Past Recipients: 1945-Present
| Year | Recipient | Role | Play |
| 2023 | Alex Newell | Lulu | Shucked |
| Bonnie Milligan | Debra | Kimberly Akimbo | |
| 2022 | Kara Young | ||
| Justin Cooley | |||
| 2019 | Sarah Stiles | Sandy | Tootsie |
| Ephraim Sykes | David Ruffin | Ain't too Proud | |
| 2018 | Ashley Park | K Pop And Mean Girls | |
| Sean Carvajal | Jesus Hopped The A Train | ||
| 2017 | Katrina Lenk | Bands Visit | |
| Will Pullen | Sweat | ||
| 2016 | Alana Arenas | Cookie | Head Of Passes |
| Ben Platt | Evan | Dear Evan Hansen | |
| 2015 | Phillipa Soo | Eliza Hamilton | Hamilton |
| Josh Grisetti | Marty | It Shoulda Been You | |
| 2014 | Whitney Bashor | The Bridges Of Madison County | |
| Steven Boyer | Hand To God | ||
| 2013 | Annaleigh Ashford | Kinky Boots | |
| Michael Urie | Buyer & Seller | ||
| 2012 | Susan Pourfar | In The Wake | |
| Finn Wittrock | Death Of A Salesman | ||
| 2011 | Tracee Chimo | Bachelorette | |
| Santino Fontana | The Importance Of Being Earnest | ||
| 2010 | Nina Arianda | Vanda | Venus In Fur |
| Bill Heck | Multiple Roles | The Orphans' Home Cycle | |
| 2009 | Quincy Tyler Bernstine | Ruined | |
| Aaron Tveit | Gabe | Next To Normal | |
| 2008 | Zoe Kazan | Come Back, Little Sheba; Things We Want; 100 Saints You Should Know | |
| Michael Esper | Crazy Mary | ||
| 2007 | Leslie Kritzer | Serena | Legally Blonde |
| Lin-Manual Miranda | Usnavi | In The Heights | |
| 2006 | Felicia P. Fields | Sofia | The Color Purple |
| Jason Ritter | Woodson Bull, III | Third | |
| 2005 | Ari Graynor | Alison | Brooklyn Boy |
| Christian Borle | Historian, Not Dead Fred, French Guard, Minstrel and Prince Herbert | Monty Python Spamalot | |
| 2004 | Anika Noni Rose | Emmie Thibodeaux | Caroline, Or Change |
| John Tartaglia | Princeton and Rod | Avenue Q | |
| 2003 | Denis O'Hare | Mason Marzac | Take Me Out |
| Kerry Butler | Penny Pingleton | Hairspray | |
| 2002 | Sam Robards | Gustav Eberson | The Man Who Had All The Luck |
| Anne Hathaway | Lil | Carnival | |
| 2001 | David Burtka | Boy | The Play About The Baby |
| Spencer Kayden | Little Sally | Urinetown | |
| 2000 | Derek Smith | The King Bastard | Green Bird King John |
| Sherie Rene Scott | Amneris | Aida | |
| 1999 | Robert Sella | Clifford | Side Man |
| Kristin Chenoweth | Sally Brown | You're A Good Man, Charlie Brown | |
| 1998 | Sam Trammell | The Son | Ah! Wilderness |
| Juliana Soelistyo | Golden Child | Golden Child | |
| 1997 | Alan Tudyk | Alan, Multiple Roles | Bunny, Bunny |
| Allison Janney | Liz Essendine | Present Laughter | |
| 1996 | Ruben Santiago Hudson | Canewell | Seven Guitars |
| Lisa Gay Hamilton | Veronica | Valley Song | |
| 1995 | Billy Crudup | The Tutor | Arcadia |
| Calista Flockhart | Laura | The Glass Menagerie | |
| 1994 | Robert Stanton | Various Roles | All In The Timing |
| Jeanne Paulen | Joleen Rowen | The Kentucky Cycle | |
| 1993 | Joe Mantello | Louis Ironson | Angels In America |
| Ann Dowd | Miss Proserpine Garnett | Candida | |
| 1992 | Patrick Fitzgerald | Sean O'Casey | Grandchild Of Kings |
| Tonya Pinkins | Anita | Jelly's Last Jam | |
| 1991 | Danny Gerard | Arty | Lost In Yonkers |
| James McDaniel | Paul Portier | Six Degrees Of Separation | |
| Jane Adams | Deirdre McDavey | I Hate Hamlet | |
| 1990 | Michael Jeter | Otto Kringelein | Grand Hotel |
| Mary-Louise Parker | Rita | Prelude To A Kiss | |
| 1989 | John Pankow | Eamon | Aristocrats |
| Mercedes Ruehl | Kate Sullivan | Other People's Money | |
| 1988 | B.D. Wong | Song Lilong | M. Butterfly |
| Christine Estabrook | Shelia | The Boys Next Door | |
| 1987 | Courtney B. Vance | Cory Maxson | Fences |
| Annette Bening | Holly Dancer | Costal Disturbances | |
| 1986 | John Mahoney | Artie Shaughnessy | The House Of Blue Leaves |
| Patti Cohenour | Rosa Bud | The Mystery Of Edwin Drood | |
| 1985 | Bill Sadler | Sgt. Merwin J. Tommey | Biloxi Blues |
| Joanna Gleason | Pam | A Day On The Death Of Joe Egg | |
| 1984 | Peter Gallagher | Billy | The Real Thing |
| Joan Allen | Hellen Stott | A Nightingale Sang | |
| 1983 | John Malkovich | Lee | True West |
| Dana Ivey | Monica Reed & Melanie Garth | Present Laughter & Quartermaine's Terms | |
| 1982 | Larry Riley | Private J. Memphis | A Soldier's Play |
| Joann Camp | Skye Bullene | Geniuses | |
| 1981 | Bob Gunton | 21 Characters | How I Got That Story |
| Mia Dillon | Babe Botrelle | Crimes Of The Heart | |
| 1980 | Eric Peterson | Billy Bishop | Billy Bishop Goes To War |
| Dianne Wiest | Elizabeth Barrow | On The Art Of Dining | |
| 1979 | Richard Cox | Dan Danger | Platinum |
| Laurie Kennedy | Voilet | Man And Superman | |
| 1978 | Morgan Freeman | Zeke | The Mighty Gents |
| Margaret Hilton | Eve | Molly | |
| 1977 | Barry Preston | The Eccentric Dance | Bubbling Brown Sugar |
| Rose Gregorio | Anges | The Shadow Box | |
| 1976 | Peter Evans | Richie | Streamers |
| Nancy Snyder | Joan of Arc | Knock, Knock | |
| 1975 | Reyno | Lou | The First Breexe Of Summer |
| Marybeth Hurt | Prue | Love For Love | |
| 1974 | Thom Christopher | Waiter | Noel Coward In 2 Keys |
| Ann Reinking | Maggie | Voer Here | |
| 1973 | Christopher Murney | Sylvester | Tricks |
| Mari Gorman | Jackie | Hot L Baltimore | |
| 1972 | Richard Backus | Wesley | Promenade All |
| Pamela Bellwood | Jill Tanner | Butterflies Are Free | |
| 1971 | James Woods | Lenny | Saved |
| Katherine Helmond | Bananas | The House Of Blue Leaves | |
| 1970 | Jeremiah Sullivan | Gravedigger | A Scent Of Flowers |
| Pamela Payton-Wright | Tillie | The Effect Of Gamma Rays On Man-In-The-Moon Marigolds | |
| 1969 | Ron O'Neal | Gabe | No Place To Be Somebody |
| Marlene Warfield | Discarded Mistress | The Great White Hope | |
| 1968 | David Birney | Troubled Youth | Summertree |
| Catherine Burns | Monica | The Prime Of Miss Jean Brodie | |
| 1967 | Austin Pendleton | Irwin Ingham | Hail Scrawdyke |
| Philip Bosco | Lincoln Center Rep | The Alchemist (Special Citation) | |
| Reva Rose | Lucy | You're A Good Man, Charlie Brown | |
| 1966 | Christopher Walken | King Phillip of France | The Lion In Winter |
| Tom Ahearne | Mayor | Hogan's Goat (Special Citation) | |
| Jean Hepple | Serving Girl | Sgt. Musgraves Dance | |
| 1965 | Jamie Sanchez | Jesus | Conerico Was Here To Stay |
| Elizabeth Hubbard | Monica | The Physicist | |
| 1964 | Richard McMurray | Magazine Editor | A Case Of Libel |
| Joyce Ebert | Andromache | The Trojan Women | |
| 1963 | Gene Hackman | Football Player | Children From Their Games |
| Jessica Walter | Secretary | Photo Finish | |
| 1962 | Gene Wilder | Dutch Hotel Valet | Complaisant Lover |
| Rebecca Drake | Helen Cobb | Who'll Save The Plowboy | |
| 1961 | Eric Christmas | Rector Olive | Little Moon Of Alba |
| Rosemary Murphy | Dorothea Bates | Period Of Adjustment | |
| 1960 | William Daniels | Peter | Zoo Story |
| Rochelle Oliver | Lily Berniers | Toys In The Attic | |
| 1959 | David Hurst | Police Inspector | Look After Lulu |
| Lois Nettleton | Shelia O'Conner | God & Kate Murphy | |
| 1958 | George C. Scott | Richard III | Richard III |
| Colin Wicox | Ellen Wells | The Day The Money Stopped | |
| 1957 | Ellis Rabb | Alceste | The Misanthrope |
| Joan Croydon | Housekeeper | The Potting Shed | |
| 1956 | Gerald Hiken | Telegen | Uncle Vanya |
| Frances Sternhagen | Shavian Heroine | The Admiral Bashville | |
| 1955 | Fritz Weaver | Flaminero | The White Devil |
| Vivian Nathan | Charwoman | Anastasia | |
| 1954 | David Lewis | Joe Wicks | King Of Hearts |
| Vilma Murer | Hilda Kranzbeck | The Winner | |
| 1953 | David J. Stewart | The Baron | Camino Real |
| Jenny Egan | Mary Warren | The Crucible | |
| 1952 | Iggie Wolfington | Chef | Mrs. Mcthing |
| Anne Meacham | Ensign Jane Hilton | The Long Watch | |
| 1951 | Logan Ramsey | Willie Pentridge | High Ground |
| Frederic Warriner | Soames | Getting Married | |
| Phyllis Love | Rose Delle Rose | The Rose Tattoo | |
| 1950 | Douglas Watson | Young Liberal | Wisteria Trees |
| Gloria Lane | Secretary | The Consul | |
| 1949 | Ray Walston | Traveling Salesman | Summer And Smoke |
| Leora Dana | Irma | The Madwoman Of Chaillot | |
| 1948 | Lou Gilbert | Charlie | Hope Is A Thing With Feathers |
| Catherine Ayers | Susie | Moon Of The Caribbean | |
| 1947 | Tom Ewell | Fred Taylor | John Loves Mary |
| Margaret Philips | Bridie Begtry | Another Part Of The Forest | |
| 1946 | Paul Douglas | Herry Brock | Born Yesterday |
| Barbara Bel Geddes | Genevra Langdon | Deep Are The Roots | |
| 1945 | Frederick O' Neal | Frank | Anna Lucasta |
| Judy Holliday | Alice | Kiss Them For Me |