| Year | Actor | Role | Work | Nominees | Ref. |
| 1949 | | | | — | |
| 1950 | — | — | — | — | |
| 1951 | | | | — | |
| 1952 | | | | — | |
| 1953 | | | | — | |
| 1954 | | | | — | |
| 1955 | | | | — | |
| 1956 | | | |
- Anthony Franciosa in A Hatful of Rain as Polo Pope
- Andy Griffith in No Time for Sergeants as Will Stockdale
- Anthony Quayle in Tamburlaine the Great as Tamburlaine
- Fritz Weaver in The Chalk Garden as Maitland
| |
| 1957 | | | | Eddie Mayehoff in A Visit to a Small Planet as General Tom Powers William Podmore in Separate Tables as Mr. FowlerJason Robards in Long Day's Journey into Night as James Tyrone, Jr. | |
| 1958 | | | | Sig Arno in Time Remembered as FerdinandTheodore Bikel in The Rope Dancers as Dr. JacobsonPat Hingle in The Dark at the Top of the Stairs as Rubin FloodGeorge Relph in The Entertainer as Billy Rice | |
| 1959 | | | | Marc Connelly in Tall Story as Professor Charles OsmanGeorge Grizzard in The Disenchanted as Shep StearnsWalter Matthau in Once More, with Feeling as Maxwell ArcherRobert Morse in Say, Darling as Ted SnowGeorge C. Scott in Comes a Day as Tydings Glenn | |
| 1960 | | | | Warren Beatty in A Loss of Roses as KennyHarry Guardino in One More River as PompeyRip Torn in Sweet Bird of Youth as Tom JuniorLawrence Winters in The Long Dream as Tyree Tucker | |
| 1961 | | | | Philip Bosco in The Rape of the Belt as HeraclesEduardo Ciannelli in The Devil's Advocate as AurelioGeorge Grizzard in Big Fish, Little Fish as Ronnie Johnson | |
| 1962 | | | | Godfrey Cambridge in Purlie Victorious as Gitlow JudsonJoseph Campanella in A Gift of Time as Daniel SteinPaul Sparer in Ross as Auda Abu Tayi | |
| 1963 | | | | Barry Gordon in A Thousand Clowns as Nick BurnsPaul Rogers in Photo Finish as Reginald Kinsale, Esq.Frank Silvera in The Lady of the Carnellias as M. Duval | |
| 1964 | | | | Lee Allen in Marathon '33 as PatsyMichael Dunn in The Ballad of the Sad Café as Cousin LymanLarry Gates in A Case of Libel as Boyd Bendix | |
| 1965 | | | | Murray Hamilton in Absence of a Cello as Otis CliftonMartin Sheen in The Subject Was Roses as Timmy ClearyClarence Williams III in Slow Dance on the Killing Ground as Randall | |
| 1966 | | | | Burt Brinckerhoff in Cactus Flower as IgorLarry Haines in Generation as Stan HermanEamon Kelly in Philadelphia, Here I Come! as S. B. O'Donnell | |
| 1967 | | | | Clayton Corzatte in The School for Scandal as Charles SurfaceStephen Elliott in Marat/Sade as Mr. CoulmierSydney Walker in The Wild Duck as Lt. Ekdal | |
| 1968 | | | | Paul Hecht in Rosencrantz and Guildenstern Are Dead as The PlayerBrian Murray in Rosencrantz and Guildenstern Are Dead as RosencrantzJohn Wood in Rosencrantz and Guildenstern Are Dead as Guildenstern | |
| 1969 | | | | Richard S. Castellano in Lovers and Other Strangers as FrankTony Roberts in Play It Again, Sam as Dick ChristieLouis Zorich in Hadrian VII as Cardinal Ragna | |
| 1970 | | | | Joseph Bova in The Chinese and Dr. Fish as Mr. LeeDennis King in A Patriot for Me as Baron von Epp | |
| 1971 | | | | Ronald Radd in Abelard and Heloise as Gilies de VannesDonald Pickering in Conduct Unbecoming as Capt. Rupert HarperEd Zimmermann in The Philanthropist as Donald | |
| 1972 | | | | Douglas Rain in Vivat! Vivat Regina! as William CecilLee Richardson in Vivat! Vivat! Regina! as Lord BothwellJoe Silver in Lenny as Various Characters | |
| 1973 | | | | Barnard Hughes in Much Ado About Nothing as DogberryJohn McMartin in Don Juan as SganarelleHayward Morse in Butley as Joseph Keyston | |
| 1974 | | | | René Auberjonois in The Good Doctor as PerformerDouglas Turner Ward in The River Niger as Johnny WilliamsDick Anthony Williams in What the Wine-Sellers Buy as Rico | |
| 1975 | | | | Larry Blyden in Absurd Person Singular as SidneyLeonard Frey in The National Health as BarnetPhilip Locke in Sherlock Holmes as Professor MoriartyGeorge Rose in My Fat Friend as HenryDick Anthony Williams in Black Picture Show as Alexander | |
| 1976 | | | | Barry Bostwick in They Knew What They Wanted as JoeGabriel Dell in Lamppost Reunion as Fred SantoraDaniel Seltzer in Knock Knock as Cohn | |
| 1977 | | | | Bob Dishy in Sly Fox as Abner TruckleJoe Fields in The Basic Training of Pavlo Hummel as First Sergeant TowerLaurence Luckinbill in The Shadow Box as Brian | |
| 1978 | | | | Morgan Freeman in The Mighty Gents as ZekeVictor Garber in Deathtrap as Clifford AndersonCliff Gorman in Chapter Two as Leo Schneider | |
| 1979 | | | | Bob Balaban in The Inspector General as ÓssipJoseph Maher in Spokesong as The Trick CyclistEdward James Olmos in Zoot Suit as El Pachuco | |
| 1980 | | | | David Dukes in Bent as HorstGeorge Hearn in Watch on the Rhine as Kurt MullerEarle Hyman in The Lady from Dubuque as OscarJoseph Maher in Night and Day as Geoffrey Carson | |
| 1981 | | | | Tom Aldredge in The Little Foxes as Horace GiddensAdam Redfield in A Life as DesmondShepperd Strudwick in To Grandmother's House We Go as Jared | |
| 1982 | | | | Richard Kavanaugh in The Hothouse as GibbsEdward Petherbridge in The Life and Adventures of Nicholas Nickleby as Newman NoggsDavid Threlfall in The Life and Adventures of Nicholas Nickleby as Smike | |
| 1983 | | | | Željko Ivanek in Brighton Beach Memoirs as Stanley JeromeGeorge N. Martin in Plenty as Leonard DarwinStephen Moore in All's Well That Ends Well as Captain Parolles | |
| 1984 | | | | Philip Bosco in Heartbreak House as Boss ManganRobert Prosky in Glengarry Glen Ross as Shelly LeveneDouglas Seale in Noises Off as Selsdon Mowbray | |
| 1985 | | | | Charles S. Dutton in Ma Rainey's Black Bottom as LeveeWilliam Hurt in Hurlyburly as EddieEdward Petherbridge in Strange Interlude as Charles Marsden | |
| 1986 | | | | Peter Gallagher in Long Day's Journey into Night as Edmund TyroneCharles Keating in Loot as McLeavyJoseph Maher in Loot as Truscott | |
| 1987 | | | | Frankie R. Faison in Fences as GabrielJamey Sheridan in All My Sons as Chris KellerCourtney B. Vance in Fences as Corey | |
| 1988 | | | | Michael Gough in Breaking the Code as Dillwyn KnoxLou Liberatore in Burn This as LarryDelroy Lindo in Joe Turner's Come and Gone as Herald Loomis | |
| 1989 | | | | Peter Frechette in Eastern Standard as DrewEric Stoltz in Our Town as George GibbsGordon Joseph Weiss in Ghetto as The Dummy | |
| 1990 | | | | Rocky Carroll in The Piano Lesson as LymonTerry Kinney in The Grapes of Wrath as Jim CasyGary Sinise in The Grapes of Wrath as Tom Joad | |
| 1991 | | | | Adam Arkin in I Hate Hamlet as Gary Peter LefkowitzDylan Baker in La Bête as Prince CountyStephen Lang in The Speed of Darkness as Lou | |
| 1992 | | | | Roscoe Lee Browne in Two Trains Running as HollowayŽeljko Ivanek in Two Shakespearean Actors as John RyderTony Shalhoub in Conversations with My Father as Charlie | |
| 1993 | | | | Robert Sean Leonard in Candida as Eugene MarchbanksJoe Mantello in Angels in America: Millennium Approaches as Louis IronsonZakes Mokae in The Song of Jacob Zulu as Rev. Zulu/Mr. X, Itshe | |
| 1994 | | | | Larry Bryggman in Picnic as Howard BevansDavid Marshall Grant in Angels in America: Perestroika as Joe Pitt/Various CharactersGregory Itzin in The Kentucky Cycle as Various Characters | — |
| 1995 | | | | Stephen Bogardus in Love! Valour! Compassion! as Gregory MitchellAnthony Heald in Love! Valour! Compassion! as Perry SellarsJude Law in Indiscretions as Michael | |
| 1996 | | | | James Gammon in Buried Child as DodgeRoger Robinson in Seven Guitars as HedleyReg Rogers in Holiday as Ned Seton | |
| 1997 | | | | Terry Beaver in The Last Night of Ballyhoo as AdolphBrian Murray in The Little Foxes as OscarBiff McGuire in The Young Man From Atlanta as Pete Davenport | |
| 1998 | | | | Brían F. O'Byrne in The Beauty Queen of Leenane as Pato DooleySam Trammell in Ah, Wilderness! as Richard MillerMax Wright in Ivanov as Pavel Lebedev | |
| 1999 | | | | Kevin Anderson in Death of a Salesman as BiffFinbar Lynch in Not About Nightingales as Jim AllisonHoward Witt in Death of a Salesman as Charley | |
| 2000 | | | | Kevin Chamberlin in Dirty Blonde as Various CharactersDaniel Davis in Wrong Mountain as Maurice MontesorDerek Smith in The Green Bird as TartagliaBob Stillman in Dirty Blonde as Various Characters | |
| 2001 | | , from ages 18 to 26 | | Charles Brown in King Hedley II as ElmoreLarry Bryggman in Proof as RobertMichael Hayden in Judgment at Nuremberg as Oscar RolfeBen Shenkman in Proof as Hal | |
| 2002 | | | | Brian Murray in The Crucible as Deputy-Governor DanforthWilliam Biff McGuire in Morning's at Seven as Theodore SwansonSam Robards in The Man Who Had All the Luck as Gustav EbersonStephen Tobolowsky in Morning's at Seven as Homer Bolton | |
| 2003 | | | | Thomas Jefferson Byrd in Ma Rainey's Black Bottom as ToledoPhilip Seymour Hoffman in Long Day's Journey into Night as JamieRobert Sean Leonard in Long Day's Journey into Night as EdmundDaniel Sunjata in Take Me Out as Darren Lemming | |
| 2004 | | | | Tom Aldredge in Twentieth Century as Matthew ClarkBen Chaplin in The Retreat from Moscow as JamieAidan Gillen in The Caretaker as MickOmar Metwally in Sixteen Wounded as Mahmoud | |
| 2005 | | | | Alan Alda in Glengarry Glen Ross as LevineGordon Clapp in Glengarry Glen Ross as MossDavid Harbour in Edward Albee's Who's Afraid of Virginia Woolf? as NickMichael Stuhlbarg in The Pillowman as Michal | |
| 2006 | | | | Samuel Barnett in The History Boys as PosnerDomhnall Gleeson in The Lieutenant of Inishmore as DaveyMark Ruffalo in Awake and Sing! as Moe AxelrodPablo Schreiber in Awake and Sing! as Ralph Berger | |
| 2007 | | | | Anthony Chisholm in Radio Golf as Elder Joseph BarlowEthan Hawke in The Coast of Utopia as Michael BakuninJohn Earl Jelks in Radio Golf as Sterling JohnsonStark Sands in Journey's End as Lieut. Raleigh | |
| 2008 | | | | Bobby Cannavale in Mauritius as DennisRaúl Esparza in The Homecoming as LennyConleth Hill in The Seafarer as Ivan CurryDavid Pittu in Is He Dead? as Various Characters | |
| 2009 | | | | John Glover in Waiting for Godot as LuckyZach Grenier in 33 Variations as BeethovenStephen Mangan in The Norman Conquests as NormanPaul Ritter in The Norman Conquests as Reg | |
| 2010 | | | | David Alan Grier in Race as Henry BrownStephen Henderson in Fences as Jim BonoJon Michael Hill in Superior Donuts as FrancoStephen Kunken in ENRON as Andy Fastow | |
| 2011 | | | | Mackenzie Crook in Jerusalem as GingerBilly Crudup in Arcadia as Bernard NightingaleArian Moayed in Bengal Tiger at the Baghdad Zoo as MusaYul Vázquez in The Motherfucker With the Hat as Cousin Julio | |
| 2012 | | | | Michael Cumpsty in End of the Rainbow as AnthonyTom Edden in One Man, Two Guvnors as AlfieAndrew Garfield in Arthur Miller’s Death of a Salesman as Biff LomanJeremy Shamos in Clybourne Park as Karl/Steve | |
| 2013 | | | | Danny Burstein in Golden Boy as TokioRichard Kind in The Big Knife as Marcus HoffBilly Magnussen in Vanya and Sonia and Masha and Spike as SpikeTony Shalhoub in Golden Boy as Mr. Bonaparte | |
| 2014 | | | | Reed Birney in Casa Valentina as CharlottePaul Chahidi in Twelfth Night as MariaStephen Fry in Twelfth Night as MalvolioBrian J. Smith in The Glass Menagerie as Jim O'Connor | |
| 2015 | | | | Matthew Beard in Skylight as Edward Sergeant K. Todd Freeman in Airline Highway as Sissy Na Na Alessandro Nivola in The Elephant Man as Frederick Treves Nathaniel Parker in Wolf Hall Parts One & Two as Henry VIII Micah Stock in It's Only a Play as Gus P. Head | |
| 2016 | | | | Bill Camp in The Crucible as Reverend John Hale David Furr in Noises Off as Gary Lejeune Richard Goulding in King Charles III as Prince Harry Michael Shannon in Long Day's Journey into Night as James Tyrone, Jr. | |
| 2017 | | | | Danny DeVito in The Price as Gregory Solomon Nathan Lane in The Front Page as Walter Burns Richard Thomas in The Little Foxes as Horace Giddens John Douglas Thompson in Jitney as Jim Becker | |
| 2018 | | | | Anthony Boyle in Harry Potter and the Cursed Child as Scorpius Malfoy Michael Cera in Lobby Hero as Jeff Brian Tyree Henry in Lobby Hero as William David Morse in The Iceman Cometh as Larry Slade | |
| 2019 | | | | Robin de Jesús in The Boys in the Band as Emory Gideon Glick in To Kill a Mockingbird as Dill Harris Brandon Uranowitz in Burn This as Larry Benjamin Walker in All My Sons as Chris Keller | |
