1998-1999 45th Drama Desk Awards
| Outstanding One-Person Solo Performance | Will Bond (Bob) | |
| Alexander H. Cohen (Star Billing) | ||
| Aviva Jane Carlin (Jodie's Body) | ||
 |
David Hare (Via Dolorosa) | |
| Lisa Kron (2.5 Minute Ride) | ||
| Laurence Luckinbill (Clarence Darrow Tonight!) | ||
| Outstanding Actor - Musical | |
Brent Carver (Parade) |
| Martin Short (Little Me) | ||
| Patrick Wilson (Bright Lights Big City) | ||
| Tom Wopat (Annie Get Your Gun) | ||
| Outstanding Actor - Play | |
Brian Dennehy (Death of a Salesman) |
| Scott Glenn (Killer Joe) | ||
| Finbar Lynch (Not About Nightingales) | ||
| Corin Redgrave (Not About Nightingales) | ||
| Patrick Stewart (The Ride Down Mt. Morgan) | ||
| Toby Stephens (Ring Round the Moon) | ||
| Outstanding Actress - Musical | |
Carolee Carmello (Parade) |
| Bernadette Peters (Annie Get Your Gun) | ||
| Sian Phillips (Marlene Marlene) | ||
| Outstanding Actress - Play | Kathleen Chalfant (Wit)Zoe Wanamaker (Electra) | |
|
Judi Dench (Lindsay Duncan) | |
| Lindsay Duncan (Ashes to Ashes) | ||
| Elizabeth Franz (Death of a Salesman) | ||
| Swoosie Kurtz (The Mineola Twins) | ||
| Outstanding Choreography | Cabaret (Rob Marshall) | |
|
The Lion King (Garth Fagan) | |
| Luis Bravo's Forever Tango (The Forever Tango Dancers) | ||
| Ragtime (Graciela Daniele) | ||
| Outstanding Costume Design | Cabaret (William Ivey Long) | |
| Ivanov / Triumph of Love (Catherine Zuber) | ||
|
The Lion King (Julie Taymor) | |
| Luis Bravo's Forever Tango (Argemina Affonso) | ||
| Ragtime (Santo Loquasto) | ||
| Outstanding Director - Musical | Scott Ellis (1776) | |
| Frank Galati (Ragtime) | ||
| Sam Mendes, Rob Marshall (Cabaret) | ||
|
Julie Taymor (The Lion King) | |
| Outstanding Director - Play | Scott Elliot (Goose Pimples) | |
| James Houghton (The American Clock) | ||
| Garry Hynes (The Beauty Queen of Leenane) | ||
| Joe Mantello (Mizlansky/Zilinsky or Schmucks) | ||
|
Michael Mayer (A View from the Bridge) | |
| Simon McBurney (The Chairs) | ||
| Outstanding Featured Actor - Musical | Max Cassella (The Lion King) | |
|
Gregg Edelman (1776) | |
| Geoffrey Hoyle (The Lion King) | ||
| John McMartin (High Society) | ||
| Renoly Santiago (The Capeman) | ||
| Steven Sutcliffe (Ragtime) | ||
| Outstanding Featured Actor - Play | Ruaidhri Conroy (The Cripple of Inishman) | |
| Ron Liebman (A Dybbuk: Between Two Worlds) | ||
| Adam Alexi-Malle (Goose Pimples) | ||
|
Alfred Molina (Art / Ivanov) | |
| Max Wright (Ivanov) | ||
| Harris Yulin (The Diary of Anne Frank) | ||
| Outstanding Featured Actress - Play | Patricia Clarkson (The Maiden's Prayer / A View from the Bridge) | |
|
Allison Janney (TA View from the Bridge) | |
| Linda Lavin (The Diary of Anne Frank) | ||
| Patti LuPone (The Old Neighborhood) | ||
| Marian Seldes (Ivanov) | ||
| Caroline Seymour (Goose Pimples) | ||
| Outstanding Featured Actress - Musical | Betty Buckley (Triumph of Love) | |
| Lea DeLaria (On the Town) | ||
| Anna Kendrick (High Society) | ||
|
Tsidii Le Loka (The Lion King) | |
| Ednita Nazario (The Capeman) | ||
| Michele Pawk (Cabaret) | ||
| Outstanding Lighting Design | Ballad of Yachiyo (Peter Maradudin) | |
| Cabaret (Peggy Eisenhauer, Mike Baldassari) | ||
| The Chairs (Paul Anderson) | ||
|
The Lion King (Donald Holder) | |
| Pride's Crossing / A View from the Bridge (Kenneth Posner) | ||
| Ragtime (Jules Fisher, Peggy Eisenhauer) | ||
| Outstanding Lyrics | Hedgwig and the Angry Inch (Stephen Trask) | |
|
Ragtime (Lynn Ahrens) | |
| Triumph of Love (Susan Birkenhead) | ||
| Outstanding Music | The Capeman (Paul Simon) | |
| Hedwig and the Angry Inch (Stephen Trask) | ||
|
Ragtime (Stephen Flaherty) | |
| The Scarlet Pimpernel (Frank Wildhorn) | ||
| Outstanding Musical | Hedwig and the Angry Inch | |
| High Society | ||
| The Lion King | ||
| Luis Bravo's Forever Tango | ||
|
Ragtime | |
| Outstanding Orchestrations | Lisandro Adrover (Luis Bravo's Forever Tango) | |
|
William David Brohn (Ragtime) | |
| Bruce Coughlin (The Sound of Music) | ||
| Robert Elhai, David Metzger, Bruce Fowler (The Lion King) | ||
| Michael Gibson (Cabaret) | ||
| Stanley Silverman (The Capeman) | ||
| Outstanding Play | Art (Yasmina Reza) | |
| As Bees in Honey Drown (Douglas Carter Beane) | ||
|
The Beauty Queen of Leenane (Martin McDonough) | |
| Collected Stories (Donald Margulies) | ||
| Side Man (Warren Leight) | ||
| Three Days of Rain (Richard Greenberg) | ||
| Outstanding Puppet Design | Ballad of Yachiyo (Bruce Schwartz) | |
| Jackie: An American Life (The Big Nazo Studio) | ||
|
The Lion King (Julie Taymor, Michael Curry) | |
| Tell Tale (Basil Twist) | ||
| Outstanding Revival-Musical | |
1776 |
| Cabaret | ||
| Outstanding Revival-Play | All My Sons (Arthur Miller) | |
| The American Clock (Arthur Miller) | ||
| The Chairs (Eugene Ionesco) | ||
| Ivanov (Anton Chekhov) | ||
| A View from the Bridge (Arthur Miller) | ||
| Outstanding Set Design - Musical | Cabaret (Robert Brill) | |
|
The Lion King (Richard Hudson) | |
| Ragtime (Eugene Lee, Wendell K. Harrington) | ||
| Outstanding Set Design - Play | Ballad of Yachiyo (Loy Arcenas) | |
|
The Chairs (The Quay Brothers) | |
| Ivanov (John Lee Beatty) | ||
| Misalliance (Derek McLane) | ||
| Mizlansky/Zilinsky or "schmucks" (Santo Loquasto) | ||
| Three Days of Rain (Chris Barreca) | ||
| Outstanding Sound Design | The Chairs (Paul Arditti) | |
|
The Lion King (Tony Meola) | |
| Mamba's Daughters (Thomas Cabannis) | ||
| Scotland Road (David Van Tieghem) | ||
| Therese Raquin (Rinde Eckert, Gina Leishman) | ||
| The View from the Bridge (Mark Bennett) | ||
| Special Awards | |
Arthur Miller |
|
The Vineyard Theatre |
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