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 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 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 generated controversy due to her forthright critique 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

JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember1962Interview"Playboy Interview" begins September 1962:Miles Davis(none)(none)Jackie Gleason1963Interview(none)Frank SinatraBertrand RussellHelen Gurley BrownMalcolm XBilly Wilder(none)(none)Richard BurtonJames HoffaAlbert Schweitzer1964InterviewVladimir Nabokov(none)Ayn RandJean Genet(none)Ingmar BergmanSalvador DalíDick GregoryHenry MillerCassius ClayGeorge WallaceIan Fleming1965InterviewMartin Luther KingThe Beatles(none)Art BuchwaldJean-Paul SartreMelvin BelliMarcello MastroianniRobert SheltonPeter O'TooleMadalyn MurraySean ConneryAl Capp1966InterviewPrincess GraceFederico FelliniBob DylanGeorge Lincoln RockwellArthur Schlesinger, Jr.Mike NicholsRalph GinzburgH. L. HuntTimothy LearyMel BrooksNorman ThomasSammy Davis Jr.1967InterviewFidel CastroMark LaneOrson WellesArnold ToynbeeWoody Allen(none)Michael CaineF. Lee BaileyJohn V. LindsayJim GarrisonMichelangelo AntonioniJohnny Carson1968InterviewNorman MailerJim BrownTruman CapoteCharles PercyMasters and JohnsonJohn Kenneth GalbraithPaul Newman(none)Stanley KubrickRalph NaderDon Rickles(none)1969InterviewMartin Luther King Jr.Mort SahlMarshall McLuhanAllen GinsbergBill CosbyGore VidalRod SteigerRamsey Clark(none)Rowan and MartinJesse JacksonJoe Namath

1970–1979

JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember1970InterviewRaquel Welch (none)Ray CharlesMary CalderoneWilliam F. Buckley Jr.Tiny TimJoan BaezPaul R. EhrlichPeter FondaWilliam KunstlerElliott GouldRobert Graves1971Interview (none)Tom MurtonDick Cavett(none)John WayneAlbert SpeerJohn CassavetesGeorge McGovernJules FeifferCharles EversAllen KleinRoman Polanski1972InterviewGermaine GreerR. Buckminster FullerSaul AlinskyJack NicholsonHoward CosellJackie StewartAnthony HerbertSam PeckinpahBernadette DevlinMeir KahaneJack AndersonYevgeny Yevtushenko1973InterviewCarroll O'ConnorMilton FriedmanJoe FrazierTennessee WilliamsHuey NewtonWalter CronkiteKurt Vonnegut Jr.David Halberstam(none)Pete RozelleJames DickeyBob Hope1974InterviewHugh HefnerClint EastwoodGroucho MarxJane Fonda, Tom HaydenHenry AaronElmo ZumwaltBarry CommonerErich von DänikenAnthony BurgessAl GoldsteinHunter ThompsonRobert Redford1975InterviewJohn DeanMel BrooksBillie Jean KingDustin HoffmanWilliam E. SimonJoseph HellerFrancis Ford CoppolaPhilip AgeeErica JongCherMuhammad AliJimmy Hoffa1976InterviewElton JohnJames CaanNorman LearJerry BrownAbbie HoffmanSara Jane MooreKarl HessRobert AltmanDavid BowieRoone ArledgeJimmy CarterO. J. Simpson1977InterviewAlex HaleyKeith StroupPat MoynihanGary GilmoreCast of Saturday Night LiveRobert BlakeAndrew YoungHenry WinklerJames Earl RayBarbra StreisandHenry KyembaJohn Denver1978InterviewPlayboy Panel: UFOsDon MeredithBob DylanDavid FrostAnita BryantGeorge BurnsWilliam ColbyTed TurnerSylvester StalloneDolly PartonGeraldo RiveraJohn Travolta20Q"20Q" begins October 1978:Cheryl Tiegs(none)(none)1979InterviewMarlon BrandoNeil SimonTed PatrickMalcolm ForbesWendy CarlosDennis KucinichJoseph WambaughEdward TellerPete RoseBurt ReynoldsMasters and JohnsonAl Pacino20Q(none)(none)(none)(none)Dan Rather(none)(none)Frank Langella(none)(none)(none)(none)

1980–1989 JanuaryFebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecember1980InterviewSteve MartinPatrick CaddellTerry BradshawLinda RondstatGay TaleseJohn AndersonBruce JennerWilliam ShockleyRoy ScheiderG. Gordon LiddyLarry HagmanGeorge C. Scott20Q (none) (none)Shelley Hack (none) (none) (none)George Hamilton (none) (none) (none)Michael DouglasTruman Capote1981InterviewJohn Lennon / Yoko OnoTom SnyderJames GarnerEd AsnerElisabeth Kubler-RossSteve GarveyRobert GarwoodGeorge GilderJames MichenerDonald SutherlandOriana FallaciHenry Fonda20Q (none) (none)Lauren Hutton (none)John DeLoreanJack Lemmon (none)Joan Rivers (none) (none) (none)John Kenneth Galbraith1982InterviewGeorge CarlinLech WalesaPatricia HearstEdward KochBilly JoelSugar Ray LeonardBette DavisAkio MoritaCheech and ChongRobin WilliamsLuciano PavorottiJulie Andrews, Blake Edwards20QJohn MatuszakKaren AllenLouis RukeyserJames WoodsSCTVBrandon TartikoffStevie NicksMariette HartleyTom PettyJohn Le BoutillierFrank and Moon Unit Zappa(none)1983InterviewDudley MooreGabriel García MárquezSam DonaldsonPaul NewmanAnsel AdamsStephen KingEarl WeaverTed TurnerThe Sandinistas, Daniel OrtegaCast of Hill Street BluesKenny RogersTom Selleck20QHerschel WalkerYakov SmirnoffArthur JonesAl McGuireCharlton HestonDebra WingerCarrie FisherJan StephensonRandy NewmanJoe PiscopoBubba Smith(none)1984InterviewDan RatherPaul SimonMoses MaloneJoan CollinsCalvin KleinJesse JacksonWalid JumblattBobby KnightShirley MacLaineDavid LettermanJosé Napoleón DuartePaul and Linda McCartney20Q(none)Shelley Long(none)Martin Mull(none)Siskel and EbertFran LebowitzKurt Russell(none)Jack LaLanneLeigh Steinberg(none)1985InterviewGoldie HawnSteve JobsCast of 60 MinutesWayne GretzkyBoy GeorgeSparky AndersonRob ReinerFidel CastroJohn HustonJohn DeLoreanStingBill Cosby20QDiane LaneBrian De PalmaBob GiraldiJoel HyattMarvin Hagler, Thomas HearnsTom WatsonJamie Lee CurtisRon HowardBilly CrystalRosanna ArquetteDon Johnson, Philip Michael ThomasHuey Lewis1986InterviewRuth WestheimerMichael DouglasSally FieldJeffrey MacDonaldKathleen TurnerKareem Abdul-JabbarArthur C. ClarkeJackie GleasonCarl BernsteinPhil CollinsJoan RiversBryant Gumbel20QJay LenoAnthony PellicanoDavid Byrne(none)Kim BasingerAl Unser, Sr., Al Unser, Jr.Tom CruiseSigourney WeaverGregory HinesJim McMahonDavid HorowitzKoko1987InterviewDon JohnsonMickey RourkeLionel RichieLouis RukeyserPrince Norodom SihanoukWhoopi GoldbergWade BoggsImelda and Ferdinand MarcosJohn SculleyGeneral Richard SecordDaniel OrtegaGore Vidal20QMax HeadroomEd Begley Jr.Bob VilaRae Dawn ChongBarbara HersheyMichael J. FoxGarry ShandlingDavid Lee RothPenn And TellerBob UeckerKelly McGillisJustine Bateman1988InterviewArnold SchwarzeneggerOliver StoneBilly CrystalTom ClancyDon KingChevy ChasePaul HoganHarvey FiersteinYasser ArafatRoger CraigBruce WillisCher20QSusan DeyHarold WashingtonTom WaitsHarrison FordTeri GarrTheresa RussellJudge ReinholdHarry EdwardsTracey UllmanMorton Downey Jr.John CleeseGene Simmons1989InterviewRobert De NiroBob WoodwardTom HanksThe I.R.A.Susan SarandonEdward James OlmosBarry DillerJohn Cougar MellencampKeith HernandezKeith RichardsGarry KasparovCandice Bergen20Q(none)Andrea MarcovicciFred DryerMario LemieuxRichard LewisNicolas CageWilliam ShatnerJohn CandyJeff DanielsGeena DavisBonnie RaittPatti D'Arbanville

1990–1999