automobiles given away to audience members during 2004’s season premiere: 276 (“You get a car! And you get a car! And you get a car! EVV-ree-BAH-dee gets a car!”)
Number of times Tom Cruise bounced up and down on Oprah’s sofa to celebrate his love for Katie Holmes in a 2005 episode: 2
Number of books selected as part of Oprah’s Book Club: 65
Number of TV hosts whose careers were launched by appearances on Oprah: 7 (Dr. Phil, Gayle King, Dr. Oz, Suze Orman, Iyanla Vanzant, Rachael Ray, Nate Berkus)
Oprah’s estimated net worth: $2.9 billion

5. Marc Maron

Self-destructive stand-up turned failed left-wing radio host Marc Maron was just another bitter, neurotic, narcissistic, middle-aged comic before he began broadcasting a twice-weekly long-form interview podcast called “WTF,” recorded in his Highland Park, California, garage. He’s still neurotic, thankfully (and reliably funny), but the bitterness has subsided, mostly due to the enormous success of his podcast, and the narcissism has given way to a profound curiosity about and empathy for the inner lives of artists: fellow comedians, as well as actors, directors, and musicians (recent guests run from Brillo-headed nonagenarian comic Marty Allen to alt-comedy nerd Barack Obama). No one gets more out of his guests than Maron, whose now-familiar emotional touchstones family background as class determinant, art as the pursuit of truth, self-acceptance and forgiveness give every interview a sweetness and depth without equal. Slate ranked the 25 greatest podcast episodes of all time; Maron’s two-plus-hour talk with frenemy Louis C.K., who broke down and cried while talking about the birth of his daughter, was the no-brainer choice for No. 1. That, and the 634 other “WTF” episodes, are as good as a talk show gets.

4. Jon Stewart

He was the booby prize. Comedy Central didn’t want to lose Craig Kilborn, the original host of The Daily Show, and after CBS lured Kilborn away with network-size money in 1999, the cable channel sued him for breach of contract. Then they turned to Jon Stewart, who’d had more success as a fake replacement talk-show host on The Larry Sanders Show than he’d had hosting an actual talk show for about 18 months in the mid-’90s, mostly on MTV. Turned out Stewart was way funnier when he wasn’t pretending to care about Blind Melon or Bronson Pinchot. Starting with “Indecision 2000,” the former stand-up comic exposed what Tom Brokaw calls the “absurdities, hypocrisies, [and] juvenilia” of the political charade. Satire was too weak a word — when Stewart attacked targets small (Chris Wallace) or big (Douglas Feith), there was an actual punch to his punch lines. Stewart’s “fake news” show offered more analysis and courage than any other TV program, and with his array of blank stares, double takes, and openmouthed, bug-eyed outrage, he became the Meryl Streep of reaction shots. Fittingly, the booby prize went on to win the Thurber Prize for American Humor.

3. Johnny Carson

When Jack Paar left The Tonight Show, NBC offered the gig to Carson, a comedian in his late 30s who was hosting a game show. He turned it down. The job came with too much pressure “People said, ‘Nobody will ever replace Paar,’” Carson recalled. Now they say the same about Johnny. “For a whole generation, he kind of established the model of how cool guys behaved,” said Letterman, a disciple. In the ‘60s, ‘70s, and ‘80s, there were no late-night wars: From Les Crane to Joan Rivers, everyone who challenged Carson fell quickly. He transformed Tonight into the best job on TV, one his successor would fight and scheme to have. With his Malibu tan and Burbank wisecracks, Carson did more than anyone else to make L.A. a brand. And though his private life was a mess four wives, an ocean of booze, strained relationships with his kids on camera, he made comedy seem effortless, like his role models Bob Hope and Jack Benny. He was a model of understatement, relying on a subtle wink, a skeptically raised eyebrow, a behind-the-beat quip. For 30 years, he was the center of American culture. How influential was he? “Everybody else who’s doing a show, myself included, we’re all kind of secretly doing Johnny’s Tonight Show,” Letterman admitted in his on-air eulogy of Carson in 2005.

2. David Letterman

Midnight TV is meant to pacify you, offering a sedative chuckle to help you sleep soundly. David Letterman introduced the prospect of discomfort. “Most TV is totally unsurprising,” he once said, adding that he wanted viewers “to look at each other and say, ‘What the hell was that?’” Stupid Pet Tricks were clever, Larry “Bud” Melman was annoying, and the great attraction was the chance that Dave would go off on a guest. He found his feet soon after Late Night With David Letterman debuted in 1982, during an interview with actress Nastassja Kinski, whom he made uncomfortable by repeatedly asking about her weird hairstyle. “What’s the matter with you?” she sniffed. Then came a timeline of what the hell? moments, commemorated on YouTube: Crispin Glover, Oliver Reed, Drew Barrymore, Madonna, Cher (who called him an asshole), John McCain in absentia, Joaquin Phoenix, Farrah Fawcett. Over the years, he also added heartfelt moments his first shows after 9/11 and his heart surgery, the night he confessed to having sex with staffers but he still responded irascibly to showbiz b.s. When Paris Hilton grew tired of his questions about her jail sentence related to drinking and driving and said, “I don’t really want to talk about it,” Dave mercilessly replied, “This is all I want to talk about.”

1. Howard Stern

Wilmer Valderrama bragged about deflowering Mandy Moore. Megyn Kelly discussed her husband’s dick size. Billy Joel reminisced about doing heroin. For over 30 years, Howard Stern’s calling and gift has been getting his guests, many wildly famous, to talk freely about all the things they’d rather not talk about. Of course there’s sex so much sex but there’s also drugs and money, which, for most celebrities, are far more taboo, and marriage and work anxiety and family and vanity. If there’s one theme running through the thousands upon thousands of interviews Stern has conducted, it’s that he hates a phony. Sometimes that can be a limited, teenaged lens through which to view the world, but Stern’s bullshit detector is what his fans love most about him, and his own neuroses and discomfort more than balance out the self-righteousness. “In real life,” Stern says, “I barely know how to socialize,” and his forays into TV and movies have largely been busts. But when the on-air light goes on, five mornings a week these days on SiriusXM, he’s the best that ever was.

The 32 Greatest Talk-Show Hosts Ever, Ranked