# List of Playboy interviews

The Playboy interview became a regular feature of the magazine in 1962 and set a high standard for periodical journalism. AP News called the feature "models of the art form", stating that "Playboy's long and searching conservations are remarkable for the people who spoke to the magazine and for what they said." Booklist called the Playboy interview "the gold standard for in-depth discussion with leading cultural figures".
The conversations with artists, athletes, business leaders, and political figures have been referenced by mainstream publications such as AP News, Billboard, CNN, Los Angeles Times, The Paris Review, Slate, Time, Variety, Vice, and The Washington Post as a benchmark for in-depth interviews. Publishers Weekly commented on the feature's ability to go further than a normal magazine interview: "Since the interviews have no length restriction, interviewers are able to probe deep into their subjects and allow them to ramble expansively."
The Los Angeles Times described the subjects as coming from "all across the cultural spectrum: entertainment, politics, literature", calling them "open-ended, sprawling, a kind of 'Charlie Rose Show' of the printed page", and Playboy's format served as inspiration for Rolling Stone editor Jann Wenner when he designed his own magazine's approach to interviews.
The Playboy interview with candidate Jimmy Carter is regarded by many to have influenced the 1976 presidential election, and the interview with John Lennon before his death (later published as a standalone book) is referenced in several retrospective articles by other media. Playboy's interview with pop singer Azealia Banks caused controversy for her open criticism of the American public.
Selected interviews have been published as mass-market collections, including The Playboy Interview (1981) and The Playboy Interview Volume II (1983). In 1992, a large-format book The Playboy Interview: The Best Of Three Decades 1962-1992, was released with a foreword by CBS journalist Mike Wallace.
Dark Horse published five collections of the interviews from 2006 to 2008: "The Comedians", "Movers and Shakers" (business), "The Directors", "Larger Than Life" (high-profile celebrities), and "They Played The Game" (sports). In a review of this series, the Directors Guild of America said, "The Playboy face-to-face encounter is remarkable", and "the lengthy, in-depth interviews are well researched and more penetrating than standard-issue media chatter."
The following people have been featured in Playboy magazine as the subject of the full-length interview or the 20Q (Twenty Questions) section.

## 1960–1969

| | | January | February | March | April | May | June | July | August | September | October | November | December |
| 1962 | Interview | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | "Playboy Interview" begins September 1962: | Miles Davis | (none) | (none) | Jackie Gleason |
| 1963 | Interview | (none) | Frank Sinatra | Bertrand Russell | Helen Gurley Brown | Malcolm X | Billy Wilder | (none) | (none) | Richard Burton | James Hoffa | Albert Schweitzer |
| 1964 | Interview | Vladimir Nabokov | (none) | Ayn Rand | Jean Genet | (none) | Ingmar Bergman | Salvador Dalí | Dick Gregory | Henry Miller | Cassius Clay | George Wallace | Ian Fleming |
| 1965 | Interview | Martin Luther King | The Beatles | (none) | Art Buchwald | Jean-Paul Sartre | Melvin Belli | Marcello Mastroianni | Robert Shelton | Peter O'Toole | Madalyn Murray | Sean Connery | Al Capp |
| 1966 | Interview | Princess Grace | Federico Fellini | Bob Dylan | George Lincoln Rockwell | Arthur Schlesinger, Jr. | Mike Nichols | Ralph Ginzburg | H. L. Hunt | Timothy Leary | Mel Brooks | Norman Thomas | Sammy Davis Jr. |
| 1967 | Interview | Fidel Castro | Mark Lane | Orson Welles | Arnold Toynbee | Woody Allen | (none) | Michael Caine | F. Lee Bailey | John V. Lindsay | Jim Garrison | Michelangelo Antonioni | Johnny Carson |
| 1968 | Interview | Norman Mailer | Jim Brown | Truman Capote | Charles Percy | Masters and Johnson | John Kenneth Galbraith | Paul Newman | (none) | Stanley Kubrick | Ralph Nader | Don Rickles | (none) |
| 1969 | Interview | Martin Luther King Jr. | Mort Sahl | Marshall McLuhan | Allen Ginsberg | Bill Cosby | Gore Vidal | Rod Steiger | Ramsey Clark | (none) | Rowan and Martin | Jesse Jackson | Joe Namath |

## 1970–1979

| | | January | February | March | April | May | June | July | August | September | October | November | December |
| 1970 | Interview | Raquel Welch | (none) | Ray Charles | Mary Calderone | William F. Buckley Jr. | Tiny Tim | Joan Baez | Paul R. Ehrlich | Peter Fonda | William Kunstler | Elliott Gould | Robert Graves |
| 1971 | Interview | (none) | Tom Murton | Dick Cavett | (none) | John Wayne | Albert Speer | John Cassavetes | George McGovern | Jules Feiffer | Charles Evers | Allen Klein | Roman Polanski |
| 1972 | Interview | Germaine Greer | R. Buckminster Fuller | Saul Alinsky | Jack Nicholson | Howard Cosell | Jackie Stewart | Anthony Herbert | Sam Peckinpah | Bernadette Devlin | Meir Kahane | Jack Anderson | Yevgeny Yevtushenko |
| 1973 | Interview | Carroll O'Connor | Milton Friedman | Joe Frazier | Tennessee Williams | Huey Newton | Walter Cronkite | Kurt Vonnegut Jr. | David Halberstam | (none) | Pete Rozelle | James Dickey | Bob Hope |
| 1974 | Interview | Hugh Hefner | Clint Eastwood | Groucho Marx | Jane Fonda, Tom Hayden | Henry Aaron | Elmo Zumwalt | Barry Commoner | Erich von Däniken | Anthony Burgess | Al Goldstein | Hunter Thompson | Robert Redford |
| 1975 | Interview | John Dean | Mel Brooks | Billie Jean King | Dustin Hoffman | William E. Simon | Joseph Heller | Francis Ford Coppola | Philip Agee | Erica Jong | Cher | Muhammad Ali | Jimmy Hoffa |
| 1976 | Interview | Elton John | James Caan | Norman Lear | Jerry Brown | Abbie Hoffman | Sara Jane Moore | Karl Hess | Robert Altman | David Bowie | Roone Arledge | Jimmy Carter | O. J. Simpson |
| 1977 | Interview | Alex Haley | Keith Stroup | Pat Moynihan | Gary Gilmore | Cast of Saturday Night Live | Robert Blake | Andrew Young | Henry Winkler | James Earl Ray | Barbra Streisand | Henry Kyemba | John Denver |
| 1978 | Interview | Playboy Panel: UFOs | Don Meredith | Bob Dylan | David Frost | Anita Bryant | George Burns | William Colby | Ted Turner | Sylvester Stallone | Dolly Parton | Geraldo Rivera | John Travolta |
| 1978 | 20Q | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | "20Q" begins October 1978: | Cheryl Tiegs | (none) | (none) |
| 1979 | Interview | Marlon Brando | Neil Simon | Ted Patrick | Malcolm Forbes | Wendy/Walter Carlos | Dennis Kucinich | Joseph Wambaugh | Edward Teller | Pete Rose | Burt Reynolds | Masters and Johnson | Al Pacino |
| 1979 | 20Q | (none) | (none) | (none) | (none) | Dan Rather | (none) | (none) | Frank Langella | (none) | (none) | (none) | (none) |

## 1980–1989

| | | January | February | March | April | May | June | July | August | September | October | November | December |
| 1980 | Interview | Steve Martin | Patrick Caddell | Terry Bradshaw | Linda Rondstat | Gay Talese | John Anderson | Bruce Jenner | William Shockley | Roy Scheider | G. Gordon Liddy | Larry Hagman | George C. Scott |
| 1980 | 20Q | (none) | (none) | Shelley Hack | (none) | (none) | (none) | George Hamilton | (none) | (none) | (none) | Michael Douglas | Truman Capote |
| 1981 | Interview | John Lennon / Yoko Ono | Tom Snyder | James Garner | Ed Asner | Elisabeth Kubler-Ross | Steve Garvey | Robert Garwood | George Gilder | James Michener | Donald Sutherland | Oriana Fallaci | Henry Fonda |
| 1981 | 20Q | (none) | (none) | Lauren Hutton | (none) | John DeLorean | Jack Lemmon | (none) | Joan Rivers | (none) | (none) | (none) | John Kenneth Galbraith |
| 1982 | Interview | George Carlin | Lech Walesa | Patricia Hearst | Edward Koch | Billy Joel | Sugar Ray Leonard | Bette Davis | Akio Morita | Cheech and Chong | Robin Williams | Luciano Pavorotti | Julie Andrews, Blake Edwards |
| 1982 | 20Q | John Matuszak | Karen Allen | Louis Rukeyser | James Woods | SCTV | Brandon Tartikoff | Stevie Nicks | Mariette Hartley | Tom Petty | John Le Boutillier | Frank and Moon Unit Zappa | (none) |
| 1983 | Interview | Dudley Moore | Gabriel García Márquez | Sam Donaldson | Paul Newman | Ansel Adams | Stephen King | Earl Weaver | Ted Turner | The Sandinistas, Daniel Ortega | Cast of Hill Street Blues | Kenny Rogers | Tom Selleck |
| 1983 | 20Q | Herschel Walker | Yakov Smirnoff | Arthur Jones | Al McGuire | Charlton Heston | Debra Winger | Carrie Fisher | Jan Stephenson | Randy Newman | Joe Piscopo | Bubba Smith | (none) |
| 1984 | Interview | Dan Rather | Paul Simon | Moses Malone | Joan Collins | Calvin Klein | Jesse Jackson | Walid Jumblatt | Bobby Knight | Shirley MacLaine | David Letterman | José Napoleón Duarte | Paul and Linda McCartney |
| 1984 | 20Q | (none) | Shelley Long | (none) | Martin Mull | (none) | Siskel and Ebert | Fran Lebowitz | Kurt Russell | (none) | Jack LaLanne | Leigh Steinberg | (none) |
| 1985 | Interview | Goldie Hawn | Steve Jobs | Cast of 60 Minutes | Wayne Gretzky | Boy George | Sparky Anderson | Rob Reiner | Fidel Castro | John Huston | John DeLorean | Sting | Bill Cosby |
| 1985 | 20Q | Diane Lane | Brian De Palma | Bob Giraldi | Joel Hyatt | Marvin Hagler, Thomas Hearns | Tom Watson | Jamie Lee Curtis | Ron Howard | Billy Crystal | Rosanna Arquette | Don Johnson, Philip Michael Thomas | Huey Lewis |
| 1986 | Interview | Ruth Westheimer | Michael Douglas | Sally Field | Jeffrey MacDonald | Kathleen Turner | Kareem Abdul-Jabbar | Arthur C. Clarke | Jackie Gleason | Carl Bernstein | Phil Collins | Joan Rivers | Bryant Gumbel |
| 1986 | 20Q | Jay Leno | Anthony Pellicano | David Byrne | (none) | Kim Basinger | Al Unser, Sr., Al Unser, Jr. | Tom Cruise | Sigourney Weaver | Gregory Hines | Jim McMahon | David Horowitz | Koko |
| 1987 | Interview | Don Johnson | Mickey Rourke | Lionel Richie | Louis Rukeyser | Prince Norodom Sihanouk | Whoopi Goldberg | Wade Boggs | Imelda and Ferdinand Marcos | John Sculley | General Richard Secord | Daniel Ortega | Gore Vidal |
| 1987 | 20Q | Max Headroom | Ed Begley Jr. | Bob Vila | Rae Dawn Chong | Barbara Hershey | Michael J. Fox | Garry Shandling | David Lee Roth | Penn And Teller | Bob Uecker | Kelly McGillis | Justine Bateman |
| 1988 | Interview | Arnold Schwarzenegger | Oliver Stone | Billy Crystal | Tom Clancy | Don King | Chevy Chase | Paul Hogan | Harvey Fierstein | Yasser Arafat | Roger Craig | Bruce Willis | Cher |
| 1988 | 20Q | Susan Dey | Harold Washington | Tom Waits | Harrison Ford | Teri Garr | Theresa Russell | Judge Reinhold | Harry Edwards | Tracey Ullman | Morton Downey Jr. | John Cleese | Gene Simmons |
| 1989 | Interview | Robert De Niro | Bob Woodward | Tom Hanks | The I.R.A. | Susan Sarandon | Edward James Olmos | Barry Diller | John Cougar Mellencamp | Keith Hernandez | Keith Richards | Garry Kasparov | Candice Bergen |
| 1989 | 20Q | (none) | Andrea Marcovicci | Fred Dryer | Mario Lemieux | Richard Lewis | Nicolas Cage | William Shatner | John Candy | Jeff Daniels | Geena Davis | Bonnie Raitt | Patti D'Arbanville |

## 1990–1999

| | | January | February | March | April | May | June | July | August | September | October | November | December |
| 1990 | Interview | Tom Cruise | Eddie Murphy | Donald Trump | Stephen Hawking | Dave Barry | Cast of thirtysomething | Quincy Jones | Larry King | Rickey Henderson | Shintaro Ishihara | Leona Helmsley | Jay Leno |
| 1990 | 20Q | Andrew Dice Clay | Dwight Yoakam | Dennis Hopper | John Larroquette | Jennifer Tilly | Willy T. Ribbs | Matt Groening | Dana Carvey | Maury Povich | Kiefer Sutherland | Chuck D | Elizabeth Perkins |
| 1991 | Interview | Lee Iacocca | Gene Siskel, Roger Ebert | M. Scott Peck | Martin Scorsese | George Steinbrenner | Robert MacNeil and Jim Lehrer | Spike Lee | Daryl Gates | Douglas Wilder | Robert Maxwell | Sean Penn | Carl Sagan |
| 1991 | 20Q | (none) | Lena Olin | (none) | George Foreman | Whitney Houston | John Milius | Eric Bogosian | Robert Downey Jr. | Danny Glover | Camille Paglia | Julia Roberts | Joe Pesci |
| 1992 | Interview | Robin Williams | Liz Smith | Lorne Michaels | Jonathan Kozol | Michael Jordan | Ralph Nader | Michael Keaton | Derek Humphry | Betty Friedan | Sister Souljah | William Safire | Sharon Stone |
| 1992 | 20Q | Woody Harrelson | Jennifer Jason Leigh | Forest Whitaker | Bobcat Goldthwait | John Leguizamo | Patrick Swayze | Nicole Kidman | Catherine Crier | Dennis Miller | Tim Robbins | Patrick Stewart | Helmut Newton |
| 1993 | Interview | Steve Martin | Danny DeVito | Anne Rice | Frank Zappa | Charles Barkley | Roseanne & Tom Arnold | Barry Bonds | Dan Aykroyd | Larry Kramer | Jerry Seinfeld | Joyce Carol Oates | Rush Limbaugh |
| 1993 | 20Q | Sean Young | Tim Allen | Laura Dern | Cindy Crawford | Giorgio Armani | Rebecca De Mornay | Rip Torn | Scott Turow | Sarah Jessica Parker | Wesley Snipes | Brian Dennehy | Branford Marsalis |
| 1994 | Interview | David Letterman | Pete Townshend | Anthony Hopkins | Howard Stern | Ron Howard | Garth Brooks | Bill Gates | Deion Sanders | David Geffen | Jerry Jones | Christian Slater | Garry Shandling |
| 1994 | 20Q | Shaquille O'Neal | Chris Berman | Halle Berry | Laurence Fishburne | Denis Leary | Fred Ward | Michael Moriarty | Dana Delany | David Caruso | Heather Locklear | Quentin Tarantino | Kelsey Grammer |
| 1995 | Interview | Jean-Claude Van Damme | Tim Robbins | Vladimir Zhirinovsky | David Mamet | Camille Paglia | Joycelyn Elders | Mel Gibson | Berry Gordy | Cindy Crawford | Snoop Dogg | Harvey Keitel | George Foreman |
| 1995 | 20Q | Tom Snyder | David Spade | Jon Stewart | Samuel L. Jackson | David Hasselhoff | Tom Arnold | Kurt Loder | Dawn Steel | Sandra Bullock | Bill Maher | G. Gordon Liddy | Dominick Dunne |
| 1996 | Interview | Johnny Depp | Bruce Willis | John Travolta | Salman Rushdie | Ray Bradbury | Dennis Miller | James Carville | Shaquille O'Neal | Nicolas Cage | Jay Leno | Liam Neeson | Mike Wallace |
| 1996 | 20Q | Robin Quivers | Harry Wu | Dick Vitale | Michael Madsen | Lou Dobbs | Julia Louis-Dreyfus | Chazz Palminteri | Heidi Fleiss | Janeane Garofalo | Jimmy Smits | Chris O'Donnell | Lisa Kudrow |
| 1997 | Interview | Whoopi Goldberg | Lawrence Schiller | Clint Eastwood | Vincent Bugliosi | Saul Bellow | Dennis Rodman | Anthony Edwards | Bill Maher | Christopher Walken | Tommy Hilfiger | Brett Favre | Robert Downey Jr. |
| 1997 | 20Q | Mike Judge | Conan O'Brien | Michael Jordan | Vanessa Williams | Lucy Lawless | Julianna Margulies | Jon Lovitz | Norm Macdonald | Chris Farley | Téa Leoni | Robert Wuhl | Chris Rock |
| 1998 | Interview | Grant Hill | Conan O'Brien | Kevin Kline | Joe Eszterhas | Scott Adams | Paul Reiser | Jerry Springer | Matt Drudge | Daniel Patrick Moynahan | Geraldo Rivera | Mike Tyson | David Duchovny |
| 1998 | 20Q | Teri Hatcher | Paul Thomas Anderson | John Peterman | Keith Olbermann | Ben Stiller | Yasir Arafat | Craig Kilborn | Bruce Willis | Kevin Williamson | Tori Spelling | Drew Pinsky | Gore Vidal |
| 1999 | Interview | Michael Crichton | Emeril Lagasse | Drew Carey | Nick Nolte | David Spade | Samuel L. Jackson | Barney Frank | Albert Brooks | Chris Rock | Kevin Spacey | Jesse Ventura | Ben Affleck |
| 1999 | 20Q | Kirstie Alley | The Motley Fool | Gerry Adams | David Schwimmer | Ashley Judd | Christina Applegate | Michael Moore | Lucy Liu | Jeri Ryan | Joe Morgan | George Jones | Gina Gershon |

## 2000–2009

| | | January | February | March | April | May | June | July | August | September | October | November | December |
| 2000 | Interview | Hugh Hefner | Jeff Bezos | Jon Stewart | Rowland Evans, Robert Novak | Pete Rose | Trey Parker, Matt Stone | George Clooney | John Malkovich | Jennifer Lopez | Bob Costas | Ben Stiller | Drew Barrymore |
| 2000 | 20Q | Rupert Everett | Steven Van Zandt | Cindy Margolis | Barry White | Michael Palin | James Coburn | Carson Daly | Aimee Mann | Seth Green | Michael Johnson | Neil LaBute | Jakob Dylan |
| 2001 | Interview | Gary Johnson | Vince McMahon | Bobby Knight | Metallica | Tom Green | Charlie Sheen | Chris Matthews | Tim Burton | Dale Earnhardt Jr. | Cast of The West Wing | The Coen Brothers | Will Smith |
| 2001 | 20Q | Carol Alt | Sela Ward | Traci Lords | Wyclef Jean | Mariska Hargitay | Edward Burns | Johnny Knoxville | Jon Bon Jovi | Stanley Tucci | Marg Helgenberger | Will Ferrell | Catherine Bell |
| 2002 | Interview | Brit Hume | Gary Hart | Allen Iverson | Lennox Lewis | Bill O'Reilly | Curt Schilling | Fred Durst | Harrison Ford | Larry Ellison | Al Michaels | Willie Nelson | Denzel Washington |
| 2002 | 20Q | Dan Patrick | Hugh Jackman | Jamie Foxx | Sarah Silverman | Milla Jovovich | Oscar de la Hoya | Chris Isaak | Amanda Peet | Lenny Kravitz | Jamie Oliver | Marshall Faulk | Greg Kinnear |
| 2003 | Interview | Halle Berry | Jimmy Kimmel | Colin Farrell | Jay-Z | Billy Bob Thornton | Mike Piazza | Lisa Marie Presley | Tobey Maguire | Jon Gruden | O.J.Simpson | Quentin Tarantino | John Cusack |
| 2003 | 20Q | Ron Insana | Bernie Mac | Juliette Lewis | Andy Richter | Jorja Fox | Nelly | Rachel Weisz | Charles Rangel | Nicolas Cage | Joe Rogan | Bill Murray | William H. Macy |
| 2004 | Interview | Jack Nicholson | Kiefer Sutherland | Jim Carrey | 50 Cent | Johnny Depp | Derek Jeter | Michael Moore | Matt Damon | Google Guys | Donald Trump | Oliver Stone | Bernie Mac |
| 2004 | 20Q | Al Franken | Dave Matthews | William Petersen | Kevin Smith | Matthew Perry | Jude Law | Christina Applegate | Spike Lee | Terrell Owens | Jimmy Fallon | John Carmack | Dustin Hoffman |
| 2005 | Interview | Toby Keith | Nicole Kidman | The Rock | Les Moonves | James Spader | Lance Armstrong | Owen Wilson | Ewan McGregor | Thomas L. Friedman | George Carlin | Jamie Foxx | Pierce Brosnan |
| 2005 | 20Q | James Caan | Jolene Blalock | Kid Rock | Mena Suvari | Vitali Klitschko | Paul Giamatti | Scarlett Johansson | Kate Hudson | Kurt Busch | Ozzy Osbourne | Steve Carell | Al Pacino |
| 2006 | Interview | Mark Cuban | Al Franken | Kanye West | Keanu Reeves | Ozzie Guillen | Shepard Smith | Jerry Bruckheimer | Denis Leary | Michael Brown | Ludacris | Arianna Huffington | Dixie Chicks |
| 2006 | 20Q | Kate Beckinsale | Hugh Laurie | Franz Ferdinand | Craig Ferguson | Rebecca Romijn | Jason Lee | Dana White | Luke Wilson | Eva Longoria | Johnny Knoxville | Tenacious D | Samuel L. Jackson |
| 2007 | Interview | T. Boone Pickens | Simon Cowell | Jeremy Piven | Bill Maher | Steve Nash | Matt Groening | Bruce Willis | Chris Tucker | Clive Owen | Keith Olbermann | Robert Redford | Bill Richardson |
| 2007 | 20Q | Ellen Pompeo | Bettie Page | Mariah Carey | Will Arnett | Fergie | Don Rickles | Danica Patrick | Paul Rudd | Jamie Pressly | Ali Larter | Matt Leinart | Joaquin Phoenix |
| 2008 | Interview | Tina Fey | Matthew McConaughey | Garry Kasparov | Chad Kroeger | Fareed Zakaria | Steve Carell | Drew Pinsky | Ben Stiller | Dana White | Pete Wentz | Daniel Craig | Hugh Jackman |
| 2008 | 20Q | Helena Bonham Carter | Rachel Bilson | Charles Barkley | Jenna Fischer | Bob Saget | Harvey Levin | Lewis Black | Selma Blair | Anna Faris | Kevin Connolly | Chelsea Handler | Rosario Dawson |
| 2009 | Interview | Richard Branson | Hugh Laurie | Kenny Chesney | Seth Rogen | Chuck Palahniuk | Shia Labeouf | Alec Baldwin | Alec Baldwin | Seth MacFarlane | Woody Harrelson | Benicio Del Toro | James Cameron |
| 2009 | 20Q | Marston and Cooper Hefner | Josh Holloway | Flight Of The Concords | Amy Smart | Zachary Quinto | Scott Boras | Judd Apatow | Judd Apatow | Diane Kruger | Shawne Merriman | Tracy Morgan | Quinton Jackson |

## 2010–2020 / 2025

| | | January | February | March | April | May | June | July | August | September | October | November | December |
| 2010 | Interview | Sean Combs | Sean Combs | John Mayer | Sarah Silverman | Matthew Fox | Michael Savage | Cameron Diaz | Cornel West | Paul Reubens | Josh Brolin | Robert Downey Jr. | Conan O'Brien |
| 2010 | 20Q | Guy Fieri | Guy Fieri | Shaun White | Will Forte | B. J. Novak | Russell Brand | Stephen Moyer | Michael Cera | John Varvatos | William Shatner | Zach Galifianakis | Olivia Wilde |
| 2011 | Interview | Frank Gehry | Lamar Odom | Deepak Chopra | Helen Thomas | Barney Frank | Lawrence O'Donnell | Justin Timberlake | James Franco | Steve Buscemi | Paul Rudd | Anthony Bourdain | Craig Ferguson |
| 2011 | 20Q | Chloë Sevigny | Aziz Ansari | Seth Green | Josh Radnor | Ed Helms | Louis C.K. | Jason Sudeikis | Bryan Cranston | Amber Heard | Gordon Ramsay | Rashida Jones | Kaley Cuoco |
| 2012 | Interview | Chris Wallace | Chris Wallace | Paul Krugman | Jon Hamm | David Brooks | Tom Cruise | Charlie Sheen | Charlie Sheen | Richard Dawkins | Lee Child | Stephen Colbert | Quentin Tarantino |
| 2012 | 20Q | Nick Offerman | Nick Offerman | David Cross | Meghan McCain | Chris Evans | Rhys Ifans | Andy Samberg | Andy Samberg | Joseph Gordon-Levitt | Dax Shepard | Krysten Ritter | Padma Lakshmi |
| 2013 | Interview | Matt Damon | Matt Damon | Jimmy Kimmel | Clive Davis | J. J. Abrams | Ai Weiwei | Sean Hannity | Sean Hannity | Tony Robbins | Samuel L. Jackson | Bernie Sanders | Ray Kelly |
| 2013 | 20Q | Scott Speedman | Scott Speedman | Chris Hardwick | Lena Dunham | Peter Dinklage | Kevin Smith and Jason Mewes | Armie Hammer | Armie Hammer | Bill Hader | James Deen | Idris Elba | James Marsden |
| 2014 | Interview | Ben Affleck | Ben Affleck | Nick Denton | Stan Lee | Tony Hsieh | Jonah Hill | Gary Oldman | Gary Oldman | James Spader | David Fincher | Brian Schweitzer | Joaquin Phoenix |
| 2014 | 20Q | Patton Oswalt | Patton Oswalt | Ty Burrell | Iggy Pop | Kate Mara | Kevin Hart | Marc Maron | Marc Maron | Frank Miller | Bob Corddry | David Walton | Charlie Day |
| 2015 | Interview | Joaquin Phoenix | Joaquin Phoenix | Vince Vaughn | Dick Cheney, Azealia Banks | Bill Maher | Reza Aslan | Jeremy Renner | Jeremy Renner | Sanjay Gupta | Joseph Gordon-Levitt | Christoph Waltz | Bryan Cranston |
| 2015 | 20Q | Nick Kroll | Nick Kroll | Ben Schwartz | Aubrey Plaza | Josh Hartnett | | | | | | | |
| 2016 | Interview | Ron Howard | Ron Howard | Rachel Maddow | Don Cheadle | Ray Kurzweil | Trevor Noah | Ta-Nehisi Coates | Ta-Nehisi Coates | Andy Samberg | Jason Dill | Michael Hayden | Billy Bob Thornton |
| 2016 | 20Q | | | | | | | | | | | | |
| 2017 | Interview | Matthew McConaughey | Matthew McConaughey | Scarlett Johansson | Scarlett Johansson | Ezra Klein | Ezra Klein | Christopher Nolan | Christopher Nolan | Patton Oswalt | Patton Oswalt | Chelsea Handler | Chelsea Handler |
| 2017 | 20Q | | | | | | | | | | | | |
| 2018 | Interview | Christie Hefner | Christie Hefner | John Krasinski | John Krasinski | Cecile Richards | Cecile Richards | Kathy Griffin | Kathy Griffin | Michael Shannon | Michael Shannon | Tucker Carlson | Tucker Carlson |
| 2018 | 20Q | Cillian Murphy | Cillian Murphy | Jesse Plemons | Jesse Plemons | Jim Jefferies | Jim Jefferies | Lakeith Stanfield | Lakeith Stanfield | Sofia Boutella | Sofia Boutella | Charlie Cox | Charlie Cox |
| 2019 | Interview | Sam Harris | Sam Harris | Sam Harris | Seth Ambramson | Seth Ambramson | Seth Ambramson | Tarana Burke | Tarana Burke | Tarana Burke | Jeremy O. Harris | Jeremy O. Harris | Jeremy O. Harris |
| 2019 | 20Q | | | | | | | | | | | | |
| 2020 | Interview | Christiane Amanpour | Christiane Amanpour | Christiane Amanpour | Jameela Jamil | Jameela Jamil | Jameela Jamil | -- | -- | -- | -- | -- | -- |
| 2020 | 20Q | | | | | | | | | | | | |
| 2025 | Interview | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser | Nikki Glaser |
| 2025 | 20Q | | | | | | | | | | | | |