The Drama Desk Award for Outstanding Direction of a Play is an annual award presented by Drama Desk in recognition of achievements by theatre directors across collective Broadway, off-Broadway, and off-off-Broadway productions in New York City, United States. The awards were established in 1955, with the Drama Desk Award for Outstanding Director being presented each year to a director from any play or musical production. Starting in 1975, the singular director's award was replaced by separate play and musical categories.
Jack O'Brien and Jerry Zaks hold the record for most wins in the category, with three each. Daniel J. Sullivan holds the record for most nominations, with seven, followed closely by Joe Mantello with six and Mike Nichols with five. Mary Zimmerman was the first female winner, receiving the award in 2002 for Metamorphoses. Since her win, Anna D. Shapiro, Pam MacKinnon, Marianne Elliott, Rebecca Frecknall and current winner Danya Taymor have also won the award as female directors.
Winners and nominees Key
1970s Year Director Production 1975 John Dexter Equus |- | Frank Dunlop | Sherlock Holmes |- | rowspan="2"| Athol Fugard | Sizwe Banzi Is Dead |- | The Island |- | Peter H. Hunt | Goodtime Charlie |- | Ron Link | Women Behind Bars |- | Gene Saks | Same Time, Next Year |- ! rowspan="7" align="center"| 1976 |- style="background:#DCEEFF" | Ellis Rabb| The Royal Family |- | Edward Albee | Who's Afraid of Virginia Woolf? |- | Arvin Brown | Dual Bill |- | Mike Nichols | Streamers |- | Stephen Porter | They Knew What They Wanted |- | Tom Signorelli | Lamppost Reunion |- ! rowspan="7" align="center"| 1977 |- style="background:#DCEEFF" | Mike Nichols| Comedians |- style="background:#DCEEFF" | Alan Schneider| A Texas Trilogy Frank Dunlop The New York Idea Tony Giordano G.R. Point Ulu Grosbard American Buffalo Oz Scott For Colored Girls Who Have Considered Suicide When the Rainbow Is Enuf 1978 Melvin Bernhardt Da Peter Bennett Dracula Joseph Chaikin The Dybbuk Mike Nichols The Gin Game Steven Robman Uncommon Women Garland Wright K 1979 Jack Hofsiss The Elephant Man Alan Ayckbourn Bedroom Farce John Madden Wings Stephen Porter Man and Superman Horacena J. Taylor Nevis Mt. Dew Ted Weiant The Miracle Worker
1980s Year Director Production 1980 Vivian Matalon Morning's at Seven |- | Kevin Conway | Mecca |- | Gordon Davidson | Children of a Lesser God |- | Lynne Gannaway and Robert Kalfin | Strider |- | Marshall W. Mason | Talley's Folly |- | Alan Schneider | Loose Ends |- ! rowspan="5" align="center"| 1981 |- style="background:#DCEEFF" | Peter Hall| Amadeus |- | Melvin Bernhardt | Crimes of the Heart |- | Geraldine Fitzgerald | Mass Appeal |- | Douglas Seale | The Winslow Boy |- ! rowspan="6" align="center"| 1982 |- style="background:#DCEEFF" | Tommy Tune| Cloud Nine Athol Fugard "Master Harold"...and the Boys Jacques Levy Potsdam Quartet John Tillinger Entertaining Mr Sloane Douglas Turner Ward A Soldier's Play 1983 Trevor Nunn All's Well That Ends Well |- | Robert Allan Ackerman | Extremities |- | Michael Bennett | Third Street |- | George C. Scott | Present Laughter |- | Arthur Sherman | The Caine Mutiny Court-Martial |- | Gary Sinise | True West |- ! rowspan="7" align="center"| 1984 |- style="background:#DCEEFF" | Michael Blakemore| Noises Off |- | Lee Grant | A Private View |- | Gerald Gutierrez | Isn't It Romantic |- | Terry Kinney | And a Nightingale Sang |- | Gregory Mosher | Glengarry Glen Ross |- | Mike Nichols | The Real Thing |- ! rowspan="6" align="center"| 1985 |- style="background:#DCEEFF" | John Malkovich| Balm in Gilead Ron Lagomarsino Digby Marshall W. Mason As Is Gene Saks Biloxi Blues Claudia Weill Found a Peanut 1986 Jerry Zaks The Marriage of Bette & Boo The House of Blue Leaves Liviu Ciulei Hamlet Jonathan Miller Long Day's Journey into Night Mary B. Robinson Lemon Sky Gary Sinise Orphans John Tillinger It's Only a Play Loot 1987 Howard Davies Les Liaisons Dangereuses Simon Gray and Michael McGuire The Common Pursuit Ron Lagomarsino Driving Miss Daisy Lloyd Richards Fences Carole Rothman Coastal Disturbances Gene Saks Broadway Bound 1988 John Dexter M. Butterfly W. H. Macy Boys' Life Lynne Meadow Woman in Mind Gregory Mosher Speed-the-Plow Lloyd Richards Joe Turner's Come and Gone 1989 Jerry Zaks Lend Me a Tenor Simon Callow Shirley Valentine Robin Lefèvre Aristocrats Jack O'Brien The Cocktail Hour Norman René Reckless Daniel Sullivan The Heidi Chronicles
1990s Year Director Production 1990 Frank Galati The Grapes of Wrath |- | Roger Michell | Some Americans Abroad |- | Adrian Noble | The Art of Success |- | Norman René | Prelude to a Kiss |- | Lloyd Richards | The Piano Lesson |- ! rowspan="5" align="center"| 1991 |- style="background:#DCEEFF" | Jerry Zaks| Six Degrees of Separation |- | Michael Greif | Machinal |- | Richard Jones | La Bête |- | Kevin Kline | Hamlet |- ! rowspan="6" align="center"| 1992 |- style="background:#DCEEFF" | Patrick Mason| Dancing at Lughnasa |- | JoAnne Akalaitis | 'Tis Pity She's a Whore |- | Michael Bloom | Sight Unseen |- | David Chambers | Search and Destroy |- | Mark Wing-Davey | Mad Forest |- ! rowspan="6" align="center"| 1993 |- style="background:#DCEEFF" | George C. Wolfe| Angels in America: Millennium Approaches |- | Christopher Ashley | Jeffrey |- | Adrian Hall | As You Like It |- | Ariane Mnouchkine | Les Atrides |- | Daniel Sullivan | The Sisters Rosensweig |- ! rowspan="6" align="center"| 1994 |- style="background:#DCEEFF" | Stephen Daldry| An Inspector Calls |- | JoAnne Akalaitis | In the Summer House |- | Jonathan Kent | Medea |- | Mark Wing-Davey | The Lights |- | Mary Zimmerman | Arabian Nights |- ! rowspan="7" align="center"| 1995 |- style="background:#DCEEFF" | Gerald Gutierrez| The Heiress |- | Declan Donnellan | As You Like It |- | David Esbjornson | Iphigenia and Other Daughters |- | Emily Mann | Having Our Say |- | Joe Mantello | Love! Valour! Compassion! |- | Sean Mathias | Indiscretions |- ! rowspan="7" align="center"| 1996 |- style="background:#DCEEFF" | Gerald Gutierrez| A Delicate Balance |- | Scott Elliott | The Monogamist |- | Doug Hughes | The Grey Zone |- | Adrian Noble | A Midsummer Night's Dream |- | Lloyd Richards | Seven Guitars |- | George C. Wolfe | The Tempest |- ! rowspan="6" align="center"| 1997 |- style="background:#DCEEFF" | Mark Brokaw| How I Learned to Drive Robert La Page The Seven Streams of the River Ota Lynne Meadow Nine Armenians Deborah Warner The Waste Land Mark Wing-Davey The Skriker 1998 Michael Mayer A View from the Bridge |- style="background:#DCEEFF" | Side Man Scott Elliott Goose-Pimples James Houghton The American Clock Garry Hynes The Beauty Queen of Leenane Joe Mantello Mizlansky/Zilinsky or 'Schmucks|- | Simon McBurney | The Chairs |- ! rowspan="7" align="center"| 1999 |- style="background:#DCEEFF" | Trevor Nunn| Not About Nightingales ''' |- | Derek Anson Jones | Wit|- | Howard Davies | The Iceman Cometh |- | Robert Falls | Death of a Salesman |- | Patrick Marber | Closer|- | Nicholas Martin | Betty's Summer Vacation''
2000s Year Director Production 2000 Michael Blakemore Copenhagen Thomas Hulce and Jane Jones The Cider House Rules (Part One) James Lapine Dirty Blonde Michael Mayer Uncle Vanya Marion McClinton Jitney Daniel J. Sullivan Dinner with Friends 2001 Jack O'Brien The Invention of Love Mark Brokaw Lobby Hero Michael Greif Dogeaters Philip Seymour Hoffman Jesus Hopped the 'A' Train Jonathan Kent Richard II Matthew Warchus The Unexpected Man 2002 Mary Zimmerman Metamorphoses Howard Davies Private Lives Richard Eyre The Crucible Carl Forsman The Voice of the Turtle Neil LaBute The Shape of Things Bartlett Sher Cymbeline 2003 Robert Falls Long Day's Journey into Night Philip Seymour Hoffman Our Lady of 121st Street Joe Mantello Take Me Out Sam Mendes Twelfth Night Uncle Vanya Deborah Warner Medea 2004 Jack O'Brien Henry IV Hilary Adams Moby Dick Dexter Bullard Bug Edward Hall A Midsummer Night's Dream Moisés Kaufman I Am My Own Wife Kenny Leon A Raisin in the Sun 2005 Doug Hughes Doubt Josh Carlebach Frankenstein Scott Elliott Hurlyburly Scott Ellis Twelve Angry Men Edward Hall Rose Rage Joe Mantello Glengarry Glen Ross 2006 Nicholas Hytner The History Boys Alan Ayckbourn Private Fears in Public Places Gisela Cardenas Agamemnon Daniel J. Sullivan Stuff Happens Robert Wilson Peer Gynt Jerry Zaks The Caine Mutiny Court-Martial 2007 Jack O'Brien The Coast of Utopia Declan Donnellan Twelfth Night Michael Grandage Frost/Nixon Doug Hughes Inherit the Wind Ciaran O'Reilly The Hairy Ape Tom Ridgely Marco Millions 2008 Anna D. Shapiro August: Osage County David Schweizer HorizonLeigh Silverman From Up Here Jonathan Silverstein The Dining Room Matthew Warchus Boeing-Boeing Deborah Warner Happy Days 2009 Matthew Warchus The Norman Conquests Sarah Benson Blasted Michael Blakemore Blithe Spirit Garry Hynes The Cripple of Inishmaan Terry Kinney reasons to be pretty Kate Whoriskey Ruined
2010s Year Director Production 2010 Michael Grandage Red |- | Jonathan Bank | So Help Me God! |- | Jack Cummings III | The Boys in the Band |- | Sam Gold | Circle Mirror Transformation |- | Michael Grandage | Hamlet |- | Ethan Hawke | A Lie of the Mind |- ! rowspan="7" align="center"| 2011 |- style="background:#DCEEFF" | Joel Grey and George C. Wolfe| The Normal Heart |- | Trip Cullman | A Small Fire |- | Moisés Kaufman | Bengal Tiger at the Baghdad Zoo |- | Davis McCallum | A Bright New Boise |- | Daniel J. Sullivan | The Merchant of Venice |- | Kirjan Waage and Gwendolyn Warnock | Baby Universe |- ! rowspan="7" align="center"| 2012 |- style="background:#DCEEFF" | Mike Nichols| Death of a Salesman |- | Jo Bonney | By the Way, Meet Vera Stark |- | David Cromer | Tribes |- | Ed Sylvanus Iskandar | These Seven Sicknesses |- | Sam Mendes | Richard III |- | Tony Speciale | Unnatural Acts |- ! rowspan="7" align="center"| 2013 |- style="background:#DCEEFF" | Pam MacKinnon| Who's Afraid of Virginia Woolf? |- | Lear deBessonet | The Good Person of Szechwan |- | Sam Gold | Uncle Vanya |- | Ed Sylvanus Iskandar | Restoration Comedy |- | Lynne Meadow | The Assembled Parties |- | Ruben Santiago-Hudson | The Piano Lesson |- ! rowspan="7" align="center"| 2014 |- style="background:#DCEEFF" | Tim Carroll| Twelfth Night |- | Joe Calarco | A Christmas Carol |- | Thomas Kail | Family Furniture |- | Bill Rauch | All the Way |- | Anna D. Shapiro | Domesticated |- | Julie Taymor | A Midsummer Night's Dream |- ! rowspan="8" align="center"| 2015 |- style="background:#DCEEFF" | Marianne Elliott| The Curious Incident of the Dog in the Night-Time Jeremy Herrin Wolf Hall Parts One & Two Anne Kauffman You Got OlderLila Neugebauer The Wayside Motor Inn Austin Pendleton Between Riverside and Crazy Joe Tantalo Deliverance John Tiffany Let the Right One In 2016 Ivo van Hove A View from the Bridge Rachel Chavkin The Royale Sam Gold John Rupert Goold King Charles III Joe Mantello The Humans Jenn Thompson Women Without Men2017Ruben Santiago-HudsonJitney Anne KauffmanA LifeRichard NelsonWhat Did You Expect? and Women of a Certain AgeDaniel J. SullivanThe Little Foxes If I Forget2018John TiffanyHarry Potter and the Cursed Child Marianne ElliottAngels in America Jeremy HerrinPeople, Places and ThingsJoe MantelloThree Tall Women Lila NeugebauerMiles for MarySimon StoneYerma2019Sam MendesThe Ferryman Sarah BensonFairviewStephen Daldry and Justin MartinThe JungleTyne RafaeliUsual GirlsTaylor ReynoldsPlanoJeff WiseLife Sucks
2020s